There’s something magical about New England in the fall: the crisp air, pumpkin everything, and those fiery leaves. It’s the kind of season that begs for scenic drives, sweater weather, and a little adventure.
If you’re dreaming of coastal towns, cozy vibes, and alllll the lobster rolls and cider donuts, this road trip is about to become your new fall obsession.
Let’s dive into the ultimate 10-day New England fall road trip through Massachusetts, Maine, New Hampshire, and Vermont!
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Planning Your Trip
As you plan your New England fall road trip, use Expedia to find the best flight and accommodation prices and book your entire trip in one spot!
PS Expedia Group brought the family closer with a unified and expanded loyalty program called One Key, and it’s not just for Expedia. Hotels.com and the vacation rental site, Vrbo, are all part of the fun!
When you’re a One Key member, you can earn OneKeyCash for every dollar you spend on eligible hotels, vacation rentals, activities, dreamy packages, car rentals, and even epic cruise adventures.
Boston to Portland
Boston Logan International Airport to Portland, Maine (Approx. 1 hr 49 mins | 106 mi)
We landed early enough to pick-up our rental car and drive straight to Portland.
Portland is a charming coastal gem with a quirky, laid-back vibe that’s impossible not to love. Picture cobblestone streets lined with redbrick buildings, a working waterfront buzzing with fishing boats, and a food scene that will blow you away.
Top Places to Stay in Portland
Day 1: Portland
Kick off your New England fall road trip by diving into all this coastal city has to offer. From iconic lighthouses to adorable boutique-lined streets, Portland has the perfect blend of history, culture, and flavor.
Foodies, prepare to fall head over heels, Portland is a culinary dream come true.
Whether you’re sipping craft brews or savoring fresh lobster rolls, you’ll find yourself reminiscing about them long after your trip wraps up.
Day 2: Portland to North Conway
Portland, Maine to North Conway, New Hampshire (Approx. 1 hr 30 mins | 63 mi)
North Conway is an outdoor lover’s dream located in the heart of the White Mountains.
The moment you arrive, it’s hard not to fall in love with the stunning mountain views, the quaint downtown shops, and the cozy cafés dishing out warm cider that feels like autumn in a cup.
Take a scenic drive along the Kancamagus Highway, explore local trails, or hop aboard the Conway Scenic Railroad for a nostalgic ride through the mountains.
Top Places To Stay in North Conway
Day 3: Flume Gorge
North Conway, New Hampshire to Flume Gorge, New Hampshire (Approx. 1 hr | 46 mi)
If you’re visiting Flume Gorge during fall foliage season (aka peak season), you’ll need to book your entry time in advance, like, MONTHS in advance! Trust me, you don’t want to miss this, so plan ahead!
And aim to arrive early to enjoy the trail before the crowds roll in.
Top Things to Do in and Around Flume Gorge
- Hike the 2.2-mile Flume Gorge trail, a family-friendly path with waterfalls and covered bridges. Most people take about 1.5 hours, but if you’re with kids, plan for extra time to explore and enjoy snack breaks.
- Visit Artist’s Bluff Lookout for more stunning views.
- Grab a bite at Polly’s Pancake Parlor. But here’s the thing about Polly’s, it’s POPULAR. By 11 a.m., the wait was already 2.5 hours (seriously, pancakes are that good!).
Day 4: The Kancamagus Scenic Byway To Woodstock
Kancamagus Scenic Byway (Approx. 45 mins – half day | 34.5 mi).
Lincoln, New Hampshire to Woodstock, Vermont (Approx. 1hr 30 mins | 83 mi)
The “Kanc”, aka The Kancamagus Scenic Byway, winds through the beautiful White Mountains.
This might just be one of the most scenic drives in the US, especially if you’re coming during fall foliage season!
You can drive the byway without stopping in about 45 minutes, but you’ll wanna plan for at least half a day, if not a full day, to explore it to the fullest.
After enjoying the byway, it’s time to head to Vermont!
Top Stops Along the Kancamagus Byway:
Top Things To Do Along The Kancamagus Scenic Byway
- Before hitting the road, make a stop at Frontside Coffee Roasters for breakfast on the go.
- Visit the Albany Covered Bridge for a classic photo op.
- Hike to Sabbaday Falls and enjoy the waterfall views.
- Stop at the Panoramic Overlook.
- Check out Lower Falls for a peaceful stop by the water.
- Explore the Rocky Gorge Scenic Area for impressive rock formations.
- Take in the views at Sugar Hill Scenic Vista.
- Snap photos at Hancock Overlook.
- Lunch at Woodstock Inn Brewery or White Mountain Bagel Co in Lincoln
Top Places to Stay in Woodstock
Day 5: Woodstock
Woodstock, Vermont, is the quintessential New England town that is home to cute shops, and cafes, and it’s so festive during foliage season.
