9 New England Road Trip Itineraries for Any Season

Whether it’s spring, summer, fall, or winter, there’s a road trip (or two) for each season.

Distant view from water of large historic house on coast

View of Horsehead-Marbella, an historic house near Beavertail State Park.

Photo by Trevor Fairbank/Shutterstock

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 100

  • Start: Heartwellville
  • End: Troy
  • Distance: 200 miles
  • Recommended season: summer

At 200 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 winter.) Cute country stores your thing? Be sure to stop at Vermont Country Store in Weston—it’s been open since 1946 and offers free cheese and maple syrup samples.

Rocky cove along Maine’s coast, with a few evergreens

Dramatic scenes like these are par for the course along Maine’s coast.

Photo by Shutterstock

2. Coastal Maine

  • Start: Ogunquit
  • End: Calais
  • Distance: 272 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 for the ’gram at Portland Head Light, and visit Project Puffin Visitor Center in Rockland—especially fun with kids in tow.

Dunes in Cape Cod, MA at sunset with a small group of people in the background

Cape Cod is known for its beautiful beaches and coast line.


3. Old King’s Highway in Cape Cod

  • Start: Sandwich
  • End: Provincetown
  • 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.

Aerial view of the Kancamagus Highway curving through red, yellow, and green forest

The Kancamagus Highway is known for being one of the top spots to see fall foliage.

Photo by Shutterstock

4. Kancamagus Highway, New Hampshire

  • Start: Conway
  • End: Lincoln
  • Distance: 34.5 miles
  • Recommended season: fall

Curving for 34.5 miles on country roads through New Hampshire’s White Mountain National Forest, this drive 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.

A view of the small town, St. Johnsbury, Vermont in the fall with green and orange trees in the foreground and two white buildings with towers in the background.

This road trip passes through quaint towns like St. Johnsbury, Vermont.

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. Along the way, stop by some of Massachusetts’s historic district villages like Northfield and Montague Center, or take some nature-led detours to Molly State Park in Vermont.

If you’re unable to do the whole route, no worries. In the words of AFAR 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.”

A view of the church and a wide, red brick road in Burlington, Vermont Church Street Marketplace downtown city. Fall trees that are orange and yellow line the road on the right and left side.

End your road trip in Burlington, Vermont’s capital.


6. Burlington to Woodstock, Vermont

  • Start: Burlington
  • End: Woodstock
  • Distance: 132 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 concepts like Long Trail Brewing Company and Hen of the Wood. The drive concludes in Woodstock, offering local fare from Fat Toad Farm.

7. Mohawk Trail, Massachusetts

  • Start: Pittsfield
  • End: Greenfield
  • 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 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 the Tourists hotel in North Adams.

Winter in Stowe, Vermont, with a few skiers and ski lift among snowy evergreens

Winter in Stowe, Vermont, one of the leading ski destinations on the East Coast

Photo by Shutterstock

8. Skiers’ Paradise, Vermont

  • Start: Stowe
  • End: Woodstock
  • Distance: 80 miles
  • Recommended season: winter

Come winter, heavy snow drifts mean good things for skiers in New England. Visit two of the best ski resorts on the East Coast on this road trip, which starts in Stowe and finishes in Woodstock, Vermont. It’s a mere 80 miles between the two towns, but 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 more than 130 years.

9. Quiet Connecticut

  • Start: Norwich
  • End: Woodstock
  • Distance: 40 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 road clocks in at 40 miles, you’ll want to slow down and take your time—yep, it’s that scenic. Do some birdwatching at Aicher Preserve or Border Woods Preserve before staying at the Inn At Woodstock Hill, where you can enjoy Connecticut’s serenity near the small town of Putnam. Tranquility, is that you?

This article originally appeared online in 2020; it was most recently updated on August 9, 2023, to include current information.

Chloe Arrojado is the associate editor of destinations at AFAR. She’s a big fan of cafés, dancing, and asking people on the street for restaurant recommendations.
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