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 10 years, and have done so many fall foliage road trips. It took me a while, but I’ve finally put together the perfect itinerary for you based on real experience!
This post details where the best places are, the best times to plan your road trip, 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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Tips For Planning A Trip To New England In The Fall
There are some important things to know before you begin to plan your perfect New England fall road trip, so let’s get that out of the way first 😉
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-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.
I go into peak foliage times in each region in a bit, so definitely be sure to read that through, too!
Another important thing to know is that you should anticipate all kinds of weather. I’ve done many fall road trips through this region, and have had warm, sunny days, and trips where it rained almost every single day. I’ll go more into what to pack for this trip at the end of the post to help you prepare, but this is a good thing to be aware of.
Also, 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 2022 road trip, I barely had service through much of New Hampshire and Vermont. 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.
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 😉
What Is The Best Time To Visit New England For Fall Color?
In a nutshell, the last week of September, or the first week of October.
However, it does vary depending on where you’re heading.
As mentioned before, the colors will begin to change in the northern regions first, and then the southern regions will follow later. Most people will choose to visit Maine, New Hampshire and Vermont during their New England fall road trip (and spoiler alert: this is also where I’ll be suggesting you go!), so this timeframe works very well for these areas.
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.
Massachusetts often peaks right around Indigenous People’s weekend as well, with southern MA peaking a week or so later.
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 12 day 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.
If you’re local to New England, and don’t have 10 days, 7 days is again a nice sweet spot. 5 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 are 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 spots, I recommend sticking to Maine, Massachusetts, New Hampshire and Vermont. And flying into Boston.
Why?
Because these areas offer the most spectacular displays of foliage, most picturesque scenery, tons of things to do, and they’re all reasonable close to one another, allowing you to maximize your time.
Here’s why I don’t necessarily recommend states like Connecticut or Rhode Island if you have less than 10 days – they’re further away from the best places to see in the fall.
I truly love every single New England state, and I do really enjoy Connecticut in the fall. However, it’s so far west that you’ll spend more time driving to get there, and possibly forgoing some really spectacular places in Maine, New Hampshire, Massachusetts, and Vermont.
If you have 10 days or more for a New England fall road trip, then I would highly suggest you consider adding in the Litchfield Hills regions of Connecticut, which you’ll see I included in my itinerary. It’s also very close to The Berkshires region, so you can combine it with that part of the trip, depending on how much time you have. However, with less than 10 days, I personally don’t feel like it’s worth it. Especially for first-timers.
If you’ve already seen some of the places I’m recommending in this post, then definitely try to swing over to Connecticut and experience a new area during the fall!
If you have less than 10 days, you may even want to focus all your time on Vermont and New Hampshire. The reason for this is because some of the best places for fall foliage in Maine are further north. I think places like Acadia National Park are very worth seeing (and you’ll see I’ve incorporated it into some of my itineraries!). However, if you prefer a slower pace and less driving, Vermont and New Hampshire are the absolute best places to see.
Some Things To Know About My Itineraries
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.
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 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
Day 2: Explore Boston Or Take A Day Trip To Salem
Day 3-4: Bar Harbor/Acadia National Park + An Optional Stop In Salem
Day 5: Jackson, NH
Day 6: Franconia, NH (Driving The Famous Kancamagus Highway To Get There!)
Days 7-8: Stowe & Woodstock, VT
Day 9: The Berkshires and/or Litchfield, CT
Day 10: Back To Boston + A Stop In Sturbridge, MA or Litchfield, CT
Breakdown Of The 10 Day Itinerary Option
Day 1: Arrival In Boston
Take this time to arrive, get settled, and maybe take in a few sites around the city! Have some time on your first night here? Jump down to Day 2 for some suggestions on what to do!
