There’s a reason why New England is world-famous for fall foliage, and if you’re looking to plan the most amazing New England fall road trip, you’ve come to the right place! I’ve been traveling throughout this region for over 15 years, and have done so many fall foliage road trips and getaways in that time. It took me a while, but I’ve finally put together the perfect itinerary for you based on years of real experience.
This post details the best places to visit in New England during fall foliage season that are worth the hype (and your time), the best times to plan your road trip for peak foliage, and also, which places may not be worth your time. So, you can rest assured that you’re truly seeing the best of the best with my itinerary.
This itinerary is also geared toward first-timers and those looking to find the best foliage spots. If you’ve experienced New England in the fall season before, many of these locations and tips may already be familiar. However, I’ve also sprinkled in some insider tips, so it’s still definitely worth reading π
During this trip, prepare to see idyllic countryside landscapes, blazing fall color, beautiful covered bridges, charming towns, general stores, epic overlooks and hiking trails, and so much more. Basically, you’ll get your fill of New England charm right from the start, and it won’t stop until the trip is over. Sound good? Then let’s get started!
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What Is The Best Time To Visit New England For Fall Color?
In a nutshell, the first two weeks of October.
However, it does vary depending on where you’re heading.
The first thing you need to know is that foliage will peak in the northern areas first, then peak in the southern areas later. For that reason, I recommend that you start in the north if you can, especially for a longer trip, but it’s not always necessary for shorter trips.
If you’re planning a bucket list 2 or 3-week adventure, starting in the north is a good call because peak foliage can begin to diminish quickly, depending on the season and climate patterns. However, if you’re traveling for closer to a week, this won’t be as important, as you can time your visit right for the areas you want to see.
Most people will choose to visit Massachusetts, New Hampshire and Vermont during their New England fall road trip (and spoiler alert: I’ll be suggesting these places, too π), and the first two weeks of October work very well for these destinations.
The central part of Vermont will often peak right around Indigenous People’s weekend in October, and for a getaway to popular towns like Stowe and Woodstock, this is the perfect weekend to plan your trip.
The Berkshires in Massachusetts often peaks right around Indigenous People’s weekend as well, with southern MA peaking a week or so later.
Many parts of Maine, including Acadia National Park, and the Midcoast, will typically peak around the middle of October.
The greater Boston area, and Connecticut will peak mid-late October, depending on the year.
How Many Days Do You Need In New England In The Fall?
The great thing about New England in the fall is that you can easily do a weekend getaway and still pack a lot in, or you can plan an epic 2 or 3 week road trip for the ultimate adventure. And either way, it’s going to be incredibly memorable.
If you’re coming in from a distance, especially if you’re flying in, I would say 10 days is a great option, 12 days is even better, and 7 days is also wonderful. Of course, with 12 days, you’ll be able to see so much or plan extra time in some places. But even with 7 days, you’ll get to see quite a bit.
However, I always say more is always more when it comes to travel! So of course, three weeks to see all the fall foliage around New England is the ultimate goal, however, I know that’s not realistic for everyone, which is why I think 7-12 days is a great sweet spot.
If you’re local to New England, and don’t have 10 days, 7 days is again a nice amount of time. Five days will also work in this case. And, as mentioned, even a weekend away will allow you to experience some of the best this region has to offer in the fall season.
The great thing about the best places for fall foliage is that they’re located in some of the smallest states, so you can cover a lot of ground in a short amount of time.
Best Places To See On A New England Fall Road Trip
While every New England state has something special to offer during fall foliage season, for the purpose of seeing the absolute best, brightest, and most abundant colors, I recommend planning a trip to Maine, Massachusetts, New Hampshire, Vermont, and Connecticut (if you have the time). However, to narrow that down even further, New Hampshire and Vermont are definitely the best to visit if you’re short on time.
So, why these areas?
Because they offer the most spectacular displays of foliage, the most picturesque scenery, tons of things to do, and they’re all reasonably close to one another, allowing you to maximize your time.
If you don’t have a lot of time for your road trip, I usually suggest Connecticut is the first state to remove from your list, and the reason for that is because it’s so far west, and further from many of the other top destinations.
I also don’t recommend visiting places in Rhode Island during your fall foliage road trip simply because you won’t see the most amazing displays of color (I love Rhode Island, but it’s not really known for its epic fall foliage).
Some Things To Know About This Itinerary:
β They all begin in Boston, assuming that’s where most people will fly into if visiting from a distance. If you fly into a different airport, or are driving in, you can easily adjust your plans as needed. However, Boston has its own cozy fall vibes that are in full swing mid to late October, so it’s truly the best place to start your fall foliage adventure.
β They’re done in true road trip style, meaning there’s a lot of driving, and mostly 1-night stays. There are some places I recommend 2 nights in, but you can adjust this based on your preferences. If you want to stay longer in one place, definitely go for it!
β I planned the order of the stops according to how fall foliage peaks, meaning you’ll be starting in the north, and working your way down. However, since there are so many areas to see, it’s not always possible to see very region right at peak, so you’ll be just a bit early, or late, for some places, depending on your exact dates. For example, if you want to see the White Mountains in New Hampshire at peak time, which is usually the first week in October, you likely won’t get to see Connecticut at peak, since that’s usually the third week of October – unless of course you can travel for three weeks, which is awesome!
β I give you options! Of course, I stand by all my suggestions π However, I know everyone has different travel styles and speeds, so I encourage you to to tailor this to what you think you’ll enjoy the most. I’ve given you suggestions on how to adjust the itinerary based on your preferences.
10 Day New England Fall Road Trip Itinerary From Boston
Okay, let’s get into my PERFECT New England fall road trip itinerary options!
We’re beginning with my suggestions for an incredible 10 day adventure.
10 Day Road Trip Overview:
Day 1: Arrival In Boston, drive to the Franconia side of the White Mountains in New Hampshire
Day 2: Explore the White Mountains region, including The Kancamagus Highway
Day 3: Drive to Stowe, VT, and stay here or nearby for two nights
Day 4: Explore central Vermont (I have great suggestions for you!)
