Fall in New England is more than just beautiful leaves. It encompasses a variety of experiences, from apple picking and browsing farmers’ markets to visiting unique shops and, of course, sampling great food. After 75 years, Yankee goes out on a limb: We’ve broken down the foliage experience into 14 categories and given each town a score in every one of them. Using hard data, opinion, and lots of travel time, here are our rankings. Let the debates begin …
The Top 25 Foliage Towns in New England (and Thus the World!)
The Top 25 Foliage Towns in New England | The Best
Kent, Connecticut
In the foliage trip of our dreams, I wake to the smell of woodsmoke, stretch, and breathe in the crisp morning air: apple weather. Driving through hills that don’t so much roll as tumble along the banks of a twisting river, I stop for a thick hot chocolate and an authentic Belgian pastry to shake off the morning chill. Before the day is done, I’ll hike the Appalachian Trail, picnic on paninis by a waterfall, shop for Buddhas and modern art, and bite into a crisp native Cortland, perhaps in the shade of a historic covered bridge.
And I’ll do it all in one town in Connecticut. Despite the stiff competition that Vermont and New Hampshire villages put up every year for bragging rights to the best foliage town in New England—and, by extension, the world—I found the pinnacle of the leaf-peeping experience in the northwestern Connecticut town of Kent. Of course, that starts with great foliage: The profusion of crimson and gold that leaps off the Litchfield Hills to reflect in the winding course of the Housatonic River is at times nothing short of breathtaking.
But aren’t the leaves themselves really the McGuffin of the foliage experience—the plot device that serves as a mere excuse for our annual regional adventure? The heart of the New England leaf-peeping experience lies in the details: the farmstands and covered bridges, the waterfalls and antiques stores that provide the eye candy, framed by the colors of our most glorious season. All of these things Kent has in abundance, in a perfect blend of uncommon natural beauty and culture that might shame cities 10 times its size (just shy of 3,000 people in the 2000 census).
Only minutes away from the lovely walkable campus of the Kent School, there’s an artistic bent to downtown, from the spare modernism of Eckert Fine Art to the larger-than-life sculptures in the barn- like Morrison Gallery. In fact, sculptures from the latter spill out onto grass and sidewalk: a pair of giant bronze bulls at the town’s main crossroads, a chessboard with crested mountain lions for pawns in an otherwise-plain courtyard.
To bring home a little of that artistic sensibility, visit Heron American Crafts Gallery for artisanal wares from around New England and beyond. Look for the shadow-box sculptures of Tomas Savrda, which we guarantee are like nothing you’ve ever seen before. For impressive artwork and antiques from around the world—Balinese shadow puppets, woven African bowls, teakwood furniture—visit Foreign Cargo. Since 1970, the shop has been run by a family that has worked extensively in foreign aid and has used its connections and experience to source unique items from around the globe.
The profusion of art in town offers a constant counterpoint to the artistry of nature. Across the Housatonic River, Macedonia Brook State Park is carved into the side of Cobble Mountain, where Revolutionary-era residents dug iron ore out of the hills to fashion into cannonballs to fire at the British. (A more extensive homage to Kent’s industrial past, the Sloane– Stanley Museum, is up Route 7.) The strenuous seven-mile blue loop trail scrambles up and down granite outcroppings, while the three-mile orange trail offers a more relaxed hike through birches and sugar maples. The foliage is as spectacular as anywhere in New England, both close up in the tunnel of trees along the trails as well as in the vistas over the surrounding hills. If you want something more leisurely, follow the Housatonic “River Walk,” almost five miles of flat terrain hugging the water along the Appalachian Trail.
After my hike, I stop nearby at aptly named Mountain View Farm, which boasts an enviable vista along with a bevy of organic produce. There I meet Maria LaFontan, who has been working the land with her husband, Vincent, for 10 years here, and now farms eight fields of pumpkins, squash, garlic, heirloom tomatoes, and other crops, along with raising a flock of some 85 chickens. It’s the only place in Connecticut she’s aware of, she tells me proudly, where you can purchase certified organic maple syrup.