Where To Stay In Boston:
- Luxury: The Langham
- Splurge: Boston Harbor Hotel
- Moderate: Revere Boston Common
Pro Tip On Fall Foliage In Boston: Foliage peaks later than the rest of the places listed in this itinerary – usually mid-late October. So while you probably won’t see peak foliage in Boston if you plan your trip for peak foliage in Vermont, New Hampshire and Maine, it may catch a glimpse of it on your back if you’re planning a longer trip! Or, you can leave the airport to immediately begin your drive to Maine, and plan to stay a night or two in Boston before you have to fly out.
Day 2: Explore Boston
Boston during the fall season has so much to see and do, but here are some highlights to consider if it’s your first visit:
- Public Gardens (very scenic garden area with a beautiful pond and pedestrian bridge (also makes for lovely photos!). This is a good spot for fall foliage in the city, too.
- Newbury Street for shopping
- The North End for history and food
- Beacon Hill for charming cobblestoned streets at the famous Acorn Street
- Take a food tour if it works with your schedule. There’s incredible food to be had in Boston, and taking a tour with a local expert is a great way to sample lots of delicious things in a short amount of time!
Click here to check out my post on the best Boston food tours!
Day 2: Optional Day Trip To Salem
If you would prefer to take a day trip to Salem, rather than stopping on your way to Acadia National Park, this is a great option! And really, there’s no right or wrong choice here – it just comes down to which you prefer.
Salem is an easy day trip from Boston without a car because of this convenient ferry!
Click here to check out the Boston → Salem Ferry!
Click here for my guide on taking a day trip to Salem!
Day 3: Drive To Bar Harbor & Acadia National Park
Acadia National Park is one of the best things to do in New England year-round, so this is definitely a must if you’ve never been. It also offers some really wonderful foliage, and fall is my personal favorite season to visit for this reason.
This drive from Boston to Bar Harbor takes about 5 hours without stops, which is why I usually suggest you make a pitstop to break up your journey. I actually have some posts on stops you can make along the drive, so be sure to check those out below.
But since Salem is really the ultimate fall destination in Massachusetts, I suggest you pick that as a stop on the drive 🙂
Bar Harbor is the town adjacent to Acadia National Park, and where most people will choose to stay when visiting. Once you arrive, take some time to get settled, and then head out into downtown Bar Harbor to explore this charming seaside town, visit the shops, and grab a great dinner!
Where To Stay In Bar Harbor:
- Bayview Hotel. An oceanfront boutique hotel with awesome views. Perfect for a splurge on your trip!
- Bar Harbor Villager Motel. Clean, updated and spacious. Also, walkable to everything in town.
- Little Fig Hotel. A cute, modern boutique hotel walkable to town.
Here are some posts that will help you further plan this portion of your trip:
- Best Stops To Make Driving Boston To Portland, Maine
- Best Stops To Make Driving Portland to Acadia National Park
- The Perfect Acadia National Park Itinerary (read this one for more information on Bar Harbor and things to do!)
Day 4: Explore Acadia National Park
Even in just 1 day, you can visit some of the best places in the park, and also some really wonderful fall foliage spots. Here how I suggest you plan your day:
If you’re up for it, starting your day with sunrise at the top of Cadillac Mountain is always incredible! This will be great for fall foliage, too. You can also choose to do this the following morning before leaving.
Next, head to the Jesup Path scenic walk, which is especially beautiful in the fall season.
Then, park at the Sand Beach parking lot, and walk the Ocean Path for incredible views. This is 1-mile each way, but offers some of the most iconic views in the park, including the Otter Cliffs and Thunder Hole. It’s also flat and easy, making it very relaxing. Have your camera ready for this one!
For a more advanced hike with awesome foliage views, you can do the Beehive Trail from Sand Beach lot, too.
Continue on Park Loop Road to Jordan Pond House for lunch, and enjoy the views of the pond and mountains. You can also choose to walk around the pond if you have time after lunch.
For more foliage views, hike the Bubble Rock Trail after lunch.
Day 5: Drive To Jackson, NH + Spend The Night
Without stops, this drive takes about 4 hours and 15 minutes.