Day 5: Drive to southern Vermont, and spend one night around the Manchester area
Day 6: Drive to The Berkshires for one night
Day 7: Drive to the Litchfield Hills region of CT, spend one night
Day 8: Drive to Salem, MA for one night
Day 9: See more of Salem or the North Shore in the morning, then drive to Boston for one night
Day 10: Spend the day exploring Boston.
The Day By Day Breakdown Of The 10 Day Itinerary – Let’s Go!
Days 1-2: Arrival In Boston & Two Nights In The White Mountains, New Hampshire
Once you arrive in Boston, it’s time to hit the ground running and make the drive to the White Mountains in New Hampshire! Since this region is one of the earlier ones to peak, you’ll want to make this the first stop on your New England fall foliage road trip.
The drive from Boston to the White Mountains is about 2.5-3 hours, depending on traffic getting out of the city, and where in the White Mountains you want to stay.
Where To Stay In The White Mountains: I have an entire guide on the best places to stay in the White Mountains, so that’s a good read to check out while planning your trip π I would pick one place to stay for both nights, as some places have a two-night minimum in the fall season. This region is also small enough that you can see it all when staying in one place.
Here are some of my favorite hotels in the White Mountains:
π Sugar Hill Inn – 15 mins from Franconia Notch Park, and is rated as the best B&B in New Hampshire!
π Riverwalk Resort – 5-7 mins from the top attractions in Franconia.
π Woodstock Inn & Brewery – Cozy inn with a brewery.
Best Things To Do In The White Mountains In The Fall:
β Explore Franconia Notch State Park, which is home to quite a few things to do, which I’ll list out next for you. Even the drive through the park is going to offer you incredible foliage views!
β Flume Gorge inside Franconia Notch State Park. This is a 2-mile trail that meanders over covered bridges in the woods, and through a natural gorge that’s such a cool thing to experience. You’ll also be treated to some stunning foliage views of the mountains along the way. I have a detailed post all about visiting Flume Gorge, if you’d like to take a peek. This will have everything you need to know about tickets, tips for planning your visit, and what to expect.
β Ride the Cannon Mountain Aerial Tramway, which is the first of its kind in North America! This ride takes you to the summit where you can enjoy stunning views of the surrounding mountain vistas. Fall is my favorite time of year to do this. I also have a detailed post on things to know about the Cannon Mountain Aerial Tramway, if you want to check that out.
β Hike the Artist Bluff trail in Franconia. This is now a very popular trail in the area, and while the views are so worth it, I’d most definitely recommend you do this one at sunrise or sunset to avoid as many crowds as possible.
β Drive the famous Kancamagus Highway, which is one of the most scenic fall foliage drives in the northeast! This highway is free to drive, and connects the towns of Lincoln and Conway along Route 112 through the White Mountains National Forest. During the drive, you’ll see amazing mountain views, and colorful trees dripping in fall color lining the side of the road, so you get the best of both words. See below for my tips and things you need to know about driving The Kanc (as the locals call it π).
β Drive through Crawford Notch State Park to be rewarded with more stunning views of the mountains ablaze with foliage color!
β Visit two of the most charming towns in the area: Littleton and North Conway. Littleton is widely regarded for having one of the best Main Streets in the U.S., and you’ll find a brewery, covered bridge, and quaint shops downtown. In North Conway, the main road runs through the town, but there are some gorgeous views to enjoy, great shops, and don’t miss Zeb’s General Store!
β Take a ride on The Cog to the highest peak in New England – Mount Washington. This mountain railway is such a cool experience! While foliage will likely be gone toward the top of the mountain by early October, you’ll still get some nice foliage color on the way up, and enjoy incredible views from the top!
β Drive to the Cathedral Ledge Lookout, which offers really awesome views, especially in the fall.
I have some more detailed posts on this region of New Hampshire you may find helpful:
- Fun Things To Do In Franconia, NH
- Fun Things To Do In Littleton, NH
- Fun Things To Do In Lincoln, NH
- Where To Stay In New Hampshire In The Fall
Tips for driving The Kanc:
β There is no cell service, or gas stations along the drive, so be sure you’re prepared. You’ll want to offline maps to your phone before heading out, and while the drive is only about 34 miles long, just make sure you have enough gas to make the whole drive.
β There are some bathroom facilities at some of the parking areas, but not many. It may not be a good idea to fill up on coffee or water at the start of the drive.
β There are tons of places to pull over on the drive, including quick, but scenic overlooks, and parking lots for trailhead to hikes and such. Besides the overlooks, my favorite stops to make is the Lincoln Woods Trailhead, which after a very short walk from the parking area, has a really pretty bridge that makes for a great photo.
β You’ll need to pay a daily fee to park in any of the lots along the drive (these are separate from the designated overlooks). Be sure to find the kiosks when you park for the first time, and keep that ticket displayed on your dashboard the rest of the drive. You only need to pay once, and your ticket is good for the entire day. If you don’t plan to park in the lots along the drive, you don’t need to pay.
β On the Conway side of The Kanc, there’s a great little place called Cheese Louise just before the entrance to drive. This is an awesome place to grab some food before or after the drive! Especially on a chilly, fall day, a grilled cheese sandwich totally hits the spot, right?
π Before hopping on The Kanc,
consider downloading this great audio tour so you don’t miss the best stops to make –
Click here to check out this audio tour
Days 3 & 4: Drive To Stowe, Spend Two Day Exploring Central Vermont
Next up is Vermont! The drive from the White Mountains to Stowe, VT is about 1.5-2.5 hours, depending on where in the White Mountains you came from.
The central region of Vermont is one of the absolute best places for fall foliage in New England, and places like Stowe, Woodstock, and the surrounding countryside are going to give you all the postcard-worthy scenery youβve been hoping for. I also love Vermont because it has more of a New England vibe than the White Mountains, so youβll also get some of the charm the Northeast is known for.
Where to stay in Central Vermont: I recommend that you stay in or around Stowe or Woodstock because both of these towns have lots to do in their own right, great hotels to choose from, wonderful dining options, and theyβre only about 1.5 from one another. Both are charming towns, and you canβt go wrong with either.
Where To Stay In Stowe:
π The Green Mountain Inn. It’s located right on Main Street, so you can walk to a lot of places.
π Spruce Peak Resort. Perfect for those wanting a resort feel, and it’s right off the scenic Smugglers Notch drive. There are rooms with gorgeous mountain views here, too.
