25 Memorable Things to Do in New England in Fall

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Heading to New England this autumn? Make the most of your foliage day trip, road trip, or weekend getaway with our list of memorable things to do in New England in fall, excerpted from the September/October 2021 Yankee Feature “31 Ways to Fall for Autumn” by Kate Whouley.

25 Memorable Things to Do in New England in Fall

25 Memorable Things to Do in New England in Fall

A rural foliage display in Maine’s northernmost county, Aroostook

Lauren Blackwell/Red Leash Photo

Go North to Aroostook County, Maine

No, really north—all the way to America’s First Mile in Fort Kent, Maine. That’s the spot where U.S. Route 1 begins its 2,369-mile journey to Key West, Florida. This is Maine’s largest and least populous region, with autumn vistas galore. Fall is also potato harvest time, when local high schoolers on “harvest break” still help out the local farmers. Stop by the Dolly’s Restaurant in Frenchville ployes, a delicious flatbread invented by the French Acadian exiles who settled in northern Maine, hot off the griddle. Then work them off with a short (and at times, rugged) hike up Haystack Mountain in Castle Hill, where the effort rewards you with 360 degrees of Aroostook’s golds, greens, and reds. visitaroostook.com

Go Foliage Ziplining at Bretton Woods, New Hampshire

Don’t miss the chance to zipline above the slopes of Bretton Woods, New Hampshire, on a leaf-peeping tour with a side of adrenaline. Traversing a network of platforms connected by nine ziplines, two sky bridges, and three rappels, you’ll soar among ancient hemlocks, pines, and spruces and enjoy breathtaking views of the White Mountains, including New England’s mightiest, Mount Washington. The canopy tours are offered by the Omni Mount Washington Resort, where the more earth-loving travelers in your party might prefer surveying the gorgeous vistas from the plush 25,000-square-foot spa. brettonwoods.com

Float above the foliage with Berkshire Balloons.

Coppola Photography/courtesy of Connecticut Office of Tourism

Take a Foliage Balloon Ride in Plainville, Connecticut

Here’s a floating new perspective on those fleeting fall colors. Berkshire Balloons offers early-morning hot-air balloon flights (7 a.m. in the autumn months), and once you’re up, up, and away, you’ll revel in above-the-treetops views spanning four states. Much depends on wind speed and direction, but expect to travel 5 to 15 mph at altitudes ranging from 500 to 5,000 feet. berkshireballoons.com

Find 100 reasons to take a drive.

Thomas Pajot/iStock

Drive Vermont’s Route 100

You’ll want to pull over—a lot—as you drive Vermont’s Route 100, which many consider the most scenic route in New England. Beginning at the Massachusetts line and traveling up the middle of Vermont almost all the way to the Canadian border, Route 100 offers more than 200 miles of forest color, mountain vistas, and idyllic New England villages, not to mention grazing cows, silver-capped silos, and sunlit fields shifting from green to gold before your eyes. Drive a stretch in a day, go longer and plan an overnight or two, or launch an annual pilgrimage to experience a brand-new segment year after year. vermontvacation.com

G0 Antiquing in Wiscasset, Maine

Midcoast Maine is where you’ll find Wiscasset, a historic village known for its seaside charm and wealth of antique shops—more than 40 in all, from the petite Lilac Cottage Antiques to the three-story Antiques Mall. It’s also home to beautiful examples of Federal and Victorian architecture, a trail system set amid 200 acres of woods and fields, a railway museum, and a bustling waterfront. (You won’t go hungry here either, given the presence of Red’s Eats and Sprague’s Lobster, which are both open through mid-October.) visitmaine.com

See More: 10 Best Antique Towns in New England

25 Memorable Things to Do in New England in Fall

Ride the rails to color—and a rib-sticking meal.

