Summary
- Massachusetts is home to charming small towns with stunning fall foliage displays, offering a peaceful alternative to popular tourist destinations.
- Lenox, Stockbridge, and Northampton are among the least-crowded towns in Massachusetts during fall, featuring vibrant autumn scenery and attractions.
- Visitors can enjoy activities such as hiking, exploring historic sites, and taking scenic drives to appreciate the beautiful fall colors in these off-the-beaten-path Massachusetts towns.
One of the most incredible things to do in New England in the fall is to explore its small towns. In particular, Massachusetts is home to many of them and is a state famous for its stunning fall foliage displays that attract visitors from all over. Starting in late September and lasting through October, the state explodes into a kaleidoscope of vibrant red, orange, and yellow leaves that carpet the countryside. That's why, every year, one of the best things to do in Massachusetts in the fall is to go leaf-peeping.
While popular destinations like Cape Cod and Boston see a surge of leaf peepers during this time, there are many charming, lesser-known towns in Massachusetts that offer spectacular autumn scenery without the crowds. These off-the-beaten-path destinations deliver the same jaw-dropping views of fall foliage that the state is renowned for but with a fraction of the tourists.
From quaint rural villages to historic mill towns set along rivers and ponds, these overlooked spots showcase the distinct charm and natural beauty of New England in the fall. For travelers looking to take in the dazzling autumn colors this season in a more peaceful setting, here are some of the least-crowded towns in Massachusetts in the fall.
10 Lenox
Nestled in the heart of the Berkshires (where leaf-peepers can find some of the most scenic fall hikes in Massachusetts), Lenox is a charming small town that delivers spectacular autumn scenery without the crowds. Its quaint main street, lined with historic homes and cozy cafés, comes alive with vivid red and orange foliage. Travelers can take a peaceful stroll down Church Street to Pleasant Valley Sanctuary, where the colorful changing leaves canopy hiking trails.
Visitors shouldn't miss Kennedy Park in the center of town, where they can spread out a blanket under a backdrop of fall brilliance and take in the views.
- Hours: Kennedy Park is open daily from sunrise to sunset. Ventfort Hall is open Thu-Mon, 11 a.m.–4 p.m.
- Best Time to Visit: Late September to mid-October for peak foliage.
- Top Attractions: Tanglewood, Ventfort Hall, Gilded Age Museum, Pleasant Valley Wildlife Sanctuary
9 Stockbridge
Adjacent to Lenox, Stockbridge also provides a peaceful fall getaway in the Berkshires. Visitors can stroll down its iconic Main Street, lined with shops, restaurants, and the famous Red Lion Inn, all surrounded by blazing maples and oaks overhead.
Travelers can also visit the Norman Rockwell Museum to find inspiration behind the artist's iconic fall-themed paintings. Or hike the grounds of Naumkeag, an elegant Gilded-Age estate with gardens that transform into a kaleidoscope of autumn hues.
- Things to Do: Hike Monument Mountain (3.5-mile loop, moderate difficulty) and visit Naumkeag Gardens.
- Tour Duration: 2–3 days to explore the town.
8 Northampton
Northampton is another one of the uncrowded towns in Massachusetts in the fall, but it still comes alive in autumn with its vibrant mix of art galleries, shops, restaurants, and Smith College's stunning "Elm Tree" lined campus.
For panoramic views of the entire Connecticut River valley painted in an array of fall colors, visitors can hike to the top of Mt. Tom. Or stroll across the historic Pine Street bridge overlooking the foliage reflected in the river's calm waters. Travelers also shouldn't miss Paradise Pond, a tranquil spot perfect for an autumn picnic surrounded by the season's palette.
- Top Attractions: Smith College Museum of Art, Thornes Marketplace, Look Park
- Tour Duration: A long weekend would allow enough time to explore Northampton's sights.
- Best Time to Visit: September to October for foliage and fall activities.
7 Amherst
Home to Amherst College, this youthful college town has inviting cafes, boutiques, and bookstores that make leisurely strolls in the crisp fall air a pleasure for visitors. Travelers can rent a bike and ride along the Norwottuck Rail Trail, taking in the patchwork of autumn hues along the way.
They can also stop at the Emily Dickinson Museum to learn about one of Amherst's most famous former residents. Or pop into the Mead Art Museum on campus for some indoor cultural appreciation.