Where To Stay In Woodstock:
π 506 Inn On The River. Located just outside of the village, this is a modern and cozy inn, well … right on the river
π The Woodstock Inn & Resort. It’s referred to as Vermont’s most beautiful address, and it’s in the heart of Woodstock’s village. This is a luxury hotel that’s worth it!
Noteworthy stops to make on the way to Stowe: If you have the time, there are some absolutely beautiful places to check out in the countryside on this drive. Most of them require a little detour, but gosh, theyβre so worth it! Iβve listed them down below for you:
β Peachum, VT, which is a very small, rural community, but the foliage views around here are like literal postcards.
β Danville to do the Great Vermont Corn Maze, which is the largest in New England. Itβs so big that youβll need a couple of hours here, but itβs a very fun experience. Keep in mind that itβs only open until mid-October – be sure to check their website or Facebook page for updated info.
β The Owls Head Mountain Hike in Groton State Forest. This is a relatively easy hike that takes you to an incredible view overlooking Lake Groton and Kettle Pond – itβs even better in the fall season!
β Bogie Farm in East Ryegate is a landscape thatβs worthy of a postcard, and is especially beautiful in the fall. Please be respectful of the farm’s property, and enjoy the views from a respectful distance π
Best Things To Do In Stowe, VT In The Fall:
β Drive Smugglers Notch, which is a short but scenic drive through mountains, and offers incredible opportunities to see fall color.
β Stop at the Stowe Gondola along the Smugglers Notch drive, and take a gondola ride to the top of the tallest peak in Vermont – Mount Mansfield.
β Explore the charming downtown along Main Street, which has great shops, cafΓ©s, foliage views, and access to the Recreation Path.
β Be sure to walk the Recreation Path, which is a paved pedestrian path that runs through town, and depending on how much of it you walk, youβll cross pretty bridges (one of which is the Brookdale Covered Bridge!), and enjoy some more peaceful moments.
β Visit Gold Brook Covered Bridge, which is also known as Emilyβs Bridge. This bridge is said to be haunted, so itβs the perfect spooky season photo opp! Please just practice caution and respect while visiting, as itβs a bridge thatβs still used by the locals – definitely donβt block traffic by standing in the middle of the road!
β Take a drive to Waterbury, which is home to Cold Hollow Cider Mill, Ben & Jerryβs, and the Cabot Cheese Farmerβs Store (which has samples, yum!). This area gets extremely backed-up with traffic in the fall season, so if this is something that will bother you, I recommend taking a scenic drive out to Burtt’s Orchards, which is just under an hour from Stowe. They have delicious cider donuts that I actually prefer over Cold Hollow’s, and you can also visit AM Foster Covered Bridge nearby. I love both areas, but like to paint an accurate picture for you, so you can decide for yourself which is best for your plans!
β Visit Stowe Cider, which is just perfect during the fall season.
Best Things To Do In Woodstock, VT In The Fall:
β Walk around the charming village, which is lined with fall foliage trees, and awesome fall decorations.
β Snap a photo with Middle Covered Bridge, which is located right in the village.
β Take a drive to Sugarbush Farms, which has amazing mountain views that are at their best in the fall season, and sample their maple syrup and cheeses! The drive out here is on a bumpy dirt road, so drive slowly.
β Visiting Billings Farm & Museum, which is a working dairy farm and museum, and is such a wonderful place to experience.
β Visit the townβs other two covered bridges: Taftsville and Lincoln.
β Take a drive to nearby Quechee, which is home to the awesome Canopy Walk at VINS, Quechee Gorge, and the very cool and unique Quechee Village Shopping Center.
β Get a maple creemee around the village – this is Vermontβs version of soft serve ice cream, but itβs infused with local maple syrup, which is especially delightful in the fall season.
Psst! I have detailed posts on both Stowe and Woodstock, if you want to check those out:
Important Note About Visiting Stowe In The Fall Season: Stowe is one of the the most popular places to visit in Vermont in the fall season, so you’ll want to anticipate crowds and heavy traffic. Traffic gets extremely backed up getting in and out of town this time of the year. Since Stowe is a very small place, and wasn’t built to accommodate the amount of tourism it gets in the fall season, traffic can experience significant slow-downs, especially on weekends. This is largely due to congestion from folks trying to turn in and out of Cold Hollow Cider Mill on Waterbury-Stowe Road, just outside of town. It’s a good idea to plan accordingly, or try to arrive early in the morning.
Woodstock also gets pretty busy, with lots of people everywhere, especially on weekends. Traffic doesn’t get as congested, as the town’s roads are more conducive to high tourism, but this is also something to be aware of!
Day 5: Drive To Southern Vermont, Spend One Night
Once youβve explored Central Vermont, itβs time to head a bit further south. And the reason I recommend you split up your time in Vermont is because this region is so worth seeing in the fall, but itβs just far away enough where it makes sense to spend a night here.
There are also quite a few hotels around the Manchester area, so youβll have an easier time finding places to stay that donβt require a 2-night minimum, which is harder to do up in Stowe and Woodstock.
If you happen to visit Stock and Woodstock during peak foliage, it’s possible that you’ll hit this region just as peak is beginning, but it really depends on quickly it moves that year. Just know there’s a chance you’ll be a bit early, but keep in mind that even if you’re a tad early for peak foliage in Vermont, you’ll still see a good amount of color.
Southern Vermont is just as idyllic as the Stowe and Woodstock regions, and gosh, youβll have a great time leaf-peeing here, too! I recommend you spend most of your time in the Manchester area, but there are a few places within a short drive that are perfect for spotting gorgeous foliage.
Where to stay in Southern Vermont: There are lots of great places to stay in this region, including in Manchester, Bennington, and the more rural towns like Sunderland. I would pick which hotel you like the most, as all my recommended things to do are a short drive away from each of these places.
Hotels I Love In Southern Vermont:
π Hill Farm Inn: Absolutely incredible property in the countryside, with on-site dining in a barn, cozy rooms, and mountain views from their porch.
π Kimpton Taconic: Beautiful rooms and a boutique-style hotel, located in Manchester.
π Four Chimneys: One of the best inns in Southern Vermont, located in Bennington.
