Small Towns In New England That Come Alive In The Fall
As the weather cools and sunshine dwindles, New England's charming towns offer a vibrant autumn experience. These eleven towns shine during fall, with crisp weather enhancing their appeal.
New England is worth visiting every season, but its fall foliage stands out. With lively towns like the Berkshires and attractions in Acadia National Park, the region truly celebrates the autumn season.
Bar Harbor, Maine
Bar Harbor, on the northeastern side of Mount Desert Island, is easily the most enticingly remote destination in New England. It is not surprising that the small town stays lively in the fall following summer crowds—not after you catch the fiery foliage reflecting in the harbor. The town's original name, Eden, complementing the paradise-like surroundings, starts making sense as a generations-beloved unofficial gateway to the pristine mountains, cliffs, and forests of the waterfront Acadia National Park.
A kayak or stand-up paddleboard into Frenchman Bay offers the best views of the dancing treeline along Mount Desert Island’s coastline, where you can even debark for a picnic with your peeps. The Beehive Loop, just 10 minutes away, is an arduous 1.5-mile hike with steep sections of granite staircases and exposed iron-rung ladders to the expansive, photoshoot-worthy views of the contrasting foliage against the sea. Acadia National Park has 45 miles of designated, car-free carriage roads for cyclists that crush through the colorful woodlands, and you can even rent a bike on the island. In between peepings, a lobster roll is always in season for a quick bite to recharge anytime in Bar Harbor.
Bristol, Rhode Island
A town unlike any other when it comes to putting on a falltime spectacle in the state, it is one of Rhode Island's cutest and among the less crowded ones in New England to greedily peep through the fall foliage. Flying just under the radar, the lovely Colt State Park is the best place for excellent foliage strolls or hiking. Next up, the Blithewold Mansion’s Gardens and Arboretum, all dressed up for the season, offer an only-here experience just past the iconic Blithewold Mansion, off Ferry Road, designed in the style of an English Country Manor.
Bristol's Gardens & Arboretum greets with a heady scent of roses, delighting all in the too-late season for blooms. While not the typical fall foliage mission stop, the mansion soon to be opened for touring the decked-out holiday interior fits the fall scenery with a festive spirit on your autumn getaway in Rhode Island. The grounds, with a lush lawn and various rare trees along a walking path, are a blissful burst of colors and pure serenity on a stroll. You can explore along the tree-lined streets of the small town with little restaurants to warm up over an authentic New England hearty portion of a creamy Clam Chowder or French Onion soup.
Great Barrington, Massachusetts
Great Barrington is always "in season" for a fun visit, steps away from some of the best nature in New England. With the promise of the stunning Berkshires, the state's most sought-after peaks, the small town in the shadow is a pretty sight year-round but is downright magnificent under the stunning fall views of the Berkshires. A hike up the town's totem, Monument Mountain, with Housatonic River Valley views from the summit and soaring eagles around makes a pretty hefty dent in the state's top foliage pursuits.
With plentiful available cabins and lovely vacation rentals, you can stay cozy near all the best trails to explore the foothills and along the Housatonic River on a stroll with a brewery scene and Aegean Breeze Restaurant, a local favorite, to recharge after. The 1,642-foot Peeksakawso Peak beckons over 20,000 adventurous hikers a year. Written by the famous American poet William Cullen Bryant in his eponymous poem in 1815, it must have been after experiencing the hike through the foliage to the peak.
Jefferson, New Hampshire
Jefferson's nature wakes the sleepy town up in the fall—a real golden nugget of New Hampshire. Ensconced in the grandeur of the White Mountains in the northern portion of the state, Jefferson sits quintessentially surrounded by farms and forests—a real paradise for fresh air and incredible scenery. Whether you're more of a play-a-round kind of person at none other than the state's oldest 18-hole golf course or a foliage hunter through the remarkably beautiful Pondicherry Wildlife Refuge.
The town is just getting started with some out-of-this-world foliage for your hiking pleasures and quiet paddles along local lakes and rivers, which will soon be covered up in a white blanket. The endless miles of trails through colors along your path and the panoramic views of the Presidential Mountains covered in foliage with nearby farms await family visits with more open views and so much air between farmlands and the White Mountains.
Kennebunkport, Maine
This famous town, sought out by summertime boaters, finally receives a respite starting in the fall, with most sailors back at work. Now is the time to visit Kennebunkport for canoeing adventurers or rent a kayak to explore the waterways lushly decorated in various colors along the Kennebunk River. The idyllic town welcomes lucky fall time vacationers after a captivating drive through the enchanting highway-lined lush forests into its own red and yellow foliage beauty along the streets.
With Colony Beach, Gooch’s Beach, and Mother’s Beach at your disposal, you can stroll the rugged shoreline and lounge at the views of the navy blue waters, beautifully reflecting the cloudy gray skies and foliage along the banks. Steer clear of the water splashes and soak in the mesmerizing colors of the fall with some of the region's best hikes or a bike ride along the tree-lined Eastern Trail.
Lenox, Massachusetts
Lenox, another Berkshire County darling town, some 20 minutes from Great Barrington, really puts on a show during the fall. With tons of sights and experiences, Mother Nature doesn't wait long after the summer crowds depart to decorate Lenox's year-round natural attraction, Pleasant Valley Wildlife Sanctuary, with vibrant colors for a stroll on a breezy autumn day. The challenging 3-mile round-trip Trail of Ledges/Overbrook Loop Trail, with a 2,126-foot elevation gain, will keep the hikers warm.
