New England may be known for its autumn reds and yellows, but to us, there’s no bad time to cross the region by car. Officially consisting of the six states of Maine, Vermont, New Hampshire, Massachusetts, Connecticut, and Rhode Island, New England is filled with picturesque seaside towns, mountains, clear lakes, and yep, some of the best fall foliage around. To see the region’s most beautiful sites, head out on one of these great New England road trip itineraries.
1. Vermont Route 100
- Start: Heartwellville, Vermont
- End: Troy, Vermont
- Distance: 217 miles
- Recommended season: summer
At 217 miles long, the Scenic Route 100 Byway hugs the eastern edge of the Green Mountains and travels nearly the entire length of Vermont. (Most of Vermont’s ski resorts are located along the highway, so it can actually have fewer cars in the summer than in winter.) If cute old-school stores are your thing, be sure to stop at the Vermont Country Store in Weston—it’s been open since 1946 and offers free cheese and maple syrup samples.
Dramatic scenes like these are delightfully par for the course along Maine’s coast.
Courtesy of Stephen Crane/Unsplash
2. Maine State Route 9 East
- Start: Ogunquit, Maine
- End: Calais, Maine
- Distance: 263 miles
- Recommended season: summer
Much like California, Maine is also known for its stretch of Route 1, aka “the lobster trail.” This trip crawls along the coastline and passes through Ogunquit, Kennebunk, Portland, Rockport, and more until it hits Canada. Must-dos along the way: Eat at the Clam Shack, on the bridge between Kennebunk and Kennebunkport, snap a photo at Portland Head Light, and stop by Project Puffin Visitor Center in Rockland—especially fun with kids in tow.
Cape Cod is known for its appealing beaches and coastline.
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3. Old King’s Highway in Cape Cod
- Start: Sandwich, Massachusetts
- End: Provincetown, Massachusetts
- Distance: 60 miles
- Recommended season: summer
Route 6A is popular in summer, when visitors to the Massachusetts Cape begin their trip in Sandwich and follow the road east to Provincetown, passing cranberry bogs, salt marshes, historic homes, and some of the oldest villages in the United States. Get your lobster roll fix at places like Kate’s Seafood (Brewster) and Arnold’s Lobster & Clam Bar (Eastham). For overnights, head over to South Dennis and stay at the Sesuit Harbor House, originally built in 1735.
The Kancamagus Highway is known for being one of the top spots to see fall foliage.
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4. Kancamagus Highway, New Hampshire
- Start: Conway, New Hampshire
- End: Lincoln, New Hampshire
- Distance: 35 miles
- Recommended season: fall
Curving for 35 miles on country roads through New Hampshire’s White Mountain National Forest, the Kancamagus Highway has earned its place on several “best of” road trip lists, thanks to its picturesque ponds, hiking trails, scenic overlooks, and hairpin turns. Colloquially known as the “Kanc,” the byway draws millions of visitors every year. With the highway’s plentiful hiking trails taking up daylight, spend the night in one of the six White Mountain National Forest campgrounds located on the byway.
This road trip passes through quaint towns like St. Johnsbury, Vermont.
Photo by Snehit Photo/Shutterstock
5. Connecticut River Byway
- Start: South Hadley, Massachusetts
- End: Pittsburg, New Hampshire
- Distance: 242 miles
- Recommended season: fall
Another way to reach New Hampshire’s White Mountains is to take the Connecticut River Byway, which is Vermont’s only designated National Byway. The route cuts from South Hadley, a little college town home to Seven Sisters school Mount Holyoke, straight up through Vermont to the top of Vermont and then just east to New Hampshire. Along the way, stop by some of Massachusetts’s historic district villages like Northfield and Montague Center, or take a few nature-led detours to Molly State Park near Brattleboro, Vermont. (The food co-op here is a good place for picnic fare.)
If you’re unable to do the whole route, no worries. In the words of Afar deputy editor Tim Chester: “Pick a stretch and you can’t go wrong—particularly in fall when the leafy backdrop is painted shades of red, orange, and yellow.”
End your road trip in Burlington, Vermont’s most populated (and delightfully walkable) city.
Photo by Julie Deshaies/Shutterstock
6. Burlington to Woodstock, Vermont via I-89 S
- Start: Burlington, Vermont
- End: Woodstock, Vermont
- Distance: 90 miles
- Recommended season: fall
While several road trips on this list go through Vermont, this road trip itinerary specifically focuses on the state’s delicious dishes. Starting in Burlington, road-trippers can visit the local farmers’ market for breakfast before continuing south on Route 89 to Stowe. Around here, try places like Long Trail Brewing Company and Hen of the Wood (dinner only). The drive concludes in Woodstock, where you can find salted goat’s milk caramels at Fat Toad Farm.
7. Mohawk Trail (Route 7), Massachusetts
- Start: Pittsfield, Massachusetts
- End: Greenfield, Massachusetts
- Distance: 63 miles
- Recommended season: fall
Massachusetts’s Berkshire Mountains and its famed 63-mile Mohawk Trail are the stuff of leaf-peeping legends. Starting in Pittsfield, take Route 7 north until hitting Williamstown, home to Williams College and art museum the Clark, and continue on Route 2 to Western Gateway Heritage State Park, Natural Bridge State Park, and MASS MoCA, among other attractions. Eventually, you’ll hit the Hoosac Range—where the views only keep getting better. For a stay along the way, consider Miraval Berkshires in Lenox.
Stowe is one of the East Coast’s top ski destinations.
Photo by FashionStock.com/Shutterstock
8. Skiers’ Paradise via Route 100, Vermont
- Start: Stowe, Vermont
- End: Woodstock, Vermont
- Distance: 80 miles
- Recommended season: winter
Come winter, heavy snow drifts mean good things for skiers in New England. Visit several ski resorts on this road trip—including Stowe Mountain Resort and Saskadena Six Ski Area—which starts in Stowe and finishes in Woodstock, Vermont. It’s 80 miles between the two towns on Vermont Route 100 (allow two hours) or 73 miles on the highway (allow an hour and 20 minutes); the slopes—and attractions—in each mean you’ll want to spread the trip out over a long weekend. Things not to miss in Stowe: the family-run Alchemist brewery, Stowe Maple Products sugarhouse, and the thin-crust pies at the aptly named Piecasso.
In Woodstock, be sure to carve out time for Richardson’s Tavern, Billings Farm & Museum, and F.H. Gillingham & Sons, a store that has been open for nearly 140 years.
The manicured gardens at Roseland Cottage are prettiest in spring.
Photo by Lee Snider Photo Images/Shutterstock
9. Quiet Connecticut via I-395 N
- Start: Norwich, Connecticut
- End: Woodstock, Connecticut
- Distance: 39 miles
- Recommended season: spring
If you’re a fan of quaint towns and farmsteads, this road trip from Norwich to Woodstock might be for you. (Fun fact: Woodstock has more dairy farms than anywhere else in the state.) The route, on I-395 N, clocks in at 39 miles, but you’ll want to slow down and take your time—yep, it’s that scenic. Do some bird-watching at Aicher Preserve or Border Woods Preserve, both of which come alive with greenery and flowers in spring. The manicured gardens will be in full bloom at Roseland Cottage in Woodstock, a pretty 1846 Gothic revival–style former summer home that’s a history museum. Bed down for the night at the Inn at Woodstock Hill, where you can enjoy Connecticut’s serenity near the small town of Putnam.
This article originally appeared online in 2020; it was most recently updated on August 14, 2024, to include current information.
