11 Beautiful Road Trips for Exploring New England

This article originally appeared online in 2020; it was most recently updated on August 28, 2026, to include current information.

I live in Massachusetts, so I never need much of an excuse to hop in the car and explore the Bay State along with the other five states that comprise New England: Maine, Vermont, New Hampshire, Connecticut, and Rhode Island. Sometimes, travelers mistakenly believe that autumn—with its sweep of gorgeous red, gold, and orange leaves—is the absolute best time to visit. And while it is spectacular here in the fall, New England dazzles all year long. The region is filled with indigenous roots, Revolutionary history, picturesque seaside towns, mountains, clear lakes, and, yes, some of the most compelling fall foliage around. To see the area’s most beautiful sites, head out on one of these New England road trip itineraries.

Vermont Route 100

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At 217 miles, 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 along the highway, so it can actually have fewer cars in the summer than in winter.) If cute old-school shops are your thing, be sure to stop at the Vermont Country Store in Weston. It’s been open since 1946 and offers complimentary cheese and maple syrup samples. Or visit Cabot Creamery Store in Waterbury. While you may be familiar with some of Cabot’s products, you might not realize it’s a farmer-owned cooperative. Free samples are available here, too.

Maine Coastal U.S. Route 1

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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 (closed mid-December through April)—especially fun with kids in tow. Stop for lunch at nearby seasonal seafood shack, Claws.

Old King’s Highway in Cape Cod

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Old King’s Highway, also known as 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 the Cape House (Brewster) or Arnold’s Lobster & Clam Bar (Eastham). For overnights, head over to South Dennis and stay at the Sesuit Harbor House, originally built around 1735.

Kancamagus Highway, New Hampshire

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Curving for 35 miles on country roads through New Hampshire’s White Mountain National Forest, the Kancamagus Highway (part of New Hampshire Route 112) 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 seven White Mountain National Forest campgrounds on the byway.

Connecticut River Byway

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Another way to reach New Hampshire’s White Mountains is to take the Massachusetts portion of the Connecticut River Byway, which continues on through Vermont and is that state’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 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 Stark 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 travel writer 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.”

Burlington to Woodstock, Vermont via I-89 S

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While several road trips on this list go through Vermont, this 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.

Mohawk Trail (routes 2 and 2A), Massachusetts

Massachusetts’s Berkshire mountains and its famed Mohawk Trail are the stuff of legends for leaf lookers. Starting in Pittsfield, take Route 7 north until hitting Williamstown, home to Williams College and the Clark Art Museum, and continue on Route 2 to 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.

Skiers’ Paradise via Route 100, Vermont

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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 (at Woodstock Inn & Resort), Billings Farm & Museum, and F.H. Gillingham & Sons, a store that has been open since 1886.

Quiet Connecticut via I-395 N

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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.

Route 102, Rhode Island

Don’t let Rhode Island’s small size fool you—the state, known fondly by locals as “Little Rhody,” packs a punch when it comes to scenic views and historic charm. Route 102, running from North Smithfield and ending in Wickford, offers coastal views, historic sites, and small towns with vibrant main streets all in one 44-mile stretch. Fuel up for your trip by taking a short detour to Wright’s Dairy Farm & Bakery, a family-run bakery that’s been serving up fresh pastries, ice cream, and milk since 1914. Then explore Slatersville, America’s first planned industrial mill village, where you can wander through its historic center complete with restored mill homes. End your trip in the pretty coastal town of Wickford by wandering down its boutique-lined main street or renting a kayak from the Kayak Centre to explore its sailboat-freckled harbor.

Moose Path Trail, New Hampshire

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If you’ve ever hoped to see a moose in the wild, this scenic byway running from Berlin (just north of the White Mountains region) all the way up to the Canadian border, might just be your best chance at spotting the large mammal. The route winds its way up into what’s known as Moose Alley, a 13-mile stretch between Pittsburg and the Canadian border that curves around dense forests, wetlands, and several lakes. The area is home to northern New Hampshire’s moose herd of 3,000 to 4,000 strong, and the likelihood of seeing them are higher if you head out at dusk or dawn. Stretch your legs on the Falls In The River Trail, which will bring you even deeper into Moose Alley, or rent a kayak or canoe to explore the Connecticut Lakes.