10 Best Fall Road Trips in New England

It’s hard to imagine a more beautiful time of year in New England than the fall, when rich swaths of red, orange, and yellow make the landscape glow. It’s a season when apple orchards, farm stands, corn mazes, agricultural fairs, hot cider doughnuts, and quiet coastal towns all beckon with their sights, sounds, and aromas. For maximum fun, a foliage-inspired road trip is a great way to make the most of autumn New England. So grab your camera, make a playlist, and get ready. Here are the 10 best New England road trip routes for fall — some big and busy, and some just the right amount of quiet.

10 Best New England Road Trip Routes for Fall

Vergennes to Montpelier, Vermont

Yankee has called this fall road trip “a roller-coaster ride through the heart of Vermont.” Starting in. Starting in Vergennes, the state’s oldest city, fill up with a hearty breakfast at 3 Squares Café before traveling east on Route 17 through farmland with views of South Mountain and Mount Ellen. Arriving in Bristol, you’ll find a number of shops celebrating the work of local artists, such as Art on Main. Continue on to admire the sweeping views from the top of Appalachian Gap before hitting Waitsfield, where you’ll follow the Mad River, then the Winooski River, to reach Montpelier, the smallest state capital in the country. There, make time to grab lunch (if you arrive before 2 p.m., try Down Home Kitchen, a 2017 Yankee Editors’ Pick), then head to Hubbard Park for a short hike and views of the city. Nearby Morse Farm Maple Sugarworks offers Vermont gifts, cheese, maple syrup, and maple creemees. Distance: About 60 miles one way.

Want more? Find complete directions for this Vermont fall road trip, plus additional things to see and do, here.

Whitefield to Wiscasset, Maine

Starting in the Midcoast town of Wis­casset, leave behind the hustle and bustle of Red’s Eats, the town’s legendary lobster roll spot, for a scenic jaunt along Route 218 and the Sheepscot River to North Whitefield and back. Notable pull-over options en route include the 1811 Lincoln County Museum & Old Jail, the Sheepscot General Store (for fresh produce or something to nibble on from the café), and the Sheepscot Valley Brewing Company (note: tasting room open weekends only). Distance: About 40 miles round-trip.

Want more? Find complete directions for this Maine fall road trip, plus additional things to see and do, here.

Lake Winnipesaukee Loop, New Hampshire

Offering glimmering waters bordered by jewel tones of autumn color, New Hampshire’s largest lake, Winnipesaukee, and its smaller neighbor to the northwest, Squam, provide the ideal backdrop for a gentler Granite State road trip than the mountainous Kancamagus. Plus, this lake loop offers arguably more opportunities for shopping and snacking. Start in Alton Bay, at Lake Winnipesaukee’s southern tip, then head west on Route 11 toward the lively boardwalk scene at Weirs Beach. Ice cream fans will love the sundaes at the Swiss-inspired Kellerhaus. Head north to Meredith, where the League of New Hampshire Craftsmen and Moulton Farm are just two of the many spots worth pulling over for. Continue up to serene Squam Lake, where the 1981 film On Golden Pond was filmed, then cruise through charming Sandwich and Moultonborough (be sure to stop for a bag of penny candy at the Old Country Store & Museum). On the northern shore of Lake Winnipesaukee you’ll breeze into Wolfeboro, whose Main Street beckons with shopping, good food, and lake views. A final stretch south brings you back to Alton Bay. Distance: 75 miles round-trip.

Want more? Find complete directions for this New Hampshire fall road trip, plus additional things to see and do, here.