- Things to Do: Hike the Robert Frost Trail (easy 1.2-mile loop), visit the Emily Dickinson Museum, Amherst College campus tour
- Top Attractions: Emily Dickinson Museum, Mead Art Museum, Eric Carle Museum of Picture Book Art
6 Hadley
In the heart of the Pioneer Valley, Hadley is one of New England's least-crowded towns in the fall, with farms, orchards, and the Mount Holyoke Range awash in autumn colors. Visitors can take a scenic drive along Route 47 to view pastures and woodlands vibrant with autumn foliage. Lake Warner is also great for fishing and quiet walks surrounded by nature's fall finery.
Travelers should take advantage of hiking to the summit of Mount Norwottuck on the Holyoke Range for panoramic outlooks over the blazing treetops.
- Hike Length: Mount Norwottuck via Horse Caves Trail is a 5.4-mile roundtrip
- Difficulty: Moderate due to steep inclines
- Things to Do: Lake Warner boating/fishing, tour Hadley Farm Museum, Holyoke Range State Park, hiking
5 Westfield
Westfield's historic downtown, lined with shops, restaurants, and antique stores, provides small-town appeal, while the adjacent Columbia Greenway Rail Trail that borders the Westfield River makes for the perfect spot for travelers to take a fall foliage stroll. Visitors can find a peaceful riverside perch to watch the leaves reflecting along the water amid tranquil natural surroundings.
Westfield's Stanley Park also draws leaf peepers with its many tree varieties, creating a vibrant autumn display.
- Things to Do: Westfield River Boat Tours, Westfield Athenaeum Museum, Stanley Park walking trails
- Top Attractions: Noble and Cooley Drum Factory Tour, Columbia Greenway Rail Trail
4 Easthampton
Easthampton's parks, trails, and views of the Mount Tom Range paint an incredible fall scene for visitors. Travelers can stroll around Lower Mill Pond in the town center to take in the foliage brilliantly reflected in the calm waters. Or hike to the top of Mount Tom for panoramic outlooks over the entire Pioneer Valley countryside swathed in autumn's palette.
Nashawannuck Pond is another popular locale surrounded by fiery fall hues.
- Top Attractions: Mount Tom State Reservation, Arcadia Wildlife Sanctuary, Nashawannuck Pond
- Things to Do: Bike the Manhan Rail Trail, Oxbow Marina kayaking tours
- Best Time to Visit: September to mid-October for peak foliage viewing.
3 Greenfield
Greenfield's historic Main Street, lined with shops, cafes, and restaurants, provides quaint small-town charm, while the Green River's blazing waterfront makes a picturesque spot for fall reflection views. Visitors can make the short hike up Poet's Seat Tower for panoramic vistas over the surrounding hillsides ablaze with autumn color.
The area's covered bridges spanning the Deerfield River also make for scenic photo options surrounded by fall's brilliance.
- Things to Do: Historic Deerfield village tours, hiking Poet's Seat Tower, Freeman's Flyer canopy zip line tours
- Top Attractions: Shelburne Falls, the area's scenic covered bridges
2 Ashfield
Ashfield is another one of the less-crowded towns in Massachusetts in the fall; its rural landscape, dotted with farms, historic homes, valleys, and rolling hills, makes it a quintessential New England destination for travelers to immerse themselves in autumn's charm away from tourist hotspots.
Visitors can take a scenic drive along the Mohawk Trail (which is one of the many beautiful New England road trips for fall), stopping frequently to photograph the foliage against the backdrop of blue hills. Walk across the narrow Beach Hill Bridge over the fall-transformed Mill River. And stroll through the Ashfield Fall Festival to shop, dine, and take in community spirit.
- Festival Dates: Columbus Day weekend
- Amenities: Ashfield Lake campground, country B&Bs
- Things to Do: Hike up to Poet's Seat Tower, tour Bear Swamp Apple Orchard & Bakery
- Top Attractions: Ashfield Fall Festival, scenic Mohawk Trail (Route 2)
1 Williamstown
Williamstown delivers a trifecta of natural splendor, small-town New England charm, and cultural attractions in northwest Massachusetts. Travelers can hike up Mount Greylock for bird's eye panoramic views over the entire countryside swathed in autumn's flaming foliage.
Visitors can also stroll Williams College's campus, where the grassy quads and surrounding trees explode into seasonal color. The Clark Art Institute's grounds and hiking trails highlight nature's fall brilliance for art and nature lovers alike.
- Top Attractions: Clark Art Institute, Williams College Museum of Art, Mt Greylock summit
- Things to Do: Hike Mount Greylock and tour the Williams College campus.
- Best Time to Visit: September-October for foliage.