One stop I suggest making on the way if you enjoy local craft beer is the Oxbow Beer Garden in Oxford, ME. It’s got a very cool outdoor setting, and they have fantastic craft beer.
I recommend spending the night in Jackson because it’s a longer drive from Bar Harbor, and there are some fun things to do in the area. Also, there’s a very scenic drive called The Kancamagus Highway that’s stunning in the fall season with foliage, and I want to make sure you have time to drive it. But more on that in Day 6 🙂
Here are some fun fall things to check out in Jackson:
- The Cog: This mountain railroad takes you to the summit of Mount Washington, the tallest peak in New England! It’s about 45 minutes from Jackson, but you’ll drive through Crawford Notch State Park, which is very scenic, and The Cog is simply incredible in the fall season. If you leave Bar Harbor early enough and have time to do this, I highly recommend it!
- Honeymoon Covered Bridge & Flossie’s General Store
- Glen Ellis Falls
- The cute town of North Conway
Where To Stay In Jackson:
- Christmas Farm Inn (this place is super cozy!)
- The Inn At Thorn Hill & Spa
Option To Stay In North Conway: North Conway is only about 12-15 minutes from Jackson, so you can really stay in either. I think Jackson has better hotel options, and it’s a bit closer to The Cog, which is why I suggested you stay there. But either town works for your New England fall road trip!
Here are some fun things to check out in North Conway if you choose to visit:
- Cathedral Ledge Distillery
- Ledge Brewing Company (between North Conway and Jackson, technically)
- The cute downtown area and Zeb’s General Store (one of my all-time favorite general stores!)
- North Conway Scenic Railroad
Day 6 – Drive The Kancamagus Highway To Franconia, NH
The Kancamagus Highway (Route 112) is a scenic drive that’s regarded as one of the best drives for fall foliage, so this is something you’ll definitely want to do on your New England fall road trip. It connects the towns of Woodstock and Conway, so you can easily start this drive just a few minutes from Jackson or North Conway.
For this day, I suggest you get up early to make sure you have time to explore Franconia Notch State Park after driving The Kanc.
Tips For Driving The Kanc:
- Remember earlier in the post when I said you’ll lose cell service in much of New Hampshire and Vermont? Well, this is one of those drives where there’s no service, so offline your maps before starting!
- There are no bathrooms or gas stations on the drive, so plan accordingly.
- The Kanc takes about 45 minutes one-way without stops, but you’ll want to budget about 2 hours to make some stops at the overlooks.
- During the fall season, especially on weekends, it’s possible traffic could slow down as people try to pull in and out of the parking areas. Plan for some slower traffic.
Pro Tip: Before hopping onto The Kanc, there’s a great little place called Cheese Louise just before the entrance to The Kanc, and this is an awesome place to grab some food before the drive! Especially on a chilly, fall day, a grilled cheese sandwich totally hits the spot, right? 😍
Stops To Make On The Kanc (in order from Conway to Woodstock):
- Albany Covered Bridge
- Rocky Gorge Scenic Area (parking can be found at 44.0016667175862, -71.27716637107925)
- Sabbaday Falls
- Sugar Hill Scenic Overlook
- CL Graham Wangan Overlook
- Hancock Overlook (this one is right at the famous hairpin turn – can’t miss it!)
- Lincoln Woods Trailhead – Scenic suspension bridge over the river that’s not far from the parking lot.
🍁 Before hopping on The Kanc, consider downloading this great audio tour to enhance your drive –
Click here to check out this audio tour!
There are also tons of hiking trails along The Kanc, so if you’re looking to squeeze in a hike on the drive, this is something to consider. But if you don’t have extra time, I would suggest moving on to Franconia Notch State Park, and only doing hikes along The Kanc if you’re able to add an extra day in.
After The Kanc, your next stop is Franconia Notch State Park. And this is where most of the top things to do are, especially in the fall season.
