31 Ways to Fall for Autumn

From late September to the end of October, New England puts on a seasonal show like nowhere else—and stunning foliage is just the beginning.

By Kate Whouley

Aug 26 2021


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

Photo Credit : Lauren Blackwell/Red Leash Photo
A rural foliage display in Maine’s northernmost county, Aroostook
Photo Credit : Lauren Blackwell/Red Leash Photo

1. Go north.

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. The First Mile monument and lookout in Canada-hugging Fort Kent offer some great photo ops, but the quirkier treat is found en route: the largest 3-D model of the solar system in the western hemisphere, stretched across 40 miles of Route 1 between Presque Isle and Topsfield. Designed in conjunction with the University of Maine, the model boasts planets built by the residents of Aroostook County. 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. Visit Wood Prairie Family Farm in Bridgewater, where they specialize in organic seed potatoes. (That means you can grow your own at home.)

And be sure to stop by the Bouchard Family Farm in Fort Kent to pick up some of its famous buckwheat flour, milled on-site, which is the essential ingredient when making ployes, a delicious flatbread invented by the French Acadian exiles who settled in northern Maine. Dolly’s Restaurant in Frenchville is where locals will send you for ployes hot off the griddle. You can 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.

Get caught in a snowstorm of migrating geese.
Photo Credit : Jeff Nadler

2. Get caught in a snowstorm of migrating geese.

As recently as 20 years ago, locals and visitors in Vermont’s Champlain Valley can remember wing-packed skies in late October, when upward of 20,000 greater snow geese were on the move. Thanks to the designated refuge within the Dead Creek Wildlife Management Area in Addison County, the snow geese and other migratory birds have all the protected habitat they need to rest and refuel for their arduous journeys.

These days there are closer to 5,000 snow geese passing through, due to changing migration patterns, but that’s more than enough to inspire awe in earthbound humans. And you’re likely to spot any number of other avian residents and visitors too, with recent autumn sightings including peregrine falcons, rough-legged hawks, northern harriers, and bald eagles. Stop by Dead Creek’s visitor center to get the latest birding news and pick up a guide to walking trails and canoe access points. Or just head directly to the pull-off viewing site, on Route 17 in Addison, and look to the sky. As with all natural events, some days will be breathtaking, others may disappoint—but the anticipation is worth it.

3. 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.

4. Embrace organic at the Common Ground Country Fair.

*Editor’s note: Organizers of the Common Ground Country Fair announced September 1 that the in-person event would be canceled for 2021, with hopes of returning in 2022. 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.

5. Touch the foliage canopy.

Or feel as if you can, anyway, as you 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.

Float above the foliage.
Photo Credit : Coppola Photography/courtesy of Connecticut Office of Tourism

6. Float above the foliage.

Here’s a new perspective on those fleeting fall colors: Berkshire Balloons in Plainville, Connecticut, 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.

7. Find 100 reasons to take a drive.

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.

Ride the rails to color—and a rib-sticking meal.
Photo Credit : Herb Swanson

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

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.

9. G0 Trekking for antique treasure.

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.)

10. Rise with the moose.

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.

Mount Holyoke College, South Hadley, MA
Photo Credit : Wayne Moran Photography

11. Get schooled in autumn beauty.

With its 250-plus colleges and universities, New England is packed with well-appointed campuses that are perfect for autumn strolls. One of the loveliest of them all is Mount Holyoke College, founded in 1837 in South Hadley, Massachusetts. The oldest of the schools that compose the fabled Seven Sisters, Mount Holyoke has a trail system that features a loop past the wetlands that serve as an ecology lab for its students, as well as several loops through hardwoods and hemlocks on Prospect Hill. Don’t miss the college’s botanic garden, an indoor and outdoor collection of more than 2,000 types of plants, including natives and exotics from around the world.

The c. 1890 Fuller Bridge, one of half a dozen scenic spans in Montgomery, VT
Photo Credit : Sara Gray

12. Trip-trap across some covered bridges.

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

13. 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.