Kent’s other big natural draw tumbles 200 feet down from the hills in a series of cascades known collectively as Kent Falls (ct.gov). Despite the wild- ness of the water, the surrounding area is quite civilized, with wooden stairs studded with viewing platforms ascending alongside, and a wide grassy field at the bottom that draws dozens of locals and tourists on fall weekends to picnic and socialize. To join them, I pick up the aforementioned panini at, well, Panini, a pint- size café and “gelateria” on Kent’s main green that serves hot-pressed goodness loaded with combinations ranging from turkey and roasted peppers to cheese, bacon, and hot sauce (“The Elvis”).
For dessert, Kent is blessed with not one, but two, chocolatiers. At Belgique Pâtisserie, tucked behind a yellow Victorian on the south side of town, the accents are authentic, the espresso expertly drawn, and the café constructs sweets of candied fruits and buttercream that rival anything nature puts on in its annual fall show. It’s finds like these, after all, that epitomize the joy of leaf-peeping in New England—full of color, sure, but also full of surprises.
The Top 25 Foliage Towns in New England | The Magnificent 9
Bethel, Maine
Maine’s mountain gem boasts scenic drives through Evans Notch and a covered-bridge driving tour of the area. On fall weekends, Sunday River Ski Resort’s “chondola” in nearby Newry whisks visitors 1,000 feet up North Peak to the ultimate picnic ground.
Don’t miss: Bethel’s townwide Annual Harvest Fest & “Chowdah” Cookoff, where local restaurants compete for bragging rights.
Manchester, Vermont
The second-highest peak in southern Vermont, Equinox Mountain offers unbroken views stretching miles to the surrounding ranges—a painter’s palette of gold and crimson by the first week of October. In August, the town hosts the annual Southern Vermont Art & Craft Festival, which draws artisans from around the Green Mountains.
Don’t miss: Northshire Bookstore, the independent bookshop/café you might have created in your dreams.
Williamstown, Massachusetts
The ultimate college town, sheltered in the arms of Massachusetts’ highest mountain (Mount Greylock, in nearby Adams), Williamstown’s mix of eclectic architecture and inviting quads can’t help but inspire lofty thoughts. The drive up Mount Greylock affords dizzying views of the Berkshires and the Taconic Range, but the favorite hike for Williams College students is the two-mile pitch up to Pine Cobble, a quartzite outcropping with a panoramic view of “the Purple Valley” and church spires below.
Don’t miss: the stunning Impressionist collections at the Sterling and Francine Clark Art Institute.
Middlebury, Vermont
The 16-mile “Trail Around Middle- bury” provides an ideal walking route where families can soak in the atmosphere of this vibrant college town. Here the fall foliage harmonizes with the brick architecture and the roar- ing falls of Otter Creek, with eclectic shopping and restaurants along the way.
Don’t miss: the A&W Drive-In, where frosty root beers and fried onion rings from one of New England’s last car-hop restaurants perfectly complement the crisp fall air.
Camden, Maine
The view from the forested slopes of Mount Battie straight down to the forest of masts in Camden Harbor is one of the most dramatic in New England—and never more beautiful than in fall. For a closer look at the trees, hike nearby Mount Megunticook or Bald Rock Mountain.
Don’t miss: the crispy cider doughnuts at Boynton-McKay Food Co.
Waitsfield, Vermont
Iconic barns and hillside farmlands carpet this narrow valley between Green Mountain ranges, reflected in the rushing currents of the Mad River. The town has two covered bridges, including the Great Eddy (a.k.a. Big Eddy), the second-oldest operating covered bridge in the state. Saturday mornings bring local residents out for fresh produce, crafts, and music at the weekly Waitsfield Farmers’ Market on the Green.
Don’t miss: the gourmet pizzas at American Flatbread.
Conway/North Conway, New Hampshire
There may be no better way to see foliage than by train; the Conway Scenic Railroad is just the ticket, wending its way through White Mountain clefts and over trestles lit by the colors of fall. Restaurants and outlet shopping ensure that you won’t sacrifice comfort for beauty.
Don’t miss: the hike to Diana’s Baths (off West Side Road on the Bartlett town line), a chain of waterfalls and swimming holes enveloped in foliage.
Sandwich, New Hampshire
Sandwiched between the loon-rich shores of Squam Lake and the forested foothills of the White Mountains, the village offers plenty of hiking trails, driving routes, a covered bridge, and an inviting downtown.