Herb Swanson

Hop Aboard a Lake Winnipesaukee Foliage Train

The Fall Foliage Special on the Hobo & Winnipesaukee Scenic Railroad offers four hours of car-free lake and mountain beauty. Departing from the northern end of Lake Winnipesaukee in Meredith, New Hampshire, you’ll travel along Lake Waukewan to crest the Ashland Summit, then chug through Bridgewater to arrive in Plymouth just in time for a buffet lunch at the Common Man Inn & Spa (think: roast turkey with all the fixings, meat lasagna, veggie stir-fry). Stash some fresh-baked cookies for the ride back, which includes a stop in Ashland for a guided tour of the restored 1869 Boston, Concord & Montreal Railroad Station. hoborr.com

See More: Best 5 Fall Foliage Trains in New England

See a Moose at Moosehead Lake

At last count, moose outnumbered humans by about 3 to 1 in Maine’s Moosehead Lake area, so your chances of sighting the region’s namesake critter are excellent. You can hop onto a 6 a.m. moose safari with Northeast Whitewater in Shirley Falls, which offers canoe tours and van excursions through October 13. Need your coffee before trekking into the wilderness? There are afternoon and evening outings too. northeastwhitewater.com

25 Memorable Things to Do in New England in Fall

The c. 1890 Fuller Bridge, one of half a dozen scenic spans in Montgomery, VT

Sara Gray

Drive Across a Covered Bridge

There’s something about these practical New England structures that feels a lot like magic. For maximum enchantment per square mile, head just south of the Canadian border to Montgomery, Vermont, where you’ll find six covered bridges in town and one right outside it, the most of any town in the country. montgomeryvt.us

See More: The Best Covered Bridge in Every New England State

Hop a Trolley to a Pumpkin Patch

On autumn weekends at the Connecticut Trolley Museum in East Windsor, Connecticut, it’s pumpkins by day and scary ghouls by night. (Rails to the Darkside, the “haunted” nighttime trolley ride, is recommended only for ages 16 and up.) Before or after your ride, you can explore the museum’s collection of vintage trolleys, streetcars, locomotives, and fire trucks. Feeling the urge to pilot your very own trolley? Ask about the Guest Motorman Experience, including training, supervision, and a chance to impress up to four guests with your new skills. ct-trolley.org

25 Memorable Things to Do in New England in Fall

Taste the maple, then take the tram.

Susan Laughlin

Eat Pancakes at Polly’s Pancake Parlor in Sugar Hill, New Hampshire

Fuel up on fluffy homemade pancakes doused with local maple syrup at Polly’s Pancake Parlor in Sugar Hill, New Hampshire. Then set out for Franconia Notch State Park, where in addition to hiking the Flume and biking the trails, you can board an aerial tram for an eight-minute ride of wonder to the 4,080-foot peak of Cannon Mountain. On a clear day, you can see mountains as far away as Vermont, Maine, New York, and even Canada. pollyspancakeparlor.com; cannonmt.com

See More: Best Pancake Houses in New England

Drive the Currier & Ives Scenic Byway in New Hampshire

If you aren’t feeling up to tackling the traffic of New Hampshire’s most famous foliage highway, the Kancamagus, look to the Granite State’s quieter 40-mile Currier & Ives Scenic Byway to deliver timeless autumn landscapes. Photo ops abound in the route’s historic towns—Henniker, Hopkinton, Warner, Webster, and Salisbury—where you can soak up the village vibe, walk along one of the many local rail trails, or put in a kayak on the Contoocook. currierandivesbyway.org

See More: 14 Favorite Fall Drives in New England

Eat a Lobster Roll at Two Lights in Cape Elizabeth, Maine

Summer may be high season for visiting the coast, but for many, the quieter autumn “shoulder season” is actually better for sampling its delights. Aim for early or mid-October to relish a last lobster roll at the Lobster Shack at Two Lights in Cape Elizabeth, Maine (they usually close the weekend before Halloween). Dine at a classic red picnic table with a view of waves pounding on rocks, then head up the road to Two Lights State Park to explore its 41 acres, learn a little bit about Maine’s military history, and drink in the rugged beauty of the coast. lobstershacktwolights.com; maine.gov/twolights

See More: The Best Lobster Roll in Every New England State

Autumn morning in Kent, CT.

Mark Fleming

Leaf-peep in the Real Stars Hollow in Kent, Connecticut

Stars Hollow, the fictional setting of the cult-favorite TV show Gilmore Girls, was inspired by a visit to Connecticut’s Litchfield Hills—and even if you’ve never seen an episode, you’ll love the vibe and the views here. Look for the Gilmore-esque gazebo on the New Milford green, stroll through Kent’s charming town center, then head to Washington Depot to order a large coffee at Marty’s and browse the shelves of the venerable Hickory Stick Bookshop. You can even book a luxurious overnight at the Mayflower Inn in Washington, where Gilmore Girls creators Amy Sherman-Palladino and Daniel Palladino stayed for a weekend in the 1990s—and just look what happened. discoverlitchfieldhills.com

Be wooed by Woodstock.