Notable stops to make on the way to Southern Vermont:
β I suggest taking the Route 100 option, which only adds a few minutes to the drive.
β If you stayed in Stowe, and didn’t make it to Woodstock, this route will pass close by Woodstock, so you could stop here for a few hours on your way to Manchester.
β The Plymouth Cheese Shop on the way is a fun place to stop for samples, and buy cheeses to take home! There’s also really pretty foliage around here.
β Weston to stop at the Vermont Country Store, which is a huge general store with tons of awesome goodies.
Best Things To Do In The Manchester, VT Area In The Fall:
β Drive the Mt. Equinox Skyline Road to the top of the mountain, which is the tallest in the Taconic Mountain range! The foliage views are incredible up this way (if you can time your visit right), and itβs such a fun experience. There is a fee to drive this road, so plan accordingly.
β Visit Hildene, The Lincoln Family Home. This historic estate is cool to see on its own, but the views of the mountains from the back gardens are what makes it extra special in the fall season. There are also walking trails and such on the grounds to enjoy.
β Take a drive around Shaftsbury, including Shaftsbury Lake State Park. The back roads around this town have amazing fall color.
β Visit Chiselville and Arlington Covered Bridges, as well as the covered bridges around Bennington.
β Spend some time in Bennington, including the Bennington Battle Monument, the historic district, the Bennington Area Trails System, and the charming downtown. Also, be sure to head to the Apple Barn CafΓ© for cider donuts and amazing baked goods (I love their apple turnovers in the fall!).
β Walk around downtown Manchester, which is broken into two sections: the historic area up by the Equinox Resort, and Manchester Center, which is home to lots more shops and eateries, as well as some outlet stores.
β Visit Shaftsbury Alpacas – get a chance to learn about these beautiful animals while also petting them!
Psst! I have some posts about Vermont that you may find helpful while you plan, including:
- Where To Find The Best Fall Foliage In Vermont
- Best Vermont Pumpkin Patches & Farm Stands
- Awesome Things To Do In Vermont In The Fall
- Coziest Places To Stay In Vermont In The Fall
- My Ultimate Covered Bridges Driving Tour Itinerary
Day 6 – Drive To The Berkshires For One Night
Next up, the beautiful Berkshires!
Much like Vermont, the appeal of The Berkshires is all the rural and countryside scenery, surrounded by the mountains. And since this is probably the best place to experience fall foliage in Massachusetts, itβs a no-brainer to head here next. Plus, the start of The Berkshires is only about an hour from Manchester, VT.
However, if youβve only got 10 days, I do recommend only one night here. There are lots of hotels to choose from, so youβll be able to find a place to stay without a two-night minimum, and while thereβs a lot you can see and enjoy, I think other areas on this list like Vermont and the White Mountains are more worth your time. The Berkshires is also a small region that you can drive around and see a lot with just a day.
Where to stay in The Berkshires: I recommend staying in the southern park, around Lenox and Stockbridge, or even Great Barrington. This will cut down your driving time the next day to Connecticut, and you’ll have time to explore the northern parts of The Berkshires on your drive from Vermont.
Awesome Hotel Options In The Berkshires
These places should allow one-night stays in the fall, too!
π The Lenox Collection: A group of cozy, historic buildings-turned-inns in Lenox.
π Inn at Silver Maple Farm: A homey, farmhouse-style B&B.
π Red Lion Inn: A historic hotel right on Main Street in Stockbridge! It’s a very popular place to stay.
Best Things To Do In The Berkshires In The Fall:
For this part of your trip, I recommend planning your time here from north to south, and make stops along the way from Vermont, and stay somewhere closer to Lenox or Stockbridge. These recommendations are in that order so you can more easily plan:
β Explore the cute college town of Williamstown, where thereβs lots of fall foliage scenery to enjoy. The best way to experience the town is by doing the Field Farm Trail or the Sheep Hill Trail. Both are gorgeous in the fall!
β Drive the auto road to the top of Mt. Greylock. You may just miss peak foliage at the top of the mountain, depending on when you visit, but the views from up here are incredible either way!
β Drive Route 7 down through Pittsfield, and toward Lenox. Stop in Lenox for lots of beautiful fall foliage, and to see The Mount, Edith Whartonβs historic estate, and also walk the trails at the Pleasant Valley Wildlife Sanctuary, if you have the time.
β From Lenox, make a detour to Hilltop Orchards for cider donuts.
β Head to Stockbridge, and walk the small but idyllic Main Street downtown, then visit the Norman Rockwell Museum, and swing by Oliviaβs Overlook for beautiful foliage views.
β Head into downtown Great Barrington, which is still a small town, but more bustling, and has more dining and shopping options.
Day 7 – Drive To The Litchfield Hills In Connecticut For One Night
Welcome to Connecticut! And guys, this is the region that inspired Amy Sherman-Palladinoβs now iconic Stars Hollow town from Gilmore Girls, so you know youβre in for a real treat. Not sure what Iβm talking about? Donβt worry! All Iβm saying is that this area is filled with charming small towns that are extra cozy and beautiful in the fall season.
Where to stay in the Litchfield Hills: So, Iβm not going to sugarcoat it for you, Connecticut is expensive, and the accommodations out this way are not budget-friendly. That said, I have some recommendations for you that allow 1-night stays in the fall season (at least, when Iβve looked for dates in October and booked stays for myself). I also recommend staying close to Litchfield since itβs furthest east. This will just make the most sense with your driving schedule the next day. However, thereβs a good budget(ish) option in the western region, too, and both are totally fine!
Great Hotel Options In The Litchfield Hills:
π Litchfield Inn: This is my personal favorite place to stay when visiting.
π Rocky River Inn: A motel in New Milford that’s one of the most affordable place to stay at in this area.
Best Things To Do & Places To See In The Litchfield Hills In The Fall:
β The best towns to see are New Milford, Kent, and Litchfield, and if you drive to all three in one day, it takes about an hour (plus any time you spend in each place).
β Washington Depot is rumored to be the actual town Amy Sherman-Palladino based Stars Hollow on, however, I actually find it to be the least charming of the towns in this area. However, Po CafΓ© and Hickory Stick Bookshop are worth the excursion over since itβs not far from New Milford!
β In Kent, Kent Falls State Park, Bull’s Covered Bridge, and Main Street downtown are the best places to see with a short amount of time.