With its charming covered bridges, quaint boutiques, local farms, and tree-lined streets, it’s the perfect mix of small-town charm and countryside.
It’s a must-visit for anyone looking for that classic Vermont experience!
Top Things To Do In Woodstock
- Shop at the Farmer’s Market on the Green (open every Wednesday).
- Visit Billings Farm to meet some dairy cows and other farm animals.
- Indulge in some Maple Creemee (a maple soft serve ice cream) from Woodstock Scoops.
- Stop by F.H. Gillingham & Sons General Store to browse for local goods like maple syrup.
- Grab a delicious sandwich from The Village Butcher Shop, a fantastic deli with quality meats and cheeses.
- Dinner at Simon Pearce Restaurant. When we visited it was already fully booked (two months in advance!!!) so plan ahead.
Day 6-7: Woodstock to Stowe
Woodstock, Vermont to Stowe, Vermont (Approx. 1hr 20 mins | 73 mi)
Tucked into the Green Mountains, Stowe just screams New England in the fall, think fiery foliage, orchards, and all the cider donuts you can handle.
Hike through trails surrounded by autumn leaves, explore the charming downtown filled with boutique shops and historic inns, or simply take in the breathtaking views from spots like Smugglers’ Notch or the top of Mount Mansfield.
And don’t forget to indulge in farm-fresh treats or check out some local breweries!
Top Things To Do In Stowe
- Visit the family-owned Hunger Mountain Orchard, located halfway between Woodstock and Stowe. This is a must-visit with little ones and for taking cute photos.
- Have breakfast at Black Cap Coffee & Bakery for delicious pastries.
- Enjoy cider donuts, freshly-pressed cider, and delicious homemade foods at Cold Hollow Cider Mill. You can book your spot and order lunch the day before here.
- Check out the quaint Middle Covered Bridge.
- Wander around Montpelier.
- Stop by Ben & Jerry’s factory for ice cream or book the 30-minute factory tour.
- Visit the scenic trails, cascading waterfalls, and serene pools at Moss Glen Falls.
- Grab a Heady Topper IPA at The Alchemist Brewery.
- Admire the gorgeous Stowe Community Church.
Top Places to Stay in Stowe
- Trapp Family Lodge (Yep, the real Von Trapp Family Lodge!)
- Green Mountain Inn
- The Stowe Village Inn
Day 8 – 10: Boston
Stowe, Vermont to Boston, Massachusetts (Approx. 3hr 24 mins | 204 mi)
Boston is the grand finale of your New England fall road trip!
Walk the Freedom Trail for a step back in time, wander the streets of Beacon Hill, or treat yourself to fresh seafood by the waterfront.
Whether it’s catching a game at Fenway or soaking in the views from Boston Common, Boston has plenty of things to do, including kid-friendly activities!
Top Things To Do In Boston
- Walk the Freedom Trail.
- Book a Boston Duck Tour (this was super fun!).
- Spend the morning at the Museum of Science (great with kiddos!).
- Stroll around Beacon Hill.
- Visit Boston Public Library.
- Check out the museums, in particular the Isabella Stuart Gardner Museum.
- Shop at Newbury Street.
- Hang Out at Fenway Park.
- Stroll along Boston Harborwalk.
And for my fellow foodies, Boston doesn’t disappoint!
Top Places To Eat In Boston, MA
- Tatte Bakery & Cafe – For pastries and coffee (seriously, it’s that good, we ate here almost every morning!)
- Coterie in the Four Seasons – A chic spot for brunch or dinner with fresh, seasonal dishes and an upscale vibe.
- Saltie Girl –A Seafood lovers’ paradise with oysters, lobster rolls, and cocktails.
- Map Room Lounge – Located in the Boston Public Library it’s the perfect spot for tea or craft cocktails and small bites.
- Boston Public Market – An indoor market with artisanal foods, fresh meals, and local snacks.
- Parish Cafe – Inventive sandwiches named after famous chefs, perfect for lunch.
- Quincy Market – Historic food court with local flavors and international dishes.
- Legal Sea Foods (especially at the Burlington Mall) – Fresh seafood and New England classics like clam chowder.
Top Places to Stay in Boston, MA
Watch now!
Check out my Instagram Reel’s of our New England fall road trip!
Day 1: PortlandDay 2: Portland to North ConwayDay 3: Flume GorgeDay 4: The Kanc to WoodstockDay 5: WoodstockDay 6-7: Woodstock to StoweDay 8 -10: Boston
And there you have it, 10 days of pure autumn magic on this New England fall road trip! From dreamy foliage drives and hiking trails to cider donuts and lobster rolls, this itinerary checks all the fall boxes.
Happy road-tripping!
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