Oliver Parini

Be Wooed by Magical Woodstock, Vermont

Nestled between Mount Tom and Mount Peg, the town of Woodstock, Vermont, has been hailed as “America’s prettiest small town.” But it’s plenty lively too, and packed with New England history. Highlights of an autumn stroll around the c. 1768 village include bright fall color on the green, inviting local shops, and the highly photogenic Middle Covered Bridge, one of three covered bridges you’ll find here. Be sure to stop into the eclectic general store F.H. Gillingham & Sons, founded in 1886 by the great-grandfather of today’s owners. Foodies, time your trip to coincide with the annual Apples & Crafts Fair & Food Truck Festival (10/9–10/10) to meet area artisans and sample local harvest foods. Not far from the village is Billings Farm & Museum, a nonprofit working dairy farm where visitors are welcome and parking is plentiful. Hang out with friendly farm animals, tour the restored c. 1890 farmhouse, sample some Billings Farm cheddar, or just breathe in the rolling pastures. woodstockvt.com

Local celeb Grayson the Yorkie at the Howl-o-Ween Pet Parade in Salem, MA

Jaime Campos/The Salem News

Get Spooked in Salem, Massachusetts

October in Salem, Massachusetts, feels like a never-ending block party chock-full of costumed visitors—think Mardi Gras with vampires—and it’s lots of fun to join. But there are also many fascinating things to discover here, from walking tours filled with historical and architectural highlights, to the Peabody Essex Museum, where art and history collide in intriguing ways. A tip for those based in Boston: Leave your car behind and board a high-speed ferry at Long Wharf, and you’ll be in Salem within 60 minutes, free of parking headaches during the town’s bustling Halloween season. salem.org

Embrace Organic at the Common Ground Country Fair in Unity, Maine

Blacksmithing meets reiki healing in this annual celebration of rural living held in Unity, Maine, and sponsored by the Maine Organic Farmers and Gardeners Association. Take in live demonstrations of revived folk and household arts, consult with an herbalist, watch herding dogs at work, or enter the Harry S. Truman Manure Pitch-off (register early and choose your competitive strength: accuracy or distance). Live music features local performers, including some of Maine’s premier fiddlers, who supply the sound for daily contradances. Before departing, check out at least one demo by the Wednesday Spinners, a group of Down East women who have gathered weekly in each other’s homes for decades to spin, dye, and weave. This year’s fair runs 9/24–9/26. mofga.org/the-fair

See More: 12 New England Fairs to Visit This Fall

Light up the Night.

Courtesy of Roger Williams Park Zoo

See the Jack-o’-Lantern Spectacular at Roger Williams Park Zoo in Providence, Rhode Island

While autumn wouldn’t be complete without flickering pumpkins, the Jack-o’-Lantern Spectacular at Roger Williams Park Zoo in Providence, Rhode Island, delivers enough to tide you over for a whole year. Follow a trail lined with more than 5,000 artisan-carved pumpkins, which are accompanied by eerie music and special effects to put you in a ghoulishly good mood. Those with little ones should check out the “family fun” nights, when fairy-tale characters and superheroes hang out among the jack-o’-lanterns. rwpzoo.org

See More: Best 5 Pumpkin Festivals in New England

Take Connecticut by land and by water.

Allie Marsh

Take a Riverboat Foliage Cruise in Connecticut

A one-of-a-kind journey begins at Essex Steam Train and Riverboat in Essex, Connecticut, when you board a steam train that carries you through unspoiled wetlands (birders, don’t forget your binoculars). In the town of Deep River you’ll move onto the Becky Thatcher, a 70-foot Mississippi-style riverboat, to cruise the Connecticut River and take in views of autumn foliage and historic landmarks such as Gillette Castle, Goodspeed Opera House, and the 1913 East Haddam Swing Bridge. Finally, it’s all aboard the train for the return leg. Offered weekends through October, this 2½-hour excursion is foliage trip, wildlife tour, and history lesson, all rolled into one. essexsteamtrain.com

