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11 New England Road Trip Itineraries for Any Season

By AFAR Editors

Jun 23, 2020

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

Photo by Trevor Fairbank/Shutterstock

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

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

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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 comprising the six states of Maine, Vermont, New Hampshire, Massachusetts, Connecticut, and Rhode Island, New England is filled with picturesque seaside towns, soaring mountains, clear lakes, and yep, some of the best fall foliage around. Consider this your guide to getting around safely and responsibly, and get ready to hit the road.

Summer New England Road Trips

Rhode Island Sand and Surf
Distance: 41 miles

Though this road trip from Beavertail State Park to Westerly is just 41 miles, we guarantee it will take longer than you think. Take in the scenic shoreline at the 153-acre Beavertail State Park, then head through Jamestown and west to Narragansett, working your way south along the coast, stopping in Charlestown’s East Beach for some more surf time. End the day with veranda cocktails at the grand five-star Ocean House, set on 13 acres overlooking the Atlantic, with views of Montauk and Block Island.

Coastal Maine
Distance: 272 miles

Much like California, Maine is also known for its stretch of Route 1, which crawls along the coastline and passes through Ogunquit, Kennebunk, Portland, Rockport, and more up until it hits New Brunswick, Canada. Must-dos along the way: Eat at the Clam Shack, located on the bridge between Kennebunk and Kennebunkport, snap a photo for the ’gram at Portland Head Light, and visit Project Puffin Audubon Center in Rockland—especially fun with kids in tow.

Vermont 100
Distance: 200 miles

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.) Quaint 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. 

Old King’s Highway in Cape Cod
Distance: 58 miles

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, we’re partial to the Sesuit Harbor House, originally built in 1735. 

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

Fall New England Road Trips

Kancamagus Highway, New Hampshire
Distance: 56 miles

Curving 56 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 bevy of picturesque ponds, hiking trails, scenic overlooks, and hairpin turns. Colloquially known as the “Kanc,” the byway draws millions of visitors every year.

Small Towns of Vermont
Distance: 25 miles

This road trip—along the state’s Route 7A—is tucked between the Taconic Mountains and Green Mountains, running parallel to the Long Trail. Bookended by the towns of Bennington and Manchester, the route stretches nearly 30 miles, passing attractive towns and farms with the mountains as a backdrop. 

Mohawk Trail, Massachusetts
Distance: 63 miles

Massachusetts’s Berkshire Mountains and its famed 63-mile Mohawk Trail are the stuff of leaf-peeping legends. Start in 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—which is where the views only keep getting better.

Park Loop Road, Acadia National Park, Maine
Distance: 7 miles

To take in views of the mountains and the colorful foliage, start at Hulls Cove Visitor Center (Bar Harbor) and drive up the summit of Cadillac Mountain. At the base of the mountain, suggests writer Melanie Haiken, stop by the 187-acre Jordan Pond, which “provides a wash of color against two rounded hills known as the Bubbles, which offer a spectacular view of a multi-hued treeline in the backdrop.”

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

Winter New England Road Trip

Skiers’ Paradise, Vermont
Distance: 80 miles

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, which has been open for more than 130 years.

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

Spring New England Road Trips

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Bold Coast Scenic Byway, Maine
Distance: 125 miles

Starting in the fishing village of Millbridge and ending in another fishing village, Eastport, the Bold Coast Scenic Byway runs 125 miles. What to expect? Lots of crashing waves, lobster wharfs, picturesque lighthouses, and boats bobbing in the water. Stops include the Burnham Tavern Museum—a National Historic Site, thanks to its role in the American Revolution—and Lubec, the easternmost town in the United States.

Quiet Connecticut
Distance: 40 miles

If you’re a fan of quaint towns and farmsteads, this road trip from Old Norwich to Woodstock might be for you. (Fun fact: Woodstock has more dairy farms than anywhere else in the state.) Though the route on CT169 clocks in at 40 miles, you’ll want to slow down and take your time—yep, it’s that scenic. Tranquility, is that you?

>> Next: A Guide to the World’s Best Road Trips

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