β New Milford, the downtown area is so incredibly charming, and I also like to visit Loverβs Leap Bridge.
β Litchfieldβs downtown is also rather idyllic, and a great place to walk around.
β The drives between each destination are really pretty, and you’ll see lots of fall foliage and rural scenery during each portion of your drive around.
β Mount Tom State Park is great for beautiful fall foliage!
β Thorncrest Farm & Milk House Chocolates is a really fun stop to make, especially in the fall for their pumpkin chocolates.
β Averill Farm for cider donuts!
β Hoganβs Cider Mill for Instagram-worthy fall drinks and the most fun fall vibes.
Psst! If you’re a Gilmore Girls fan, you may want to check out my post on Where To Find The Real Stars Hollow π
Day 8 – Drive To Salem, MA For One Night
Optional Adjustment: You can also head straight to Boston for two nights, and just plan Salem as a day trip from Boston, which is very easy with the ferry option.
Heading back into Massachusetts, youβre now on your way to one of the most iconic fall and Halloween destinations in the entire country – Salem. Known for many things, including the Salem Witch Trials, incredible history, and the home to some of the Hocus Pocus movie filming locations, thereβs so much fall fun to have around Salem.
Salemβs fall foliage also peaks later in October, so it;s possible youβll be a bit too early to see it at peak, however, itβs still very much worth a visit.
Salem, while a city, is actually pretty small – or, at least, the area youβll be visiting is. All the top attractions are walkable from one another (for the most part), so you can easily see it all as a day trip, which is why Iβve given you the option to also head straight to Boston, and do Salem as a separate day trip.
Where to stay in Salem: If you choose to stay the night, most places will require a two-night stay, but Iβve found some options that are perfect for a one-night stay. If you’re up for commuting in, you can also look for places in surrounding areas like Peabody and Beverly (which usually have some chain hotels with cheaper rates!).
Hotel Options In Salem Allowing One-Night Stays In October:
π Hawthorne Hotel
π The Hotel Salem
Optional stops in the Sturbridge, MA area on your way:
β Old Sturbridge Village, which is a living museum that replicates life in New England in the early 1800s. There’s lots of beautiful foliage here, a covered bridge, and overall, it’s so fun to walk around. Highly recommend! But this stop does require at least an hour or so. This stop is pretty much on your way to Salem, too!
β Saw Dust Coffee House, which is right by Old Sturbridge Village. This is such a cool coffee shop that always has fun, seasonal drinks, and also delicious baked goods. A great place to stop for a fall drink and snack for the road.
β Tree House Brewing in Charlton, which is just a few minutes from Sturbridge. This is easily the best brewery in New England, so it’s a great stop to make if you love craft beer. They also only sell their beer at their limited locations around New England, not in stores, which is why it’s worth a trip.
Best Things To Do In Salem In October:
β Visit the Salem Witch Trial Memorial. This is a small little memorial by a cemetery, but itβs somehow still very powerful.
β See The House of Seven Gables, which is the actual house that Nathanial Hawthorn wrote about in his book of the same name.
β Walk around the side streets around the House of Seven Gables – lots of beautiful, historic homes are found here!
β Walk past the Witch House. I donβt think itβs necessary to go inside, but itβs one of the last-remaining buildings in Salem with direct ties to the Witch Trials, so you definitely want to at least see the outside.
β Walk over to Chestnut Street, which is regarded as one of the most beautiful streets in the entire country. The houses over here are so stunning!
β Have lunch at the Lobster Shanty, and if youβre up for it, get the lobster martini π
β Walk up and down Essex Street, which is a pedestrian street filled with shops and such.
β Head to the Salem Martime National Historic Park, where youβll find a small lighthouse you can walk to, the Friendship tall ship, and the very cool historic Sail Loft.
β Take a Hocus Pocus tour, which takes you to the filming locations around town! π Click here to check out the tour.
If youβre planning to stay in Boston instead, and taking a day trip to Salem, consider taking the Boston to Salem, MA ferry! Parking in and around Salem in October can be challenging, especially on weekends, and traffic getting in and out of the city can be tough, too. However, the ferry takes away all that potential stress. Driving there and back is still a good option, as the ferry prices can add up quickly, however, the ferry is a very, very convenient and fun options. Be sure to book both your outbound and return tickets, as theyβre reserved in two separate transactions!
π³οΈ Click here to check rates & availability for the Boston β Salem Ferry
Psst! I also have some posts you may find helpful while planning your time in Salem, including my Salem, MA day trip guide, and my guide on the best time to visit Salem, MA.
Day 9 – Drive To Boston, Making Stops On The North Shore (optional)
Depending on your preferences, you can either head back to Boston on this day, or you can drive a bit further north to see some really beautiful foliage towns before heading into Boston. The choice is yours!
About 45 minutes north of Salem is the beautiful town of Newburyport, and itβs a bit of an under-the-radar destination for folks who arenβt local to the area. I always like to describe Newburyport as stepping onto the set of a Hallmark movie. Itβs idyllic, waterfront, and packed with amazing shops and eateries. And, itβs entirely walkable. Every time I take somewhere for the first time, they can’t believe how gorgeous and cozy it is.
Newburyport is also my favorite North Shore town for fall foliage, and youβll find tree-lined streets, and a waterfront park filled with colorful trees toward mid to late October. I absolutely think itβs worth the excursion to explore up this way.
If youβre looking to see some of the North Shore while on your trip, but donβt want to venture all the way up to Newburyport, I also love to visit Manchester-By-The-Sea. This small town is packed with fall color around the same time (toward the end of October), and the waterfront scenery combined with historic buildings is lovely. Itβs much smaller than Newburyport, and offers fewer things to do and see, but it makes for a lovely, quick stop.
Just south of Salem is Marblehead, which is also a very cozy waterfront town to explore in the fall, and less out of the way than both Newburyport and Marblehead. I absolutely love Marblehead, and the historic district is a wonderful place to walk around for an hour or so.
Best Things To Do In Newburyport:
β Walk around Market Square, which is the main downtown area, and visit the shops.
β Walk over to Tannery Marketplace to visit the shops there, and pop into Chococoa for a fall beverage, and one of their delicious homemade whoopie pies.