14. Cycle the kingdom.

Vermont’s Northeast Kingdom boasts 2,000 square miles of autumn beauty, including a network of “loops and links” conveniently mapped out for road cyclists of all abilities, courtesy of the Northeast Vermont Development Association.

Time your touring right, and you can also hit the Northeast Kingdom Fall Foliage Festival, which is actually a series of mini festivals held over seven consecutive days in Walden, Cabot, Plainfield, Peacham, Barnet, Groton, and Marshfield.

Taste the maple, then take the tram.
Photo Credit : Susan Laughlin

15. Taste the maple, then take the tram.

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.;

Autumn morning in Kent, CT.
Photo Credit : Mark Fleming

16. Leaf-peep in Hollywood’s New England.

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.

17. Make tracks to the desert.

No camels are required for a jaunt into the sand dunes at the 8,319-acre Big River Management Area in West Greenwich, Rhode Island. Where once stood a stone quarry, all that remains is sand and the feeling that you are somewhere else entirely, perhaps on the moon. Think of it as a palate cleanser amid the visual feast that is New England’s autumn foliage—which you can also find amid the woodlands and wetlands of the rest of this vast preserved open space.

18. Go on a johnnycakes journey.

Each fall, Kenyon’s Grist Mill in West Kingston, Rhode Island, makes a fuss over the humble corn fritter known as the johnnycake—a name derived from “journey-cakes,” as they were dubbed by the early New Englanders who packed them into their pockets on trips. Kenyon’s is Rhode Island’s oldest manufacturing business, with roots that date back to 1696. On festival days, Kenyon’s offers mill tours and johnnycake demos, among other amusements. To remember your visit, snag some freshly ground meals, flours, and mixes. (And by the way, we hear the famous Kenyon’s clam cake mix is life-changing.)

Be wooed by Woodstock.
Photo Credit : Oliver Parini

19. Be wooed by Woodstock.

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.

20. Take a road less traveled by.

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.

For loftier views, take the auto road at Rollins State Park up the slopes of Mount Kearsarge. From the parking area, there’s a half-mile hiking trail to the exposed granite summit, but the vistas are almost as amazing from the wooded picnic area, where you can dine and spy the summits of Pack Monadnock, Crotched, and Uncanoonuc, and, on a perfectly clear day, a slice of Boston’s skyline.

Local celeb Grayson the Yorkie at the Howl-o-Ween Pet Parade in Salem, MA
Photo Credit : Jaime Campos/The Salem News

21. Get spooked in Salem.

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.

22. Lose the crowds and love the lobster at Two Lights.

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.;

Light up the Night.
Photo Credit : Courtesy of Roger Williams Park Zoo

23. Light up the Night.

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.

Take Connecticut by land and by water.
Photo Credit : Allie Marsh

24. Take Connecticut by land and by water.

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.

Wet-harvesting cranberries at A.D. Makepeace in Wareham, MA
Photo Credit : Kim Houdlette for the A.D. Makepeace Company

25. Bask in bog beauty.

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.;

Heading out on a Sunset Stables trail ride in Lincoln Woods State Park.
Photo Credit : Courtesy of Sunset Stables

26. Saddle up or paddle away at Lincoln Woods.

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).

27. Pick your apples to a beat.

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.

28. Dig deep in Boston.

Here’s a city foliage outing with a generous helping of history you may have missed in school. The 1.6-mile Black Heritage Trail wends its way through the northern slope of Beacon Hill, formerly the West End, which in the 1800s was home to Boston’s largest free African-American community. With 14 sites in all, this walk through historic Boston streets highlights several stops on the Underground Railroad as well as former homes, schools, churches, and businesses of free Blacks and abolitionists.

29. Drink a toast to autumn.

“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.

30. Hit artistic heights.

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?

31. Sail a schooner into the sunset.

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.