Don’t miss: the 100-year-old Sandwich Fair, with midway rides, livestock competitions, and more.
Rangeley, Maine
The lakes of Maine’s western mountains hold up a succession of mirrors to some of the state’s best fall foliage. The must-stop viewpoint in the area is at a small turnout on Route 17, aptly named Height of Land, from which a panorama of five lakes and count- less forested mountains stretches in all directions.
Don’t miss: the annual Logging Museum Apple Festival, where visitors can press their own cider while watching artisans “whittle” away with chainsaws.
The Top 25 Foliage Towns in New England | The Sweet 15
Blue Hill, Maine
Maine’s blueberry barrens light up red in a display of foliage every bit as gorgeous as anything on the trees. Pick up picnic supplies at a local organic farmstand and admire the reflection of the trees along with the buoys bobbing in the surf.
Don’t miss: the annual Foliage, Food & Wine Festival, a celebration of leaves and local produce.
Woodstock, Vermont
Dairy farms and art galleries share equal space here: a sophisticated cross-roads and Vermont’s quintessential small town. Billings Farm & Museum features wagon rides, food-themed events all season (and year-round), and Jersey cows. With an addictive Main Street for browsing, you’ve got all the ingredients for fall.
Don’t miss: The Prince & The Pauper restaurant, where rustic décor meets a regal menu.
Waterville Valley, New Hampshire
Feng shui doesn’t get any better than the U-shaped mountain range that cradles Waterville Valley; the area is particularly memorable in fall, when the slopes light up in a rainbow of colors, dominated by the steep rises of Tripyramid and Osceola. Ample hiking trails invite outdoor enthusiasts to enjoy the slopes.
Don’t miss: Coyote Grill, where stunning views are served up alongside inventive American cuisine.
Amherst, Massachusetts
Local poet Emily Dickinson knew how to appreciate the subtle beauty of nature—from a certain slant of light to the changing shades of a sugar maple. Now her family homestead is one of the many cultural attractions that come alive each fall when the students return to picturesque Amherst College. The highlight of the season is the annual Fall Foliage Walk from the town common, across campus, and along the tree-lined ridge of the Norwottuck Rail Trail.
Don’t miss: the whimsical illustrations and paintings at The Eric Carle Museum of Picture Book Art.
Grafton, Vermont
Many of the buildings on Grafton’s main street are owned by the Windham Foundation, a private organization that has painstakingly restored its properties into a classic vision of small-town life. The village is particularly charming during fall, when the golden leaves from the towering oaks spread out in a carpet along the path behind the Grafton Village Cheese facility, one of Vermont’s best cheddar producers.
Don’t miss: The Old Tavern, an inn filled with history and antiques, along with an award-winning restaurant that works Grafton cheddar into its dishes.
East Haddam, Connecticut
Water and leaves perform a charming pas de deux here every autumn, from the picturesque reflections in the Connecticut River to the brilliant counterpoint of the cascading brooks and waterfalls of Devil’s Hopyard State Park.
Don’t miss: the medieval whimsy of Gillette Castle, created by an eccentric actor, who also laid hiking trails through tunnels and over stone bridges on the surrounding estate.
Walpole, New Hampshire
When filmmaker Ken Burns went looking for a home, he landed here, a beautiful village with a town green bordered by 19th-century homes and churches, with farms, orchards, and the Connecticut River for close company.
Don’t miss: Alyson’s Orchard. It’s simply one of the best orchards in the country, with a heart-stopping view. Leave room for a stop at L. A. Burdick for world-famous chocolate and exceptional dining.
The Cornwalls, Connecticut
Quieter than Kent, its Litchfield Hills neighbors are latticed with picturesque driving routes through Mohawk State Forest. Take in the view from Cunningham Tower, picnic at Housatonic Meadows State Park in nearby Sharon, or just admire the astounding length of the brick-red West Cornwall Bridge.
Don’t miss: a foliage canoe trip along the Housatonic with Clarke Outdoors.
Litchfield, Connecticut
Litchfield’s flawless, tree-studded town green may just be one of the best picnic spots in the world. It’s surrounded by a profusion of Colonial-era architecture as well as upscale boutiques catering to daytrippers up from the city.