β Walk along the waterfront, and admire the fall foliage from the park.
β Take a drive over to Plum Island, if you have time, and explore the Parker River National Wildlife Refuge, which is beautiful, and has a lovely boardwalk trail through the salt marshes and along the coast.
Best Things To Do In Manchester By The Sea:
β Park by Masconomo Park, and walk around the harbor. Thereβs tons of amazing foliage here if you can time your visit just right with peak.
β Walk up Beach Street from there, and visit the shops in town.
β In the opposite direction, you can also walk along Beach Street to get to Singing Beach, which is lovely. Itβs named after the sound the sand makes when you cuff your feet in it just right.
Best Things To Do In Marblehead:
β Explore the charming historic area, which is close to the Harbor Light Inn.
β Visit the shops in that same area, mostly along Washington Street.
β Take a drive to Chandler Hovey Park to see the lighthouse.
β Drive over to Castle Hill to take in amazing coastal views. If youβre comfortable with it, you can climb the giant rock, too!
At the end of this day, or late afternoon, head into Boston to spend the night! I have more detailed information on what to see in Boston in the fall in the next section.
Psst! I have some more detailed posts on the best things to do in Newburyport, MA, and the best things to do in Marblehead, MA, if youβre interested in learning more about what they offer π
Day 10 – Explore Boston
The last destination on your New England fall foliage road trip, is Boston. As New Englandβs biggest city, itβs packed with incredible things to do, but honestly, the fall season here is magical. The city is so historic, and filled with cobblestone streets, so the cozy fall season is truly the best backdrop for all of it.
I also saved Boston for last because of all the places mentioned in this itinerary, it’s the last to showcase peak foliage. If you want to see fall color around the city, it typically hits peak closer to the end of October, but you can usually see some fall color by mid-October, depending on the year.
While one night is definitely not enough to experience it all, youβll definitely be able to see the highlights. And if youβre more of a city person, or you want a few nights in one place before flying back home, you can always skip the North Shore/Salem options, and head straight to Boston for a couple of days.
Where to stay in Boston: I always recommend you stay in the downtown area, and ideally, in the Waterfront, Financial, Beacon Hill, Back Bay, or North End neighborhoods. In these areas, youβll be able to walk pretty much anywhere, unless you have mobility concerns.
My hotel recommendations in Boston in the fall:
π Boston Harbor Hotel
π Revere Hotel Boston Common
π The Godfrey
Best Things To Do In Boston In The Fall:
β Walk around the Public Gardens, Charles River Esplanade, and Boston Common. The Gardens and Common are in the heart of the city, and close to each other near Beacon Hill. And the Esplanade is a bit of a further walk, but not bad at all (and totally worth it). These three areas have beautiful fall foliage, and lots of picture-worthy moments.
β Explore the Beacon Hill neighborhood, which is close to the Public Garden. This is my favorite neighborhood in the city, and where youβll find the most charm.
β Grab a fall drink and apple turnover from Tatte (pronounced like latte π). These cafΓ©s are so beautiful on the inside, and there are a few locations around the city.
β Take a spooky tour! There are so many ghost stories and lore that originate in Boston, and these ghost tours are especially fun in the fall season!
β Walk the Freedom Trail. While this isnβt fall-specific, itβs one of the best things to do in the city. This trail winds through a big part of the city, and takes you to the most historically-significant places.
Psst! I have some more detailed guides on Boston you may want to check out, including the best Boston food tours, and visiting Boston in the fall.
12 Day Road Trip Itinerary Option
If you have 12 days (or more!), this is truly awesome. I would follow my 10 day itinerary, and then take one of these suggestions:
Option 1: Add an extra day to either the White Mountains or Litchfield Hills. There’s probably more actual sites to see in the White Mountains, but adding a day to either will allow you a more relaxed pace.
With an extra day in the White Mountains, you may also want to consider taking a drive to the Lake Winnepesaukee area. From the White Mountains, the drive from the eastern side (North Conway, Jackson, etc.), down Routes 113 and 25 are the best option. Some cool stops to check out on this drive are:
β Chocorua Lake and Mountain (the Basin Lot Overlook is great!)
β Sandwich to see Durgin Covered Bridge, Sandwich Creamery, and stop for some bites at The Foothills Cafe & Curio.
β Moultonborough, to visit Castle in the Clouds for awesome views.
β End in the charming town of Meredith on Lake Winnepesaukee, and be sure to drive to Cider Bellies for the best cider donuts I’ve ever had!
Option 2: Use both extra days to head up to Acadia National Park. I used to include this stop in this itinerary, but recently removed it. Why? Most of my readers have an average of 7-10 days for this road trip, and since itβs all about the best foliage, I thought other places around the region offered more in terms of fall color. Acadia is INCREDIBLE, and I recommend going out of your way on pretty much all of my other road trips, especially along the coast. So, this is an awesome option to consider. Thereβs some lovely foliage up in Acadia, but itβs not quite as abundant as places like VT and NH, simply because there are so many pine trees. Is it worth it, though? YES. Especially if you have 12 days or more.
Option 3: Add extra time to Central Vermont to see Burlington, Shelburne, and Lake Willoughby.
Burlington, Shelburne, & Lake Willoughby, VT things to check out:
β First, the drive from both Stowe and Woodstock to Burlington on I-89 is beautiful in the fall. You’ll see lots of mountains ablaze with fall color.
β If you want an especially scenic drive, drive from Stowe or Woodstock to Waitsfield, and cruise along the Appalachian Gap on your way to Burlington/Shelburne. This is a gorgeous drive through the mountains, and there’s an awesome overlook mid-way with an amazing view. This drive is just a bit out of the way, but worth it.
β In Burlington, check out the waterfront area, and walk along Lake Champlain.
β Burlington also has an awesome craft brewery scene, and Foam Brewers is especially great.
β The American Flatbread restaurant in Burlington is a cozy place to stop for lunch.
β Church Street Marketplace in Burlington is a must!
β In Shelburne, you’ll want to spend most of your time walking around Shelburne Farms. This is a historic farm once owned by the Vanderbilt family, and has beautiful hiking trails, and you can also sample their homemade cheeses. Definitely do the Farm Trail, which takes you to an epic view of Lake Champlain.
