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 😉
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 😉), 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.
This particular itinerary will cover 10 days, and offer suggestions on how to make the trip shorter as well.
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, this itinerary will take you to Massachusetts, New Hampshire, Vermont, and Connecticut. 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.
I 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:
→ It begins in Boston. Most of my road trips begin and end in Boston because it’s the biggest airport with the best and most affordable flight options, and it’s also a centrally-located destination to start a road trip. 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.
→ 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!
→ 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!
→ I give you options! Of course, I stand by all my suggestions 😉 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 more of Vermont (I have great suggestions for you!)
Day 5: Drive to southern Vermont, and spend one night around the Manchester area
Day 6: Drive through The Berkshires to Connecticut, spend two nights in Connecticut.
Day 7: Explore the Litchfield Hills region of Connecticut.
Day 8: Drive to Salem, MA to explore for a few hours (optional), and then head to Boston.
Day 9: Explore Boston.
Day 10: Travel day home (with options of things to do if you have time during the day).
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 😉 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:
🍁 Sugar Hill Inn – 15 mins from Franconia Notch Park, and is rated as the best B&B in New Hampshire!
🍁 Riverwalk Resort – 5-7 mins from the top attractions in Franconia.
🍁 Woodstock Inn & Brewery – Cozy inn with a brewery.
Best Things To Do In The White Mountains In The Fall:
→ 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!
→ 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.
→ 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.
→ 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.
→ 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 😉).
→ Drive through Crawford Notch State Park to be rewarded with more stunning views of the mountains ablaze with foliage color!
→ 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!
→ 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!
→ Hike the Arethusa Falls Frankenstein Cliffs Trail in Crawford Notch State Park. This trail also has a detour for the epic railroad-through-the mountains overlooks (pictured below)!
→ 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:
✓ 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.
✓ 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.
✓ 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.
✓ 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.
✓ 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?
🍁 Consider downloading this Kancamagus Highway 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 you’ve been hoping for. I also love Vermont because it has more of a New England vibe than the White Mountains, so you’ll 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 they’re only about 1.5 from one another. Both are charming towns, and you can’t go wrong with either.
If you need more detailed information on deciding where to stay, I have an entire post on Stowe Or Woodstock, VT: Which Is Better To Stay In, which you should find helpful!
Where To Stay In Stowe:
🍁 The Green Mountain Inn. It’s located right on Main Street, so you can walk to a lot of places.
🍁 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:
🍁 506 Inn On The River. Located just outside of the village, this is a modern and cozy inn, well … right on the river
🍁 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, they’re so worth it! I’ve listed them down below for you:
→ Peachum, VT, which is a very small, rural community, but the foliage views around here are like literal postcards.
→ Danville to do the Great Vermont Corn Maze, which is the largest in New England. It’s so big that you’ll need a couple of hours here, but it’s a very fun experience. Keep in mind that it’s only open until mid-October – be sure to check their website or Facebook page for updated info.
→ 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 – it’s even better in the fall season!
→ Bogie Farm in East Ryegate is a landscape that’s 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 😊
Best Things To Do In Stowe, VT In The Fall:
→ Drive Smugglers Notch, which is a short but scenic drive through mountains, and offers incredible opportunities to see fall color.
→ 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.
→ Explore the charming downtown along Main Street, which has great shops, cafés, foliage views, and access to the Recreation Path.
→ 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, you’ll cross pretty bridges (one of which is the Brookdale Covered Bridge!), and enjoy some more peaceful moments.
→ Visit Gold Brook Covered Bridge, which is also known as Emily’s Bridge. This bridge is said to be haunted, so it’s the perfect spooky season photo opp! Please just practice caution and respect while visiting, as it’s a bridge that’s still used by the locals – definitely don’t block traffic by standing in the middle of the road!
→ Take a drive to Waterbury, which is home to Cold Hollow Cider Mill, Ben & Jerry’s, and the Cabot Cheese Farmer’s 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!
→ Visit Stowe Cider, which is just perfect during the fall season.
Best Things To Do In Woodstock, VT In The Fall:
→ Walk around the charming village, which is lined with fall foliage trees, and awesome fall decorations.
→ Snap a photo with Middle Covered Bridge, which is located right in the village.
→ 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.
→ Visiting Billings Farm & Museum, which is a working dairy farm and museum, and is such a wonderful place to experience.
→ Visit the town’s other two covered bridges: Taftsville and Lincoln.
→ 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.
→ Get a maple creemee around the village – this is Vermont’s version of soft serve ice cream, but it’s 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 you’ve explored Central Vermont, it’s 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 it’s 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 you’ll have an easier time finding places to stay that don’t 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, you’ll 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:
🍁 Hill Farm Inn: Absolutely incredible property in the countryside, with on-site dining in a barn, cozy rooms, and mountain views from their porch.