Don’t miss: the town’s half-dozen specialty and organic farmstands—especially the PYOP (pick-your-own-pumpkin) hayrides at Bunnell Farm.
Jackson, New Hampshire
You enter the village through a covered bridge, and once there you may well feel as if there’s no reason to leave. Blanketed by White Mountain National Forest, with hiking paths heading off in all directions, Jackson is the jewel of the Whites. Long known as summer-resort havens, Jackson’s inns are now filled by Nordic skiers throughout the winter. But the region never sparkles more than it does in fall.
Don’t miss: the Jackson Scenic Loop (off Route 16B). Follow the signs from 16B by bike, on foot, or by car, for five miles of stunning mountain scenery.
Jeffersonville, Vermont
The curving climb up through Smugglers’ Notch and alongside the cliffs of Mount Mansfield is one of the best scenic drives in all of New England— and the more so since it ends up in the pretty village of Jeffersonville. It combines views of Smugglers’ Notch Resort, south of town, with plenty of amenities and a cute downtown area filled with galleries and antique shops catering to foliage seekers.
Don’t miss: Bryan Memorial Gallery, Vermont’s primary showcase for landscape art.
Shelburne Falls, Massachusetts
Take an abandoned trolley bridge, plant it with blooming greenery, and voilà! You create a town icon and tourist attraction. But the Bridge of Flowers is just the beginning of the appeal of this stranded-in-time turnoff from the Mohawk Trail, now a haven for artisans, who sell their wares in studios by the falls of the Deerfield River.
Don’t miss: High Ledges Wildlife Sanctuary, a four-mile trail network and scenic picnic area east of town, overlooking the valley.
Montgomery, Vermont
Way up north, not all that far from the Quebec border, Montgomery is a covered-bridge-lover’s paradise, with no fewer than seven within a few miles of the village. This majestic yet remote location keeps most leaf- peepers far away.
Don’t miss: The lovely Inn on Trout River, a real-deal country lodging place filled with antiques and a homey vibe. Stop in for a touring map of the bridges.
Stowe, Vermont
It’s hardly off the beaten track, but then again, there are ample reasons why the bus tours head to Stowe come fall: its Old World town center, its inviting mix of shops and restaurants, its walking and hiking trails head- ing off in all directions.
Don’t miss: Oktoberfest, a lively, authentic Bavarian celebration of foliage, the harvest, sausage, traditional music, and beer—not necessarily in that order, of course.
Hanover, New Hampshire
There’s a reason one of the country’s most famous outing clubs is here, home of Dartmouth College: the lush landscape. If the Connecticut River, the Appalachian Trail, and the nearby mountains don’t put a kick in your step, nothing will. Or, if you just want to relax close to home base, you can easily spend a day in the soft sunlight, people-watching on the college green.
Don’t miss: the Ledyard Canoe Club. Rent a canoe or a kayak from the nation’s oldest boating club, then paddle along the riverbank, soaking up color while discovering why college kids skip their classes to come here.
How We Picked the Top 25 Foliage Towns in New England
Of course, picking the ultimate foliage destination is a subjective experience—and there are as many favorite spots for leaf-peeping as there are residents in New England. In picking the best, we decided to focus on the total foliage “experience”—not just the prettiest leaves.
We began by soliciting nominations from a wide variety of tourism professionals, as well as Yankee’s own writers and editors. Once we had a working list of contenders, we then rated them according to 14 categories: color intensity, scenery, vistas, nearby water, scenic drives, hikes, culture, farmers’ markets and farm- stands, orchards, covered bridges, state or local parks, the quality and variety of shops to browse, tourism amenities such as hotels and restaurants, and a category we call “uncrowded”—giving a boost to those out-of-the-way locations outside the tour-bus scrum.
In every category, we gave each town a score of 0 to 5. Criteria for evaluating some categories were objective. For covered bridges and orchards, for example, our score reflects whether a town is blessed with one or more (high score, 5) or whether they’re within a short drive, all the way down to 0. Other categories, such as scenery and nearby water, were ranked more subjectively. When we totaled the numbers, however, the cream quickly rose to the top—giving us the 25 towns listed in these pages.