β Lake Willoughby is a gorgeous lake, and surrounded by mountainous foliage in the fall season. It peaks a bit before the Stowe region, but you may be able to see some epic fall color. Drive around the lake, and hike the Mount Pisgah trail for view of the foliage and lake from above.
More Places To Check Out near Stowe If You Have Time:
Some of these places are further north, and will likely be past peak when you visit, depending on your specific trip timing. However, if you add an extra day to this part of the itinerary, these are some more cool places to check out:
β The covered bridges in Montgomery, including Montgomery covered bridge (which is actually in Waterville), and Longley Covered Bridge.
β Barn Owl Bistro is a hidden gem nearby that’s a great little pitstop.
β The Waitsfield area to see more covered bridges there, and beautiful scenery along the drive.
1 Week (7 Day) New England Fall Road Trip Itinerary
If you have 7 days, welcome to your itinerary!
This option is the same as the 10 day option, with some minor adjustments.
7 Day Road Trip Overview:
Day 1: Arrival In Boston, drive to the White Mountains
Day 2: Explore the White Mountains
Day 3: Drive to Stowe, VT
Day 4: Explore this region of Vermont
Day 5: Drive down to The Berkshires for one night
Day 6: Drive to Litchfield Hills, or Salem, MA
Day 7: Return To Boston for one night
5 Day New England Fall Road Trip Itinerary
With 5 days, you can go in a few different directions, and below, I break down my suggested options, and the benefits of each. This way, you can tailor it to your preferences.
Option 1: Spend two nights in Boston with a day trip to Salem, then spend 3 nights in Stowe/Woodstock, VT.
Option 1 is perfect if you prefer staying in one place longer. This itinerary will allow you to stay in the same hotel in Boston for 2 nights, and take an easy day trip to Salem for the perfect fall day of Halloween fun and history! Then you can pick up your rental car (if you haven’t already), and drive to Stowe or Woodstock, VT for 3 days to explore both towns.
With 3 days in Vermont, you can easily see both Stowe and Woodstock, and maybe even plan a day of driving around the back roads. See the 12-day itinerary option for my suggestions on driving the back roads around Vermont during foliage season.
Option 2: Spend 1 night in Boston, stop in Salem on your way to Franconia and spend 2 nights in Franconia. Then spend 2 nights in Stowe/Woodstock, VT, and then drive back to Boston.
Option 2 is perfect for those who still want to see as much as possible in 5 days. You’ll get to see a bit of New Hampshire and Vermont, while making a stop in Salem.
Note: For this itinerary, I would drive from Salem to Conway, and the drive The Kancamagus Highway on your way to Franconia so you get to experience the fall foliage along this route. But this itinerary option eliminates the stay in Jackson, as there are more fall things to do in Franconia.
Option 3: Spend 1 night in Boston, 1 night in Salem, 3 nights in Stowe/Woodstock, VT, and then back to Boston.
Option 3 is perfect for those who really want to spend some time in Salem. This itinerary allows you to spend a whole night in Salem to really enjoy all the Halloween festivities and tours, and then you can spend 3 beautiful days in Vermont.
I excluded New Hampshire from this option because I felt like it would be too much to cram in when adding 1 night in Salem. But if you were feeling adventurous (I’ve been there, I get it! π), you can drive to Franconia, NH for 1 night after Salem, and then do 2 nights in Vermont instead of 3.
3 Day New England Fall Road Trip Itinerary
3 days in New England is the perfect long weekend getaway!
With 3 days, I suggest you stay in one location, and add day trips. If you’re flying into Boston, you can stay 1 night in Boston if needed, and then drive to Vermont or New Hampshire for 2 nights. If you’re not flying in, you can spend all 3 nights in Vermont or New Hampshire.
Stowe is very close to New Hampshire, and it’s only about 1.5 hours from Franconia. You can easily do a day trip from Stowe to New Hampshire, or vice versa, for this type of itinerary.
It would also be easy to work in a stop in Salem, MA, either on your way in or out of Boston.
Weekend New England Fall Road Trip Itinerary
For a weekend getaway in New England (essentially, 2 days), I would also recommend you stay in one place and take a day trip. For this itinerary, I almost always suggest Stowe or Woodstock. You can stay in either town, and spend 1 day exploring that town, and then the next day, exploring the other as a day trip.
What To Pack For A New England Fall Road Trip
I always start every New England packing guide with the same thing, and this post is no different: begin to check the weather reports 5 days out from your trip to get an idea of what the weather will be like. And keep checking it until the day before you leave.
This is because weather in New England can change quickly, especially in the fall season. It’s not quite as dramatic as say … Iceland π But, it can change and vary a bit. Generally speaking, fall will be chilly and a bit rainy. However, you could also have warm and sunny days. For longer trips, you’ll want to pack for both scenarios.
Here are some things I recommend you consider when packing for a fall road trip through New England:
β Waterproof hiking boots. If you plan to do any hiking, or even nature walks, you’ll want a pair of sturdy boots that are waterproof. Even some attractions like Flume Gorge and other waterfalls in New Hampshire are pretty wet, so this is a good idea to stay dry and comfortable. I really like the Eddie Bauer K-6 Hiking boots. Find the women’s version here and the men’s version here. They’re a much less expensive version of the famous Danner hiking boots featured in the movie Wild π
β Good hiking socks to keep your feet dry. An awesome brand to support is Tarn Tough Socks, which is a Vermont-based company. They’re an investment, but they’re also the best, and come with a lifetime guarantee!
β Waterproof rain jacket to stay dry if it rains. You won’t want to let the rain slow you down, especially if there’s a lot in the forecast! So definitely pack one that’s completely waterproof (not water-resistant).
β Casual Layers. The best way to dress in the fall season is with layers. I usually wear jeans, a light t-shirt, and then a sweater or jacket over that. If it’s forecasted to be chillier than usual, I’ll add a scarf or a hat to keep me warm. New England is a pretty casual place, especially the destinations I’ve listed in this itinerary. No need to pack dresses and such.
β Hiking clothing. For any hikes you want to do, pack whatever clothes you typically wear and feel comfortable in π
β Comfortable walking sneakers or boots. When it’s not raining, a good pair of comfortable sneakers or cute boots work perfectly, depending on your plans. Since I drive from New York, I don’t usually have to worry too much about weight limits on a suitcase, so I’ll throw a pair of sneakers, flat boots/booties, and my hiking boots into the car. This is usually all I ever need.