🍁 Kimpton Taconic: Beautiful rooms and a boutique-style hotel, located in Manchester.
🍁 Four Chimneys: One of the best inns in Southern Vermont, located in Bennington.
Notable stops to make on the way to Southern Vermont:
→ I suggest taking the Route 100 option, which only adds a few minutes to the drive.
→ 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.
→ 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.
→ 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:
→ 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 it’s such a fun experience. There is a fee to drive this road, so plan accordingly.
→ 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.
→ Take a drive around Shaftsbury, including Shaftsbury Lake State Park. The back roads around this town have amazing fall color.
→ Visit Chiselville and Arlington Covered Bridges, as well as the covered bridges around Bennington.
→ 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 Café for cider donuts and amazing baked goods (I love their apple turnovers in the fall!).
→ 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.
→ 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 Through The Berkshires On Your Way To Connecticut
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, it’s a no-brainer to head here next. Plus, the start of The Berkshires is only about an hour from Manchester, VT.
The reason I recommend just driving through instead of spending a night here is because The Berkshires is a region that’s harder to find 1-nigh stays during fall foliage season, and there are also fewer attractions and things to do. I also 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, and it’s absolutely beautiful. But you can definitely see the highlights in a day.
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:
→ Explore the cute college town of Williamstown, where there’s 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!
→ 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!
→ Drive Route 7 down through Pittsfield, and toward Lenox. Stop in Lenox for lots of beautiful fall foliage, and to see The Mount, Edith Wharton’s historic estate, and also walk the trails at the Pleasant Valley Wildlife Sanctuary, if you have the time.
→ From Lenox, make a detour to Hilltop Orchards for cider donuts.
→ Head to Stockbridge, and walk the small but idyllic Main Street downtown, then visit the Norman Rockwell Museum, and swing by Olivia’s Overlook for beautiful foliage views.
→ Sheffield Covered Bridge, which is a really beautiful bridge in the southern region of The Berkshire that’s just a short detour off the road.
End your day in Litchfield, CT, and I really recommend that you stay in Litchfield at the Litchfield Inn. Surprisingly, there are not many hotel options in this region, considering all the wonderful things to do, and many of them are incredible expensive. The Litchfield Inn strikes a great balance between having a cozy inn feel that’s really nice, without falling into a luxury pricing category.
Great Hotel Options In The Litchfield Hills:
🍁 Litchfield Inn: This is my personal favorite place to stay when visiting.
🍁 Rocky River Inn: A motel in New Milford that’s one of the most affordable place to stay at in this area, and this is also an option if the Litchfield Inn is booked, or out of your budget.
Day 7 – Explore The Litchfield Hills Of Connecticut
Welcome to Connecticut! And guys, this is the region that inspired Amy Sherman-Palladino’s now iconic Stars Hollow town from Gilmore Girls, so you know you’re in for a real treat. Not sure what I’m talking about? Don’t worry! All I’m saying is that this area is filled with charming small towns that are extra cozy and beautiful in the fall season.
Best Things To Do & Places To See In The Litchfield Hills In The Fall:
→ The best towns to see are New Milford, Kent, Washington Depot, and Litchfield, and if you drive to all of them in one day, it takes a little over an hour (plus any time you spend in each place).
→ Washington Depot is rumored to be the actual town Amy Sherman-Palladino based Stars Hollow on. There are a few cute cafés to check out, the Hickory Stock Book Shop, the lovely Five Janes boutique, and the trails at Hidden Valley Preserve, which is also home to the Henry David Thoreau Suspension Bridge.
→ 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.
→ New Milford, the downtown area is so incredibly charming, and I also like to visit Lover’s Leap State Park in the fall.
→ Litchfield’s downtown is also rather idyllic, and a great place to walk around. However, there’s not a to to do in the downtown area, but Litchfield has the wonderful White Memorial Conservation Center trails, Topsmead State Park, and so many more things to check out.
→ 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.
→ Mount Tom State Park is great for beautiful fall foliage and a fun tower hike with awesome views.
→ Thorncrest Farm & Milk House Chocolates is a really fun stop to make, especially in the fall for their pumpkin chocolates.
→ Averill Farm for cider donuts!
→ Hogan’s Cider Mill for Instagram-worthy fall drinks and the most fun fall vibes.
Psst! I have a few guides on the Litchfield Hills region, if you need more help with this part of your trip:
- Where To Find The Real Stars Hollow, if you’re a fan of the show 😉
- Best Things To Do In Litchfield, CT
- Best Things To Do In New Milford, CT
- Best Things To Do In Simsbury, CT
- Best Things To Do In Kent, CT
- Fall In Connecticut Guide
Day 8 – Drive To Salem, MA For The Afternoon, End In Boston
Heading back into Massachusetts, you’re 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, there’s so much fall fun to have around Salem.
Salem’s fall foliage also peaks later in October, so it’s possible you’ll be a bit too early to see it at peak, however, it’s still very much worth a visit.
Salem, while a city, is actually pretty small – or, at least, the area you’ll 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 I’ve given you the option to also head straight to Boston, and do Salem as a separate day trip.
This is an optional stop if you’ve always wanted to experience Salem in October. However, you can, of course, just head straight to Boston for a more relaxed day. Can’t decide? I have an entire post on the best time to visit Salem, MA, which has a section on visiting in October – that may help you decide!
Optional stops in the Sturbridge, MA area on your way:
→ 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!
→ 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.
→ 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:
→ Visit the Salem Witch Trial Memorial. This is a small little memorial by a cemetery, but it’s somehow still very powerful.
→ See The House of Seven Gables, which is the actual house that Nathanial Hawthorn wrote about in his book of the same name.
→ Walk around the side streets around the House of Seven Gables – lots of beautiful, historic homes are found here.
→ Walk past the Witch House. I don’t think it’s necessary to go inside, but it’s 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.
→ 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.
→ Have lunch at the Lobster Shanty, and if you’re up for it, get the lobster martini 😉
→ Walk up and down Essex Street, which is a pedestrian street filled with shops and such.
→ Head to the Salem Martime National Historic Park, where you’ll find a small lighthouse you can walk to, the Friendship tall ship, and the very cool historic Sail Loft.
→ Take a Hocus Pocus tour, which takes you to the filming locations around town! 🍁 Click here to check out the tour.
Psst! I also have a post on taking a Salem, MA day trip, which you may find helpful while planning your time there.
End your day in Boston! After exploring Salem for a few hours, you’ll want to head to Boston. My advice is to return your rental car at the airport, and then take public transportation into the city via Uber, Lyft, the T (Boston’s subway), or the ferry.
Day 9 – Explore Boston
The last destination on your New England fall foliage road trip is Boston. As New England’s biggest city, it’s 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 day is definitely not enough to experience it all, you’ll definitely be able to see the highlights.
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, you’ll be able to walk pretty much anywhere, unless you have mobility concerns.
My hotel recommendations in Boston in the fall:
🍁 Boston Harbor Hotel
🍁 Revere Hotel Boston Common
🍁 The Godfrey
Best Things To Do In Boston In The Fall:
→ 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.
→ Explore the Beacon Hill neighborhood, which is close to the Public Garden. This is my favorite neighborhood in the city, and where you’ll find the most charm.
→ Grab a fall drink and apple turnover from Tatte (pronounced like latte 😉). These cafés are so beautiful on the inside, and there are a few locations around the city.
→ 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!
→ Walk the Freedom Trail. While this isn’t fall-specific, it’s 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.
Day 10: Travel Day Home
This is your day to travel back home. However, if you have some extra time before you have to leave, you can have your hotel hold your bags for you after check out, and explore of the city. Here are some bonus suggestions for you:
→ Visit the Isabella Stewart Gardner Museum, which is designed like a Venetian palace, and one of the most unique art museums in New England.
→ Snap some photos at the Fan Pier Park harbor front area in Seaport, which has an awesome view of the city skyline.
→ Do some shopping on Newbury Street or the Prudential Center.
→ Visit the Boston Tea Party & Ships Museum, as well as Abigail’s Tea Room, where you can taste the five types of teas that were famously tossed overboard during the Boston Tea Party.
Have 7 Days For Your Road Trip?
If you have a week for your New England fall foliage vacation, I’d recommend focusing your time on the White Mountains in New Hampshire, and then Vermont, as this is where you’ll be able to maximize your time the most. This will also allow you to stay two nights in each destination, and avoid 1-night stays, which are very difficult to come by at hotels during peak foliage season.
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 😉 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:
→ 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 😉
→ 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!
→ 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).
→ 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.
→ Hiking clothing. For any hikes you want to do, pack whatever clothes you typically wear and feel comfortable in 🙂
→ 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.
→ Reusable water bottle. You’ll need to stay hydrated while out exploring!
→ 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
→ 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.
→ 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.
→ 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!
→ 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 😉 Allow them to safely live in your memory, and only take the photos that are safe to do so.
→ 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.
→ 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 😉
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 😉 Here are my tips:
→ 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.
→ 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.
→ 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.
→ 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!
