Ultimate Fall in New England Road Trip – 4 Days of Leaf Peeping, Covered Bridges & Scenic Drives
Crisp air, amazing red and orange foliage, charming small towns, and winding scenic byways. New England in the fall is a feast for the eyes. If you're dreaming of the perfect autumn escape, this road trip through Massachusetts, New Hampshire, and Vermont packs in peak foliage, covered bridges, farm stands, and small-town charm. Let’s hit the road!
GETTING HERE
Make it stand out
If you don’t live within driving distance of New England, Boston Airport is where you’ll want to fly into, especially if you want a direct flight. However, I always like to check costs of flying into smaller airports like Burlington, Vermont (then do the trips backwards). Flights can be expensive since visiting for fall foliage is very popular. I recommend booking flights by early August or set alerts on Google Flights
You have to have a car for this itinerary. Book your rental car early. Like flights, car rental prices also rise sharply in September/October.
WHEN IS THE BEST TIME TO VISIT TO SEE FALL COLORS?
We have visited New England several times in the Fall. The first trip we visited a week or so after peak fall foliage. It was stunning. Because we visited lower states like Rhode Island and Connecticut which were just hitting their peak season, we were able to see leaves in all stages of color over our five-state road trip. On our second trip in 2021, we timed it a little too early. The leaves were beginning to turn, but we had to drive as far north as we could in Vermont and New Hampshire to really see the color. On our third trip, we hit it right, but heavy rains took all the leaves off the trees before we arrived.
I like to refer to this Fall Foliage map when planning our trip. You just plug in the dates of your stay and it tells you what stage of color the leaves will be in. Remember, the map is just a guide and that foliage color is based on many factors including summer temps and rainfall. We booked our second trip based on the map saying it was peak foliage when in fact it was probably still a week or two away. When in doubt, book your trip for a week after peak foliage. For us, we were able to see much more color by arriving a week later.
We have visited New England in the Fall three times in the past five years. Each time, visiting a new town and going different routes. This is our favorite itinerary for a long weekend in New England to see all the Highlights you’ve seen social media. If you have more time, I would add a long stop in Salem, Mass at the end, it’s just 30 minutes outside of Boston for a Halloween experience like no other. You can read my Guide to Salem here.
Day 1: Boston to the conway, NH
Our fall road trip always begins in Boston. This is where we find the cheapest flights and cheapest rental cars. It takes about two and a half hours to get to Conway, New Hampshire which the official starting point of the iconic Kancamagus Scenic Byway.
If you arrive early in Boston, I recommend starting the scenic drive on this day. But if your flight gets in later, plan to stay the night in Conway and start your drive early the next morning. If you stay the night in Conway, head to North Conway for dinner and exploring. They have the cutest shops. Put Zeb’s General Store in your GPS to find out where to go.
Before you start the Kancamagus scenic drive, stop at the White Mountains Visitor Center right at the entrance. Pick up a map and ask a Ranger about any cool stops and bridge locations.
The Kancamagus scenic drive is a 34-mile drive to Lincoln, NH and is nothing short of spectacular. Expect lots of fall color, winding roads, sweeping mountain views, and plenty of pull-offs. Be prepared for lots of traffic and tour buses if you head out too late. Be sure to check out:
Albany Covered Bridge
Rocky Gorge Scenic Area
Sabbaday Falls
We always stay the night in Lincoln, NH. This is a cute ski resort town with a lot to do. We use points to stay at the Holiday Inn Express every year. The rate includes breakfast. There are lots of food options here too. We had a great meal at The Common Man restaurant.
Day 2: Franconia Notch State Park & Stowe, VT
There are a ton of things to do in and around Lincoln, NH. You can take an hour long scenic train ride out of Lincoln (the parking lot is right across from the Holiday Inn where we stayed), but to pack in everything on this itinerary, I recommend heading straight to Franconia Notch State Park.
Franconia Notch State Park is home to Flume Gorge. We did the two-mile loop which is suitable for all abilities. If you follow me on Instagram, you’ll know that we almost skipped this because we didn’t want to pay the admission fee. Well, it was definitely worth it. On our hike we got to see waterfalls, two covered bridges, and explore the towering granite walls of the gorge. It’s like something that we’ve never seen before.
After our hike, we headed towards Stowe. If you have time, you can build in a stop to Echo Lake or climb up the viral Artist’s Bluff which is just down the road from Franconia Notch. You can’t miss all the people up on the rock. If this is a priority for you, I would do this first thing in the morning and then head to Flume Gorge where it’s less important how many people are there.