Flume Gorge is one thing I recommend you do if you can only pick one attraction. Flume Gorge is a very fun 2-mile loop trail that takes you over 2 covered bridges, and through the granite gorge. Along the trail, you’ll have some really gorgeous spots to admire the fall foliage, too.
Pro Tip: Buy your Flume Gorge ticket online in advance to save a few bucks! On weekends in the fall season, it’s also possible that certain time slots will sell out. This is another reason to book in advance.
If you have time to explore more of Franconia Notch State Park, I also recommend these activities:
- Cannon Mountain Aerial Tramway
- Artist Bluff Trail (famous spot that ends overlooking Echo Lake – amazing during foliage season!)
- The views at Echo Lake Beach
Where To Stay Near Franconia:
- 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.
Here are some posts to help you plan this portion of your trip:
Day 7 – Drive To Stowe Or Woodstock, VT
Begin your day in New Hampshire with a country breakfast at Polly’s Pancake Parlor! This place is famous in New England, and truly has some of the most amazing pancakes I’ve ever had. It does get busy in the fall season, but man, it’s so worth it.
Then, on to Vermont you go! For the next 2 nights, you’ll want to choose between Stowe and Woodstock, VT as your home base. These towns are the absolute best to visit in Vermont during a New England fall road trip because of foliage views and small-town charm. They’re only 1 hour and 15 minutes from each other, so, you can choose where you want to stay, and then visit the other as a day trip.
The drive to both Stowe and Woodstock is 1 hour and 30 minutes from Franconia, and since this is a shorter drive, you can make some stops along the way, or drive straight there. Stowe and Woodstock both have a lot to do, even though they’re small towns, so it’s beneficial to drive straight there and make sure you have plenty of time to explore.
If you choose to stay in Woodstock, I suggest stopping at the King Arthur Baking Company campus on your way because it’s pretty much on the direct route. It’s a really fun place with fresh baked goods and breads, a café, and a fun shop where you can stock up on pantry staples and baking mixes.
Do I recommend you stay in Stowe or Woodstock? I honestly love both equally! There’s no wrong choice here.
The biggest difference between the two is that Woodstock feels a bit more upscale, and Stowe definitely has a very casual feel to it. But the difference is minor. Both have charming covered bridges, great shops, amazing restaurants, a quaint town feel, and plenty of things to do.
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:
- 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!
- 506 Inn On The River. Located just outside of the village, this is a modern and cozy inn, well … right on the river 😉
Here are some posts that will help you plan your time in Stowe and Woodstock:
Day 8 – Explore Stowe & Woodstock, VT
Depending on where you stay, you’ll want to take a day trip to the other town this day. Below are breakdowns of the can’t miss things to do in each town.
Best Things To Do In Stowe:
- Explore the cute shops along Main Street (don’t skip the Stowe Mercantile!)
- Drive Smugglers Notch for amazing foliage.
- Ride the gondola to the top of Mount Mansfield, the highest peak in Vermont (this is epic during the fall season!). This is located at the midway point along the Smugglers Notch drive.
- Visit Emily’s Covered Bridge, and learn about it’s spooky history.
- Sample the hard cider at Stowe Cider.
- Sip on craft brews at Alchemist Brewing (one of my favorites in New England).
Best Things To Do In Woodstock:
- Stroll through the charming downtown shops and eateries.
- Pop into Mon Vert Café for a warm drink.
- Snap a photo with Middle Covered Bridge in town.
- Drive over Taftsville Covered Bridge to visit Sugarbush Farms. You’ll be able to sample homemade cheese and fresh maple syrup here, and also take in amazing foliage views.
- Visit Billings Farm & Museum.
- Drive over to Sleepy Hollow Farm to see the famous farm landscape spot.
Day 9 – Drive To The Berkshires Or Litchfield, CT
Next up – The Berkshires or Connecticut! This choice is yours entirely. Let’s start with the option to drive to The Berkshires.