β Reusable water bottle. You’ll need to stay hydrated while out exploring!
β Day pack. If you plan to do any hiking, you’ll want to bring a day pack with you to carry your essentials. If you don’t plan to do any hikes, you can probably skip this, as you can keep most everything you need in your car or room.
My Tips For Planning A Trip To New England In The Fall
β Book in advance. I can’t stress this enough. Hotels and accommodations book out well in advance for fall foliage season in prime areas, and these prime areas are where you’ll be heading! If possible, begin to book your hotels at least 6 months in advance, but even 8 months is better. For reference, while I began to plan my Vermont fall road trip for the 2023 season, my favorite place to stay in Stowe, VT was fully booked during peak foliage weeks – in FEBRUARY. Yep, February.
β Offline Google Maps! I can’t tell you how important this is! Even as recent as a fall 2023 road trip, I barely had service through much of New Hampshire, Vermont and The Berkshires. I spent a lot of time just driving around hoping my service would come back, or asking people for directions the old-fashioned way. I usually offline maps, but totally forgot that trip, and it was a harsh reminder that this is a must-do.
β Be respectful of private property. Popular places in foliage towns have begun to restrict tourist access to roads because too many people have trespassed to get the perfect photo. Always have an awareness of when you may be encroaching on people’s private homes and land, and follow all signage. Trust me when I say, there are so many places around this entire region that are postcard-worthy, and you don’t need to break any rules to get amazing photos!
β Stay safe while taking photos. Similar to my previous tip, never put yourself or others in danger, to get a great photo. For example, if you see a spot along a road with no safe place to pull over, or the only place to pull over is private property, move on. You’ll drive by so many postcard-worthy scenes, but you can’t snap photos of them all π Allow them to safely live in your memory, and only take the photos that are safe to do so.
β New England’s highways charge tolls. Recently, many parts of this region have switched to electronic tolling, meaning you don’t stop when going through, and your license plate will be billed for the charges. If you’re renting a car, your rental company will go over how this all works, but they will likely just charge your card on file for any tolls you incur during your trip, which is very easy!
β Lastly, prepare to pay. Yes, the sad truth is that peak foliage season in New England is expensive, and it won’t be your most budget-friendly trip ever. There are ways to keep costs down, and I’ll go more into that later in the post as well, but generally speaking, this is an expensive time to visit New England – at least, where the foliage is the best π
How Do To A New England Fall Trip On A Budget
So, first thing’s first, you’ll unfortunately have to rethink what “budget” means in New England, especially during peak season in the fall. It’s generally more expensive than other areas of the country regardless of the reason, so during prime foliage times, prices will go up significantly.
Especially in the past, I never had the money to spend on several nights at hotels during this time of the year, so I have learned to do it on more of a budget. Not necessarily cheap, but not as tough on the wallet π Here are my tips:
β Stay in motels. I love a good hotel splurge, and do it more now than I did in my 20s and early 30s. But for most of my road trips when the focus is exploring outdoors, I stay in motels with efficiency kitchens. You can find some really nice ones, and while they’re likely to be outdated, they’re usually clean and cozy.
β Efficiency kitchens allow you to make some meals at home. For a road trip style trip, this may be more challenging, as it’s hard to bring perishable items with you to store in a fridge. But I usually try to make my own breakfasts to save money, and pack snacks to have for lunch.
β Stay outside of town. If you’re really on a tight budget, you can stay outside of the towns you’re visiting. Places like Franconia, Stowe, and Woodstock charge premium rates for peak season, so you’re likely to find deals a town or two away.
β Go camping! If you’re really adventurous, you can go camping! There are camp sites all over New England, and this will definitely be more affordable. One thing to keep in mind is the colder weather, and for this reason, some camp sites may close down after Indigenous People’s weekend in October. But many remain open, and offer Yurt-style camping, too.
New England Fall Road Trip – FAQ
Does It Snow In New England In The Fall?
Here’s the thing – it might if you’re up in the mountains. However, it doesn’t usually snow during peak foliage times. Usually, New England gets its first snow of the year later in October or early November. So, I wouldn’t worry about packing any snow gear or winter boots for your fall road trip. If it does snow, it likely won’t be a lot.
Are The Fall Colors As Bright In Person As They Are In Photos?
Most of the time, yes, which is why it’s so amazing to see it in person. I know that some photographers like to amp up color saturation when they edit their photos, and for any that take it too far, you can usually tell because it looks borderline fake. But many of the photos you see online and on social media are accurate. When I edit my fall photos, I’m really careful to edit the color saturation to accurately reflect what I experienced in person.
It’s good to know that color intensity with fall foliage can vary each year, though, and is impacted by weather conditions leading up to peak foliage times. For example, if there’s not enough rain prior to peak foliage, the colors may not be quite as bright, and display in more muted rust tones. However, often the colors are truly vibrant oranges, reds, and yellows.
Is Fall In New England Worth It?
A resounding yes! I truly believe this is such a magical time to visit – if not the most magical time. Despite the crowds and the cost, it’s more than worth it. Many of the landscapes you’ll see are actual stock photos and postcards, and since so many people equate the fall season to all things cozy, there’s really no cozier place to be than in New England during foliage season.
More posts you may enjoy:
- Fall In New England: The Best Things To See & Do
- Fall In New Hampshire: The Best Things To Do
- Fall In Massachusetts Ultimate Guide: All The Best Things To Do & Foliage Spots!
- The Best 7 Day New England Road Trip Itinerary For Any Season
- Best Stops To Make On A Boston To Stowe, VT Road Trip
- Vermont Vs. New Hampshire In The Fall
- Maine In October: Best Towns For Foliage & Things To Do!
- Best Time To Visit New England
- Best Time To Visit Vermont
That’s A Wrap On The Best New England Fall Road Trip Itinerary
And there you have it! All my tips and expert advice on planning the most epic New England fall road trip during foliage season! This truly is such a wonderful, once-in-a-lifetime experience that everyone should do at least once, and hopefully, you’re now well on your way to planning your own foliage adventure through New England!