Stowe, Vermont is the town everyone thinks of when they think of fall in New England. We’ve stayed here twice. The first time we splurged and stayed at the Trapp Family Lodge, this is an alpine resort founded by the real Von Trapp family of Sound of Music fame. The rooms are super cute and there are fantastic views of Stowe and the surrounding mountains from up here.
A stay at the Trapp Family Lodge will transport you right to Austria in this alpine resort
If you stay here, don’t miss the daily history tour. It’s always hosted by a family member and is super interesting. Ours was led by Samuel, Maria Von Trapp’s grandson. Even if you don’t stay here, at least drive up and look around. Maria Von Trapp and her family are buried here, and you can stroll through the grounds.
Must see and do in Stowe:
Shopping in the village - we had no problems finding parking along the main street.
Visiting Cold Hollow Cider Mill - get here early, traffic gets bad, and lines get very, very long. Grab an apple cider donut. The line is long but moves fast.
Exploring Smuggler’s Notch - take the ski lift up for amazing fall color views
(Optional) Stop at Ben & Jerry’s Factory in Waterbury - you’ll drive by this on your way to Woodstock
There are three covered bridges in Stowe - see if you can find them all
Day 3: STOWE, VT to Woodstock, VT
On day three, we headed to Woodstock, Vermont. If you have time, stop in Montpelier, (the smallest U.S. state capital). This charming town is full of New England character, and you’ll find more church steeples than traffic lights. It’s a great place to stretch your legs and grab a coffee before continuing.
Woodstock is one of the most picturesque villages in New England. From the historic Middle Covered Bridge to the quaint town green, everything here feels like a postcard. We could spend days walking around and exploring but if you need more to see, hop in your car and drive up to Billings Farm and drive along Barnard Road and Pomfret Roads, this is where you’ll stumble across those gorgeous farms.
Must see and do in Woodstock:
See the Woodstock Inn, you can go inside and walk around. I recommend even walking around to the back. They have pumpkins everywhere.
Middle Covered Bridge (across the street from the Woodstock Inn)
Breakfast or coffee at Mon Vert Cafe
Stroll down Pleasant Street to find the little pumpkins on the white picket fence
Drinks at Au Comptoir
Explore the Marsh-Billings Rockefeller National Historic Park
While the road to Sleepy Hollow Farm is closed during peak foliage season now, all the winding roads back here have gorgeous homes, farms and surprises around every corner.
If you have more time:
Sugarbush Farm: This little farm is tucked away in the hills and is so idyllic. Great stop close to Woodstock. Learn how maple syrup is made, how they make block cheese. Great way to support a small business that’s been around for 80 years.
Billings Farm and Museum: This is a working dairy farm where you can view demonstrations and learn about Vermont Farming.
Where we stayed:
On our first visit to Woodstock my sister splurged, and we got to stay at the Woodstock Inn & Resort. It was absolutely fabulous!
When my daughter and I stayed here, we stayed at The Vesper Bed and Breakfast. Super cute, right on the edge of main street where we could walk to everything.
How cute is the Vesper B&B?
Day 4: Return to Boston
On your way back to Boston, make sure to stop at the Quechee Gorge right outside of Woodstock. It’s called Vermon’s Little Grand Canyon.
Don’t forget to pop into Salem, Mass if you have time. We saw the best fall foliage here!
TIPS FOR YOUR TRIP:
What to wear: Fall in New England can be chilly and rainy. I don’t like to carry an umbrella around, so I pack a good rain jacket with a drawstring hood. Make sure you wear rain boots or shoes that can get wet. Viewing fall colors means you’ll be outside a lot and remember the old saying “there’s no such thing as bad weather, only unsuitable clothing”.
No Service: Download Google Maps for the areas you’ll be visiting. There were many times we were driving down country roads where we had no service at all and just had to drive until we had service again to find out where we were. Learn from our mistakes and be prepared for being offline.
Book Early: Hotels book up quickly during peak Fall foliage. If you wait until the last minute, you may find the town you want to stay in is completely sold out! We booked our rooms in late July/early August and over 80% of lodging in the smaller towns were already sold out.
Travel Midweek: There is a huge difference in crowds (and hotel prices) during the week versus the weekend. If you have a flexible schedule, I highly recommend New England during the week.
Expectations: Set your expectations for color. All three times we’ve visited we were on the cusp of pre and post foliage, so we were flexible in being willing to drive further north (or south) to find color. This is a road trip so don’t be afraid to venture out to find that brilliant color you’re looking for.
Happy Fall Travels!