South Hadley to Turners Falls, Massachusetts

Following the Connecticut River through Western Massachusetts, this New England road trip feels like taking a journey back in time. Starting in South Hadley, grab coffee and a pastry at the Thirsty Mind coffeehouse to get fueled up for your trip. Heading north on Route 47, admire the cows grazing at Barstow’s Longview Farm in Hadley, then drive through Skinner State Park to the summit of Mount Holyoke for river views. The North Hadley Sugar Shack is the go-to for stocking up on all things maple-y and sweet, while a Route 116 detour to the top of Mount Sugarloaf in South Deerfield offers spectacular lookout-tower views of the river and the Holyoke Range. Back on Route 47, continue north to Montague for a stop at the Montague Bookmill, hailed by Yankee as one of the best used bookstores in New England, to enjoy a leisurely browse and lunch at the mill’s café. Farther north, Turners Falls offers more strolling opportunities and, at 2nd Street Baking Co., an impressive roster of breads, cupcakes, and pastries. Distance: About 50 miles (with summit detours).

Want more? Find complete directions for this Massachusetts fall road trip, plus additional things to see and do, here.

Farm Coast, Rhode Island and Massachusetts

Tucked between Cape Cod and Newport, the Farm Coast region of southeastern Massachusetts and Rhode Island is a place that Yankee has called “a slice of picture-perfect country life reserved for New Englanders in the know.” Start in the village of Padanaram, in South Dartmouth, Massachusetts, for lovely views of Apponagansett Bay. As you head west, cornfields and stone walls lead to Westport, where the 380-acre Westport Rivers Winery offers tastings and tours, and Osprey Sea Kayak Adventures provides the chance to rent a kayak and paddle around the Westport River. Ready for refreshments? The Head Town Landing Country Store is a popular spot for coffee, homemade doughnuts, ice cream, and Del’s Frozen Lemonade. At the border, the small village of Adamsville, Rhode Island, is home to the historic Grays’ Grist Mill. You can pick up a bag of stone-ground jonnycake meal before continuing on to the Commons Lunch, in charming Little Compton, for a plate of the real deal. After filling up, stroll the grounds of the white-steepled Union Congregational Church and the Old Commons Burying Ground for a dose of history. Mosey north on Route 77 past Walker’s Roadside Stand (though you may want to stop for produce, pumpkins, and fresh flowers) to the rural artist haven of Tiverton Four Corners, a hidden gem that’s home to shops, galleries, and some of the creamiest scoops in New England at Gray’s Ice Cream. Distance: About 25 miles one way.

Want more? Find complete directions for this Massachusetts and Rhode Island fall road trip, plus additional things to see and do, here.

Granby to Goshen, Connecticut

History, sweeping scenery, and (what else?) fall color are the hallmarks of this winding route through the northwestern corner of Connecticut. Begin in Granby, about 20 miles northwest of Hartford. As you head west on Route 20, available stops include Honey Hill Pottery for a unique gift or Holcomb Farm for 13 miles of walking trails. Documenting your drive? A left onto Route 219 to Route 318 offers Instagram-ready views of Saville Dam, with its stone gatehouse and backdrop of sugar maples, oaks, and pines. Motor on through the American Legion State Forest before a stop at the Riverton General Store, at Hogback Dam, to enjoy coffee or sandwiches on the outdoor patio. Ten miles to the west lies Norfolk, home to Haystack Mountain State Park, where you can drive halfway up and then hike to the top (the 1929 tower offers views in all directions). Continue south on 272 to Route 4 toward Goshen, your last stop. Here, you won’t want to miss Thorncrest Farm, where the cows supply a key ingredient for Milk House Chocolates’ gourmet sweets. A box or two just might be the perfect New England road trip souvenir. Distance: About 55 miles on way.

Want more? Find complete directions for this Connecticut fall road trip, plus additional things to see and do, here.