See More: Guide to New England Foliage Cruises

25 Memorable Things to Do in New England in Fall

Wet-harvesting cranberries at A.D. Makepeace in Wareham, MA

Kim Houdlette for the A.D. Makepeace Company

Visit a Cranberry Bog in Massachusetts

While cranberries are a signature fall crop, unlike apple or pumpkin picking the harvest is not easily seen up close. Unless, that is, you book a tour with the Cape Cod Cranberry Growers’ Association, whose 300-plus members include many that do wet harvesting, a process that creates eye-catching floating carpets of berries. But the dry version is equally fascinating and beautiful—for proof, just head to Annie’s Crannies in Dennis, Massachusetts, the birthplace of the cultivated cranberry. Run by 12th-generation Cape Codder Annie Walker, the farm opens to visitors for five weekends in October and November and sometimes even lets them help out with the harvest. The gift shop is where to load up on cranberries to take home, as well as beeswax candles and honey from the beehives that dot the property. cranberries.org; anniescrannies.com

Heading out on a Sunset Stables trail ride in Lincoln Woods State Park.

Courtesy of Sunset Stables

Saddle Up at Sunset Stables in Lincoln, Rhode Island

Just 15 minutes from Providence, Rhode Island, this 627-acre state park was established more than 100 years ago and has been drawing outdoors aficionados ever since. To go beyond the standard biking or hiking exploration, rent a kayak to see wetland color from the water, or head to nearby Sunset Stables to mount up for a trail ride (a portion of the park’s trails have even been set aside for equestrians only). riparks.com

Pick Apples at Applecrest Farm in Hampton Falls, New Hampshire

There’s live music every weekend at the oldest continually operated apple farm in the country, Applecrest Farm in Hampton Falls, New Hampshire, where you can get a lift on a tractor to the apple orchard or the pumpkin patch to pick your own. Weekly fall festivals include pie-eating contests, storybook hayrides for kids, and pumpkin-carving demonstrations. If you don’t feel like picking your own apples, grab a peck at the farm market, which offers 40 varieties along with fresh-pressed apple cider; local honey, jam, and maple syrup; and just-picked fruits and veggies. applecrest.com

See More: 13 Best Apple Orchards in New England

Drink a Toast to Autumn at Saltwater Farm Vineyard in Stonington, Connecticut

“Runway Red” is just one of the options on offer at Saltwater Farm Vineyard in Stonington, Connecticut, where elegant small-batch wines compete for attention with a beautifully restored 1930s airplane hangar. The hub of tiny Westone Airport until about 1950, the hangar is now the Tasting Room, where you can enjoy wine, local craft beer, cider, and nibbles, with a stunning seaside vineyard view. saltwaterfarmvineyard.com

Go to Oktoberfest at Mount Snow in Dover, Vermont

Grab a stein, and commence yodeling. There are a few dozen German and domestic beers (including many New England favorites) to sample at the Mount Snow Oktoberfest, a Columbus Day weekend event in Dover, Vermont. You can also rock to a live oompah band, check out an arts and crafts show, and join the famous schnitzel toss. After polka-ing and pumpkin-painting, hop on a “flying sofa,” one of the six-passenger bubble chairs that make up the Bluebird Express. You’ll see some spectacular fall color on the seven-minute ride to Mount Snow’s 3,600-foot summit. mountsnow.com

Combine Art and Nature in North Adams, Massachusetts

A morning stroll through the large-scale exhibition spaces of Mass MoCA, the factory turned art museum in North Adams, Massachusetts, is the perfect prelude to an autumn hike at nearby Mount Greylock State Reservation, home of the state’s highest mountain as well as miles of mountain biking trails and hiking loops of varying difficulty. The reservation is accessible from the Western Gateway Heritage State Park complex, just a quarter-mile south of Mass MoCA. Fall shows at the museum include James Turrell’s C.A.V.U., Taryn Simon’s The Pipes, and Glenn Kaino’s In the Light of a Shadow. It’s a day where culture meets nature—how perfect is that? massmoca.orgmass.gov

Sail a Schooner in Newport, Rhode Island

After you board the 80-foot Aquidneck, the largest boat in Sightsailing of Newport’s touring fleet, you can help raise the sails and even take the helm—or just sit back and enjoy coastal color with a water view of Newport, Rhode Island’s Gilded Age grandeur. Morning, early afternoon, and sunset sails are available through early November, but book early to secure your spot (reservations open 21 days in advance). A reproduction of a 19th-century coasting schooner, the Aquidneck is fully equipped for contemporary comfort. That’s what we call smooth sailing. sightsailing.com    

A longer version of this list appeared in the September/October 2021 Yankee Feature “31 Ways to Fall for Autumn” by Kate Whouley.

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25 Memorable Things to Do in New England in Fall

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