Seek more of what you crave along the awe-inspiring rolling slopes of Lenox Mountain through over 1,000 acres of forest, wetlands, and meadows. Families enjoy looping the Pike's Pond Trail in under 1 mile of scenery around the pond, especially at dusk when the beavers come out. These adorable critters put on a real fall time spectacle of playing and preparing for the winter.
Manchester, Vermont
Manchester a laidback mountain town in the southern shadow of Vermont's Green Mountain range is abuzz with breweries, foodie restaurants, art galleries, and many other attractions for toasty fall days. Accessible from Boston and New York City, Manchester delights city dwellers with marble sidewalks and charming covered bridges that fit the fall scenery, while the slower pace and friendly locals lend a comfortable, go-with-the-flow atmosphere.
Hildene, the summer residence built in 1905, just five minutes outside of Manchester, is the best place to see the foliage. This former vacation home of Abraham Lincoln's only surviving child, who became the president of the Pullman Company, is a Georgian Revival mansion on a high hill over the breathtaking scenery of the ever-changing colors through the fall along the sweeping valley and the colorful mountains. The Skyline Drive is the country's longest privately owned, paved toll road, just south of Manchester, with a 3,248-foot ascent over five miles to the top of Mount Equinox.
Mystic, Connecticut
Mystic is one of the best towns to visit in New England for the ultimate falltime combo, with something for everyone to get hyped about. From the foliage to the festivities that climax in October and other fun fall-related experiences, the seaport town is unbeatable in the entertainment department of the state. The Witch Paddle on Mystic River delights the young and the old when over a dozen "witches" appear to fly down the river through the dazzling colors along the banks.
Attracting fleets of tourists with a Halloween-themed name, Mystic exudes New England charm through the stunning change of fall hues—a real magical sight. Travelers can soak up the beautiful sights and sounds of fall on a hike through the 350-acre Denison Pequotsepos Nature Center. The earthy smells of the fallen leaves and glowing atmosphere along the ten-plus miles of trails include the sounds of some 175 bird species.
North Conway, New Hampshire
North Conway, in the heart of the White Mountains, is a voter's favorite among America's best small towns. The quaint mountain town with a great park system and restaurant scene is an ideal fall peeping destination that transitions into a hotbed for skiers. The town surrounded by parks, is a popular autumn getaway, both budget-friendly and naturally abundant. From the end of September through October, the forested foothills of White Mountain National Forest are alight with red spruce, eastern hemlock, beech, and red maple. You can enjoy hikes and scenic drives, with Kancamagus Highway taking the cake as one of New England's prettiest.
The "Kanc" is a 35-mile highway from Conway to Lincoln, designated as an American Scenic Byway, driving through the White Mountains along the Swift River, Sabbaday Falls, Lower Falls, and Rocky Gorge. The natural beauty along the highway feels like a painting with no restaurants, hotels, or even gas stations! Conway Scenic Railroad, built in 1872, is a must-take excursion via two short train rides and the iconic 50–60-mile mountaineer ride through foliage along Mount Washington Valley.
Provincetown, Massachusetts
Cape Cod, perhaps the first area that springs to mind when talking about the New England state of Massachusetts, stays popular year-round, thanks to the lovely sea views and second-to-none autumn foliage. With a slew of small towns, Provincetown, just north of Truro, is one of the most famous yet remote, set along the Outer Cape of the peninsula. Home to just 3,600, blows up to 60,000 in the peak summer season. The historical little village is the real home to Thanksgiving, with the Pilgrims debarking the Mayflower here first, celebrated today with the annual lighting of the Pilgrim Monument on November 11. This largest all-granite building, perched on the top of High Pole Hill Rd., lights up with 3,100 individual lights, shining until January 6.
Renowned for its easy-going atmosphere and edgy vibe, P-town, as the locals affectionately call it, is a year-round destination that transforms into an autumn paradise with the earthy scent of fallen leaves along the streets. Home to a large LGBTQ+ population, it attracts the open-minded with one of the liveliest bar and restaurant scenes on the East Coast. With ferry access from Boston, you can also cross over the Sagamore Bridge for a drive through the whole Cape to experience all the fall flavors through farmers’ markets and festivals.
Williamstown, Massachusetts
With three million acres forested in the state, the Berkshires are the epicenter for fall peeking. This Berkshire County town features the typical woody surroundings that come "on fire" in the fall. This particular jewel of the state, one of New England's best-kept secrets, reigns with cozy falltime scenic pursuits and the lively atmosphere at one of the oldest colleges in the country. With grounds adorned in foliage and the world-class Clark Art Institute, you can enjoy a whole patchwork of natural and cultural falltime wonders.
The Mohawk Trail, the first scenic road in New England since October 1914, stretches for 63 miles of foliage splendor, winding to Greenfield. It runs along 50,000 acres of state parks and forests, with access to the Massachusetts Museum of Contemporary Art (MASS MoCA) and Tannery Falls—some pretty fall-worthy stops for every taste. At the Hairpin Turn, the trail sharply rises to the Western Summit, with an unreplicable panorama for the arduous.
The Takeaway
New England trades the beach scene for apple cider, pumpkin picking', and fall foliage on hikes with no humidity or annoying bugs of the summer. With easy access from the eastern portion of the state, the seaside towns and mountain enclaves won't wait long, with scenery changing as you read these lines.
From scenic drives to hikes and other cozy falltime activities in between, like harvest markets and festivals, celebrate the season of giving thanks in your favorite New England way or even in the town where Thanksgiving was born!