Route 100, Vermont

Stretching 200 miles from Massachusetts to Lake Memphremagog at the Canadian border, Vermont’s Route 100 has been called the best foliage drive in the state — and even the most scenic foliage drive in all of New England. It’s a long stretch, so you may not be able to tackle it all in one day if you want to make a lot of stops (and you should). South-to-north highlights include the art galleries and craft stores in Wilmington, the famous Vermont Country Store in Weston, the President Calvin Coolidge State Historic Site in Plymouth Notch, samples of Ben & Jerry’s ice cream at the factory tour in Waterbury, and  just about everything in the mountain resort town of Stowe. Yankee may have summed up autumn on Route 100 best: “Leaf-peeping, after all, is about more than just leaves. It’s about the foliage experience — farmstands and country stores, craft galleries and hot cider — and Route 100, with its many off-the-beaten-path side trips, offers all of that in one long winding package.” Distance: About 200 miles one way.

Want more? Find additional things to see and do along Vermont’s Route 100 here.

Kancamagus Highway, New Hampshire

The Kancamagus Highway (Route 112) in New Hampshire has just about everything you could want in a scenic New England road trip. Crossing 30 winding miles of White Mountain forest from Conway to Lincoln, you’ll enjoy views of foliage-draped mountains, boulder-strewn rivers, and crystal-clear ponds. Start your day in Conway with breakfast at the Stairway Café, a 2016 Yankee Editors’ Pick, or take a provisions-focused swing through Zeb’s General Store. Favorite stops along the Swift River include the Albany Covered Bridge, Lower Falls, and Rocky Gorge and Falls Pond. Continuing on, the Kanc climbs nearly 2,500 feet before reaching a pair of truly breathtaking overlooks, one facing east (C.L. Graham Wangan Overlook) and one facing west (Pemigewasset Overlook). Finally, you descend into Lincoln for a bite at another Yankee favorite, Gypsy Café. Distance: About 50 miles one way.

Want more? Find additional things to see and do along the Kancamagus Highway here.

Mohawk Trail, Massachusetts

The Mohawk Trail, one of the nation’s first official “scenic tourist routes,” has been a favorite New England road trip since it first opened in 1914. While technically it represents the northwest section of Route 2, stretching from Millers Falls to the New York border, the real action happens between the towns of Greenfield and Williamstown, where mountains, rivers, farmland, and quintessential small towns make up the scenery. Favorite stops include the Bridge of Flowers and candlepin bowling in Shelburne Falls, the photogenic entrance to the 1870s Hoosac Tunnel in Florida, the view of the Connecticut River from Mount Sugarloaf in South Deerfield, the Hail to the Sunrise monument in Charlemont, and the Clark Art Institute in Williamstown. But that’s just barely scratching the surface. As Yankee put it: “The Mohawk, one of the oldest scenic byways in the country, doesn’t so much blast around territory as bring you into it, slicing through Berkshire villages and some of the most scenic beauty in all of New England, maybe the country.” Distance: About 42 miles one way (Greenfield to Williamstown).

Want more? Find additional things to see and do along the Mohawk Trail here.

Park Loop Road, Acadia National Park, Maine

The Park Loop Road, located on the eastern side of Mount Desert Island, is a great New England road trip for nature lovers and foliage enthusiasts alike, offering both mountain vistas and coastal foliage views of Acadia National Park. Start at the Hulls Cove Visitor Center in Bar Harbor and continue on, choosing from such popular stops as Jordan Pond and the drive-up summit of Cadillac Mountain. Distance: 27 miles.

Have a great suggestion for an autumn New England road trip? Share your favorite routes below!

This post was first published in 2017 and has been updated. 

SEE MORE:
10 Places to Visit in New England in Fall
Best Fall Food Festivals in New England
10 Best Summer Road Trips in New England

Aimee Tucker

Aimee Tucker is Yankee Magazine’s Senior Digital Editor. A lifelong New Englander and Yankee contributor since 2010, Aimee has written columns devoted to history, foliage, retro food, and architecture, and regularly shares her experiences in New England travel, home, and gardening. Her most memorable Yankee experiences to date include meeting Stephen King, singing along to a James Taylor Fourth of July concert at Tanglewood, and taking to the skies in the Hood blimp for an open-air tour of the Massachusetts coastline.

More by Aimee Tucker