The Best Places to See Fall Colors in Massachusetts

Autumn in the Berkshires region of Massachusetts
DenisTangneyJr / Getty Images

With each cold autumn night, foliage colors come alive across Massachusetts' diverse terrain. From the mountains of the Berkshires to the tip of Cape Cod and even on the islands of Nantucket and Martha's Vineyard, fall colors intensify with each passing day beginning in late September. How long the show will last is anyone's guess. In the higher altitudes and in the northern part of Massachusetts, peak color often coincides with the second Monday in October. In coastal areas and in downtown Boston, hints of color can linger well into November. 

Even as leaves swirl to the ground, Massachusetts is a place where every scenic drive and every fall hike seems to lead deep into a story of America's past. Seek out these ultimate places to view colorful leaves, and you'll also sense the spirit of those who have cherished and protected these landscapes for centuries.

01 of 08

Mount Greylock

farmhouse with a mountain forest in the background with fall foliage
DenisTangneyJr / Getty Images
Mount Greylock, Adams, MA 01220, USA

One of the best and easiest summit drives in New England awaits in the Berkshires. Massachusetts' highest peak was already the stuff of legends before J.K. Rowling noted that Mount Greylock is home to North America's school of wizardry. It is said that Herman Melville looked out at the mountain's hulking shape from his study at Arrowhead and saw the great white whale he gave eternal life in "Moby Dick." The true magic here is the dusting of fall color that Mother Nature sprinkles on the 12,500 acres of dense forest you will see when you climb the 92-foot Veterans War Memorial Tower on the mountaintop. Make reservations in advance to enjoy dinner with a view of the fall colors from Bascom Lodge, the magnificent stone summit house built here in the 1930s by the Civilian Conservation Corps.

02 of 08

Mohawk Trail

aeiral view of a hairpin turn through a yellow and green forest
haveseen / Getty Images

It's better to be a passenger than the driver along Massachusetts Route 2, aka the Mohawk Trail, in the rugged northern Berkshires. Your car windows will frame breathtaking views of autumnal hues emerging on treed hillsides and in the sweeping valleys below, but if you're behind the wheel, you'll want to focus on the twists in the road, especially the famous hairpin turn. Officially named a scenic tourist route in 1914 by the Massachusetts legislature, New England's oldest scenic drive actually traces a path first blazed by this region's Native American warriors and traders. In the 33 miles between Williamstown and Shelburne Falls, the most scenic stretch of Route 2, there are plenty of attractions worth visiting: art museums, natural wonders, restaurants with views. The one must-see is the Bridge of Flowers in Shelburne Falls, which blooms in harmony with its autumn surroundings.

03 of 08

William Cullen Bryant Homestead | Cummington, Massachusetts

William Cullen Bryant Homestead in the Fall
Kim Knox Beckius
207 Bryant Rd, Cummington, MA 01026-9639, USA
Phone +1 413-532-1631

It was not Massachusetts-born poet William Cullen Bryant who called autumn "the year's last, loveliest smile." It was actually his little brother, John Howard Bryant, who must surely cringe in the afterlife each time his beautiful words are misattributed. For those of us alive to wander the 195-acre homestead that was childhood home to the Bryants, what matters is that its old-growth forest, fields, and stream still have the power to inspire creativity. The estate, now owned by the Trustees of Reservations and open free to the public, is at its loveliest in the fall, when centuries-old maples flame with autumn's orange and gold. Bring your notebook, camera, or easel, sit on an old stone wall, and try to capture the homestead's beauty

04 of 08

Historic Deerfield

18th-century house with trees in the foreground and leaves on the ground

De Agostini / G. Sioen / Getty Images

80 Old Main St, Deerfield, MA 01342, USA
Phone +1 413-774-5581

As trees trade their green for glittery fall shades, you won't find a prettier street to stroll than Deerfield's Main Street, where Historic Deerfield preserves a dozen antique homes, dating from 1730 to 1850. Wander in and out of the charming abodes, keeping in mind that "The Street" itself is Deerfield's oldest artifact. It was laid out by surveyors in the 1670s following a route used by the native Pocumtucks. Dining in the cozy environs of Champney's at the Deerfield Inn is a fall tradition. So is a drive 5 miles south on Route 5 to Yankee Candle Village to bring home the scents of fall.

Continue to 5 of 8 below.
05 of 08

Mount Sugarloaf State Reservation

view of small massachusetts town and highway going over a river with some orange and red trees
Shobeir Ansari / Getty Images
300 Sugarloaf St, South Deerfield, MA 01373-1122, USA
Phone +1 413-665-2928

Leaf-peeping is a spectator sport atop South Sugarloaf Mountain, a 652-foot bump in the central Massachusetts landscape. Until mid-October, the Mount Sugarloaf State Reservation summit road is open to cars, and you can head to the top with binoculars, chairs, and picnic food. Stake out your spot or climb the stone observation tower for 360-degree views worthy of applause. You'll be looking out over an elbow of the Connecticut River, flanked by bright trees, cute towns, and farms. Both before and after the road closes to traffic, hiking up the mountain is an option.

06 of 08

Walden Pond

A fall sunset at Walden Pond in Concord, Massachusetts
Vath. Sok / Getty Images
Walden Pond, Concord, MA 01742, USA

History and scenery converge at Walden Pond State Reservation, where fall leaves reflect in the 62-acre pond most students of American literature know well. It was here in 1845 that, Henry David Thoreau began two years and two months of seclusion in a pondside cabin of his own construction. This exercise in self-sufficiency provided the fodder for Thoreau's book, "Walden," which is widely credited as giving rise to the conservation movement in America. Stroll the path along the shore. If fall weather stays warm, some visitors even wade in at the beach. There is also a boat ramp if you'd like to bring your kayak or canoe for a paddle on this iconic pool. There are so many landmark attractions in Concord, you may want to extend your fall-season stay. Places rooted in American history—like the Old North Bridge, the battlegrounds at Minuteman National Historical Park, the Old Manse, and Sleepy Hollow Cemetery, where Thoreau rests near Nathaniel Hawthorne and Ralph Waldo Emerson on Author's Ridge—are all at their most photogenic in the fall.

07 of 08

Blue Hills Reservation

695 Hillside St, Milton, MA 02186, USA
Phone +1 617-698-1802

So close to Boston, and yet a foliage seeker's dream, the 7,000-acre Blue Hills Reservation has 125 miles of trails for hikers of every ability. For city dwellers who don't own or have access to a car, this natural expanse is even accessible via public transportation, although it's a bit of an adventure via the T—Boston's subway—to Ashmont Station, where you can connect with the Mattapan High-Speed Line then a local bus to the Blue Hills Trailside Museum. From there, you can follow the mile-long, moderately steep, red-dot-marked trail to the top of Great Blue Hill. From Eliot Tower at the summit, you'll see a fall-colored carpet of trees and the Boston skyline. You might even spy New Hampshire's Mount Monadnock on a clear day.

08 of 08

Cranberry Country

Floating Cranberries in Carver Massachusetts
KenWiedemann / Getty Images

Trees aren't the only source of fall color in this major cranberry-producing state. Nothing is quite as stunning as a cranberry bog during harvest season, when these ruby-red beads are flooded to the surface for scooping. The cranberry-growing industry is centered around Carver, Massachusetts, though the growing region stretches to Cape Cod. From the last week of September until late October or even into November, you can see brilliant foliage and ripened berries at some of these bogs that welcome visitors.   

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The Best Places to See Fall Colors in Massachusetts