• Kennebunkport, Maine fall foliage
    Fall foliage view of Kennebunkport, Maine

New England Fall Tour

Five States, Two Weeks, One Fabulous Fall

Come visit five New England states as the foliage paints the landscape with a vibrant palette. As the weather cools, the deciduous trees swap out the greens of summer for a new wardrobe of gold, crimson, orange and purple. This itinerary takes you through five states with numerous stops, perfect to take time to hop on a bike or hike a mountain to see the foliage from a different vantage point. Click the map image below to view the tour in Google Maps.

Trip ideas and itineraries are meant as suggestions only. They are intended as ideas and to highlight all there is to see and do in New England.

New England States - Two Week Fall Foliage Driving Tour
  • This route takes in five New England states and, since the distances between our stopovers are short, there is time to enjoy one of our top tips in each.
  • Start and finish in Boston, Massachusetts.
  • Spend a couple of days here to see the sights. The “T,” the public transport system, is efficient and inexpensive – and Boston is the most walkable major U.S. city. So, you don’t need to rent a car until you are setting off.
  • Driving distance: About 850 miles/1,400 km.
  • Allow 2 weeks.

Leave Boston, Massachusetts and follow the coast through New Hampshire to Maine and the resort town of Kennebunkport (85 miles/140 km).

Boat in Autumn - Kennebunkport, Maine (credit-Bob Dennis)

The Kennebunks, Maine

The popular vacation destination known as “The Kennebunks” includes Kennebunk, Kennebunkport, Arundel, and Cape Porpoise. In the fall, the fiery foliage contrasts with the blue of the Atlantic Ocean.


  • Take a ride: Horse-drawn carriage rides are a fun way to see the historic district of Kennebunkport.
  • Go birdwatching during busy fall migration: Nearby nature reserves include the Wells Reserve at Laudholm and the Rachel Carson Wildlife Refuge. Carson’s book, Silent Spring, helped trigger the environmental movement.

Head inland to Maine’s unspoiled mountains and Sebago Lake (50 miles/80 km).

Songo River Queen - Sebago Lake, Maine

Sebago Lake, Maine

This lake, whose name means “great stretch of water,” covers some 45 square miles (116 sq km). Nearby are smaller bodies of water: all reflect the surrounding woods, which are dazzling in autumn.

  • Climb that mountain: Short but steep is the trail leading to the summit of Douglas Mountain (1,415 ft/430 m), Sebago. The panorama takes in the White Mountains and Sebago Lake.
  • Cruise on a paddle steamer: The Songo River Queen II departs from Naples and heads along Long Lake.

Continue into New Hampshire, through rugged scenery. Stay in or near Colebrook, New Hampshire (100 miles/160 km), exactly halfway between the North Pole and the Equator!

Gorham, New Hampshire (Credit-Debbie Ryan)

Gorham, New Hampshire

Surrounded by the spectacular White Mountains, this is a great base for hiking, cycling and mountain biking, as well as zip lining and playing golf (ten courses close by). Attractions include the Mount Washington Auto Road, Great Glen Trails, Wildcat Mountain, Mount Washington Observatory and the Appalachian Mountain Club's Pinkham Notch Visitor Center with free shuttles available for hikers.


  • Drive north on Route 16. In the Great North Woods region, go through 13 Mile Woods to Umbagog Lake, the source of the Androscoggin River.
  • Ride the Moose Bus. See moose in their natural habitat. Leave from the Gorham Information Booth on the Town Common. Reservations recommended (through October).

1405-20-Cornish Windsor Bridge - credit: NH Div of Travel and Tourism Development

Cornish, New Hampshire

In the 19th century, Cornish was a summer artists’ colony. Most famous was sculptor Augustus Saint-Gaudens (statues of Lincoln, the Robert Gould Shaw Memorial). The Saint-Gaudens National Historic Site preserves his former home, studio, artworks, and garden.


  • See the view: You can drive almost to the top of Mount Ascutney (3,144 ft/960 m); walk the last mile to the summit. Watch the hang gliders!
  • Cross over the bridge: Built in 1866, the Cornish-Windsor Bridge is the longest wooden covered bridge in the U.S.A. (449 ft 5in/137 m) and also the longest two-span covered bridge in the world!