The Berkshires is an iconic region in Massachusetts that’s a really great one to visit for fall foliage. Here, you’ll find cute towns, loads of fall color, lots of scenic hikes and walks, and awesome dining options.
Depending on which town in Vermont you’re coming from, the northern region of The Berkshires area will be just over 2 hours from Woodstock, or just over 3 hours from Stowe.
The drive from either town to The Berkshires will pass through Rockingham, VT, and you’ll definitely want to stop here to visit the Vermont Country Store! There’s also the very cute Kissing Covered Bridge here that makes for a fun photo.
Once you arrive in The Berkshires, I suggest you start in Williamstown, and drive the scenic Route 7 down to Sheffield. This drive without stops takes about 1 hour and 15 minutes, but I would budget at least a few hours to make stops and enjoy some other fun activities. This route packs a lot into a perfect fall day, without a lot of driving.
During this drive, these are the best stops to make:
- The Mount Greylock Auto Road to the highest peak in Massachusetts (absolutely amazing in the fall season!).
- Make a detour off Route 7 to Bartlett’s Orchard in Richmond for the perfect fall farm experience.
- Continue with your short detour to Hilltop Orchards, which is 5 minutes from Bartlett’s, and where you can sip on artisanal craft ciders!
- Walk through the charming town of Lenox.
- Stroll through quaint Stockbridge, too!
- Snap photos with the covered bridge in Sheffield.
Where To Stay In The Berkshires:
- The Red Lion Inn. A historic and famous inn in the heart of Stockbridge.
- The Dewey. A cozy, traditional New England B&B in Lenox.
The other option is to drive to Litchfield, CT, which is south of The Berkshires. It’s a longer drive from Vermont, but you could also turn this into a fun road trip day by driving the same Route 7 itinerary as mentioned above through The Berkshires, and then continue on to the Litchfield Hills. I would probably only choose this option if you wanted to take your time exploring the awesome stops along Route 7 in The Berkshires, arrive in CT in the evening, and then explore this region of CT the next morning before your drive back to Boston.
How To Spend Your Time In Litchfield Hill, CT:
Since you’re likely coming down through the western border of Massachusetts, I would start in Kent, and work your way east. You probably won’t have time to do everything on this list, but pick and choose based on your preferences and schedule.
- Explore the cute town of Kent, and then visit Kent Falls State Park if you have time.
- Continue to follow Route 7 to New Milford. The drive is very scenic!
- Stop in New Milford to enjoy the quaint town, and then visit Lover’s Leap Bridge.
- Head over to Washington, and then continue on to Mount Tom State Park for awesome foliage.
- End in the charming town of Litchfield.
Where To Stay In The Litchfield Hills: Litchfield Inn. Refined and still very cozy, and one of the best in the area!
Should I do The Berkshires or Litchfield, CT? Personally, I would stay stick to The Berkshires since this will allow you a more relaxed itinerary. There’s so much to do, and plenty of foliage scenery to take in. If you do the Route 7 drive quicker than you were anticipating, you could always shoot down to the Litchfield Hills for an impromptu adventure 🙂
I would choose to add on the Litchfield Hills if you’re feeling adventurous, and really want to see as much of New England as possible.
Day 10 – Drive Back To Boston, Stopping In Sturbridge or Litchfield On The Way
If you have time to explore another cute town on your drive back to Boston, I would suggest either tacking on a quick drive through the Litchfield Hills, CT if you didn’t already, or a stop in Sturbridge, MA. Sturbridge is more on the way to Boston, and offers beautiful foliage.
How to spend your time in Sturbridge, MA:
- Visit Old Sturbridge Village for all the cozy fall New England vibes (this is a must if you have time!).
- Pop into Saw Dust Coffee & Dessert Bar for lunch and treats.
- Sip on craft beer at Altruist Brewing Company.
And of course, as mentioned in the previous day’s itinerary, the Litchfield Hills region has plenty to offer for foliage views, small towns, and beautiful scenery.
But, if you have a flight to catch, then don’t risk it, and head straight to the airport! 🙂
Optional Adjustments For The 10 Day Itinerary:
- You can easily cut out Acadia National Park, and head straight to New Hampshire, and choose to spend more time there. Acadia is out of the way, and further north, so I know it doesn’t suit everyone’s plans. This would allow you time to definitely ride The Cog, and have a more relaxed schedule.
- If you would rather have more time in Vermont, you can skip The Berkshires/CT. This is personal preference! Both areas are amazing for fall foliage, but nothing is quite like Vermont in the fall. This would allow you time to move at a slower pace. If you decide to skip The Berkshires/CT and stay in Vermont for a third night, see my 12 day itinerary, option 3 for suggestions on what to do!
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 in 1 day to see Litchfield, CT after The Berkshires. Since you have the extra time, you can definitely see the Litchfield Hills region of Connecticut with this itinerary! I would recommend this option for those who really want to see as much of New England as possible, and make all the rounds.
Option 2: Add an extra day to Littleton/Franconia. This region has so many great hikes and places to spot fall foliage. It’s well worth adding a day to this part of the trip if you have the extra time. This would allow you a half day to ride The Cog, and takes more scenic walks and hikes to enjoy the fall foliage.
Option 3: Add an extra day to Vermont. On your extra day, you can take a day trip to Burlington and Shelburne, or spend the day driving the back roads.
Burlington & Shelburne, Vermont things to check out:
- 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.
- In Burlington, check out the waterfront area, and walk along Lake Champlain.
- Burlington also has an awesome craft brewery scene, and Foam Brewers is especially great.
- The American Flatbread restaurant in Burlington is a cozy place to stop for lunch.
- Church Street Marketplace in Burlington is a must!
- 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.
Vermont back roads driving itinerary near Stowe:
This drive is easier to do from Stowe, but it’s also doable from Woodstock if you’re okay with a longer day. This itinerary is is order based on departing from Stowe, but you can also adjust based on which town you’re coming from 🙂
- The covered bridges in Montgomery, including Montgomery covered bridge (which is actually in Waterville), and Longley Covered Bridge.
- Barn Owl Bistro is a hidden gem nearby that’s a great little pitstop.
- The town of Cabot and the nearby AM Foster Covered Bridge are really beautiful areas to visit full of rustic Vermont charm.
- Peacham is a very small town with iconic landscapes and scenery.
- Bogie Farm in East Ryegate is a landscape that worthy of a postcard, and is especially beautiful in the fall.
- The drive between all these destinations will also be lovely and scenic, and packed with fall color.
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, but eliminates Acadia National Park to save time.
7 Day Road Trip Overview
Day 1: Arrival In Boston
Day 2: Drive To Jackson, NH + A Stop In Salem, MA
Day 3: Drive To Franconia Along The Kancamagus Highway
Days 4-5: Drive To Stowe or Woodstock, VT + Stay 2 Nights
Day 6: The Berkshires
Day 7: Return To Boston
For this itinerary, you can also eliminate The Berkshires, and stay an extra night in Jackson or Franconia.
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! 😂), 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.
Vermont Fall Road Trip Itinerary
Looking to just see Vermont? Excellent choice. It’s my personal favorite fall destination in New England (even though it’s a very close call 😉)
For a Vermont fall road trip, you can really do it in anywhere from 5-7 days. Of course, more is better to really see everything, but generally speaking, you can actually make it happen in a week or less.
A popular route to take in Vermont is Route 100, which runs the entire length of state, right through the middle. This allows you opportunities to veer off and see some other places as well.
For the purpose of this itinerary, I’m going to provide a week-long (7 day) itinerary, and you can adjust it to your own plans.
Day 1: Bennington & Manchester
Day 2: Drive to Woodstock, stopping in Grafton and Weston on the way
Day 3: Spend the day in Woodstock
Day 4: Drive to Stowe, stopping in Montpelier if you’d like
Day 5: Spend the day in Stowe
Day 6: Staying in Stowe, take a day trip to Burlington & Shelburne
Day 7: Drive back
Day 1 Suggestions: Bennington and Manchester are pretty close to each other, so you can easily do both in one afternoon. There are some wonderful covered bridges in the area to see, and here are some more things to check out:
- The Bennington Battle Monument for fall foliage scenery.
- Downtown Bennington for shopping on Main Street (small, but cute!).
- Apple Barn is a few minutes from Main Street for a fun country store and bakery.
- Zoe’s in Manchester for lunch (great sandwiches!)
- Downtown Manchester for shopping in a cute town (don’t skip Northshire!)
Day 2 Suggestions: Grafton is a very small town, but it’s quintessential Vermont. It has a cute little cheese shop, and a nice little market/cafe called MKT Grafton, which is perfect for a quick bite. Also, swing by Weston to visit the Vermont Country Store.
For the rest of the itinerary, refer to the 10 day option for details 🙂
Click here to check out my post on a Vermont covered bridges road trip!
New Hampshire Fall Road Trip Itinerary
My second favorite fall foliage destination!
Here’s my suggested itinerary for a New Hampshire-only fall road trip.
To just see New Hampshire, you can also spend anywhere from 4-7 days.
With 4 days, you can easily just stick to the White Mountains region, but I’m here to give you all my tips on even more awesome places to see in the fall season in New Hampshire ☺️ So, this itinerary will be 7 full days, but adjust as you need to!
Day 1: Portsmouth
Day 2: Lake Winnipesaukee
Days 3-4: Littleton/Franconia
Days 5-6: North Conway/Jackson
Day 7: Drive back
Connecticut Fall Road Trip Itinerary Option
If you’ve seen all the “hot spots” around Vermont, New Hampshire, Massachusetts, and Maine, and you’re looking to explore a new part of New England in the fall, Connecticut should be next on your list!
As mentioned, my favorite place in Connecticut for fall foliage is the Litchfield Hills region. I always like to share that this region was what inspired Amy Sherman-Palladino’s creation of Stars Hollow, so Gilmore Girls fans will especially love this area.
The Litchfield Hills is very compact, and you can easily do a lot in a weekend here. However, 3-4 nights will allow you a nice, leisurely pace to explore all the amazing things this region has to offer in the fall.
The best towns to stay in in the Litchfield Hills region are:
- Litchfield
- New Milford
- Washington/Washington Depot
- Kent
Of all these towns, Litchfield probably has the most options when it comes to shopping and dining, however, they’re all very quaint and charming. I would pick whichever one has the best hotel for your plans.
If you have extra time for your Connecticut fall road trip, you can tack on places like Canaan to the north of the Litchfield Hills region, drive to Glastonbury, and then through the River Valley region, which includes the adorable towns of Chester and Essex. You can also choose to end your road trip in Mystic.
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).
Layers. The best way to dress in the fall season is with layers. Under your rain gear, flannels, sweaters, and lightweight t-shirts (both short-sleeved or long-sleeved) work great.
Jeans. These work really well for most days. Fall in New England is pretty casual.
Hiking clothing. For any hikes you want to do, pack whatever clothes you typically wear and feel comfortable in 🙂
Comfortable 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.
Dinner outfits. New England is home to incredible places for farm-to-table dining, some of which are a bit more fancy. If you plan to go out for a nice dinner or two, you’ll want to pack accordingly. New England isn’t super fancy, so women can do a casual dress/jeans and a nice top with booties in the fall, and men can easily do dark-wash jeans and a button down top.
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.
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.
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 in 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.
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
- Vermont In The Fall: Festive Things To 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 Vermont Pumpkin Patches & Farm Stands To Visit In The Fall
- Awesome Corn Mazes In Vermont
- Where To Stay In New Hampshire In The Fall
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!