Cheshire Lake, Cheshire, MA; photo courtesy of Berkshire Visitors Bureau

North Adams, Massachusetts

Thanks to MASS MoCA, this former mill town is now one of the most visited places in the United States dedicated to new art. In 1999, the Massachusetts Museum of Contemporary Art opened in a vast disused factory complex, offering art, dance, music, film, and more.


  • Have fun: Fall festivals in North Adams range from a children’s parade and horse dressage to the arts.
  • Commune with nature: Near Florida (!) and north of Route 2, the Monroe State Forest has trails and wonderful vistas.

Drive through the Berkshire Hills, taking Route 8 instead of popular Route 7. Cross into Connecticut, the Litchfield Hills and head for Torrington (75 miles/125 km).

Mohawk State Forest, Cornwall, Connecticut (Credit-CT State Parks)

Torrington, Connecticut

In Torrington, the lovingly-restored Warner Theatre (now an arts complex) is just one of many Art Deco buildings. Add in the Nutmeg Conservatory for the Arts (ballet) and the No Place Like Home History Museum (local history) and you have a fun and buzzy arts destination.


  • Hike the trail: In Mohawk State Forest and adjoining Mohawk Mountain State Park, the higher you go, the better the views – as far as the Catskill, Taconic, and Berkshire ranges.
  • Go on safari: At Action Wildlife, see animals from all over the world on a drive-thru safari – in your own car!

Drive across to northeastern Connecticut, dubbed the Quiet Corner. A typical community is Putnam (90 miles/145 km).

Putnam Connecticut - credit Discover Putnam

Putnam, Connecticut

Nowadays, Putnam is known for its antiques shops, with everything from bric-a-brac to highly collectible furniture. But, this was also an important mill town: learn more on the River Mills Heritage Trail walking tour.


  • Be an explorer: With its 35 communities, farms, and forests, the unspoiled Last Green Valley is part of the Quinebaug and Shetucket Rivers Valley National Heritage Corridor.
  • Pick your own: Check out festivals in towns such as Brooklyn; join in Walktober events, such as pick-your-own apples or visits to corn mazes and wineries.

Drive down Route 169, one of the prettiest in the state. Then head into Rhode Island and the seaside village of Wickford (45 miles/75 km).

Fall Foliage in Newport, Rhode Island (credit - Discover Newport)

Wickford, Rhode Island

With 300 years of history, Wickford is delightful: churches, Colonial homes, gardens, antiques shops, galleries, restaurants – and a town dock! It was also the setting for local author John Updike’s The Witches of Eastwick – inspiring the Wicked Week festival in October.


  • Cruise Narragansett Bay: From Quonset Point, North Kingstown, join a cruise to see lighthouses, islands, the Jamestown and Newport Bridges, Newport Harbor, mansions, historic Fort Adams and more.
  • Rent a kayak for the afternoon and paddle about Wickford Harbor.
  • Stroll historic Newport: No city in America crams more history into its quaint streets, from Colonial days to the Gilded Age mansions.

Drive over the Jamestown and Newport Bridges to Rhode Island’s sleepy East Bay and Little Compton (35 miles/55 km).

Gold Barn - Rhode Island Department of Tourism

Little Compton, Rhode Island

Three centuries of history beckon in Little Compton, where homes are grand and meadows manicured. On the village green are a post office, library, school, and Wilbur’s General Store (since 1893).


  • Grape expectations: One of several vineyards along the Coastal Wine Trail is Sakonnet, with its regular tours and tastings of award-winning Chardonnays, and Gewurztraminers.
  • Visit tiny Sakonnet Harbor: A handful of boats still go out fishing from here every day.

Drive into Massachusetts and head for Sandwich, the first and oldest town on Cape Cod – established in 1639 (60 miles/100 km).

Cranberry processing - Credit-Cranberry Harvest Celebration - Massachusetts

Sandwich, Massachusetts

Nicknamed “The Museum Town," Sandwich offers several outstanding attractions: Heritage Museums & Gardens, the Sandwich Glass Museum and the (working) Dexter Grist Mill.


  • Visit a cranberry bog: On farms run by members of the Cape Cod Cranberry Growers' Association you can see how bogs are flooded so that the berries float for “wet picking.” October features the annual Cranberry Harvest Celebration.
  • Take a royal drive: What is now Route 6A is also known as the Old King’s Highway, linking villages, historic homes, antiques stores, and charming B&Bs.

Return to Boston, Massachusetts (60 miles/100 km).

Other New England Fall Foliage Drives: