Outdoor Recreation

Favorite Fall Foliage Hikes

Fall is the best season to hike and view the fall foliage displays. Find prime leaf peeping across the state.

Bear Swamp

Looking to find the best fall foliage hikes in Massachusetts? Autumn is the best season to get outdoors and take in the brilliant leaf displays that New England is known for. We asked our Stewardship Team for their favorite Trustees properties to hike and view the world-famous leaf peeping opportunities. You will be delighted by their list of some of these lesser-known gems.

Appleton Farms,  Ipswich, MA

Six miles of footpaths, bridle paths, and farm roads (easy walking and great for jogging strollers), some of which are part of the Bay Circuit Trail, crisscross this scenic farm.

Fruitlands Museum, Harvard, MA

Fruitlands Museum has a diverse collection of art and material culture on 210 acres of land, stunning views, and miles of walking trails.

Monument Mountain, Great Barrington, MA

Three trails—all under three miles—offer scenic ways for you to get acquainted with the mountain’s pale quartzite geology and wondrous views out to Mount Greylock and the Catskill Mountains.

Rocky Woods,  Medfield, MA

With six and a half miles of trails winding through 491 acres of varied terrain, Rocky Woods is a year-round destination for outdoor lovers and a prized habitat for songbirds, bullfrogs, beavers, and painted turtles.

Ward Reservation,  Andover, MA

Explore this sprawling landscape along almost 15 miles of trails and climb a hill for great views from the Merrimack Valley toward the Boston skyline.

Bear Swamp,  Ashfield, MA

Hike three miles of trails to a nearby beaver pond and discover terrific views of hillside orchards spreading below, along with the distant Green Mountains.

Bryant Homestead, Cummington, MA

Wander the Rivulet Trail, where an old-growth forest of hemlock and a magnificent cherry tree hugs the Rivulet, a trickling stream immortalized by Bryant’s 1823 poem of the same name. The Pine Loop features enormous pines that reach heights of 150 feet, among the tallest in the Northeast.

Copicut Woods, Fall River, MA

With upland forests and remnants of a vibrant agricultural past, the gateway to the 13,600-acre Southeastern Massachusetts Bioreserve is a destination to remember.

Menemsha Hills, Chilmark, MA

Experience fall with a beautiful coastal hike! Hike three miles of trails past holly, high-bush blueberry, and more than a few boulders and glacial erratics. Follow the Harris Trail to the top of the hill, which affords spectacular views of the Menemsha harbor entrance, the Elizabeth Islands, and Gay Head Light. Descend through the woodlands and hardy seaside groundcover to coastal bluffs overlooking Vineyard Sound—possibly one of the quietest seaside landscapes on the island—and enjoy the view or cast a line.

Noon Hill, Medfield, MA

Four and a half miles of moderate (and occasionally strenuous) trails wind around Noon Hill, a link in the Bay Circuit Trail. From the hill’s peak, you’ll be rewarded with sweeping views south across the rolling hills of Walpole and Norfolk, including Gillette Stadium.

Norris Reservation, Norwell, MA

Hike past a former mill pond, cross a wetlands boardwalk, and explore a forest of pine and oak on your way to a boathouse on the banks of the tidal North River.

Peaked Mountain, Monson, MA

The ascent from the main entrance to the summit of Peaked (pronounced “pea-kid”) Mountain is a workout, a climb along a trail that is strenuous in places and gains 467 feet in elevation. But once you reach the top, the 1,227-foot summit provides spectacular views of undisturbed rural and forested landscapes in every direction: a sweep of rolling New England countryside with valley farms and small villages, mountains, hills, and even the distant city of Springfield.

Ravenswood Park, Gloucester, MA

Ten miles of woodland paths and trails meander through the park, providing plenty of room to picnic, bird watch, walk,  and simply appreciate the outdoors. Wander the child-friendly, two-mile Ledge Hill Trail among the magical-looking, fern-covered boulders, or trek to the overlook to Gloucester Harbor.

Rock House Reservation, West Brookfield, MA

Discover the nooks and crannies of this 296-acre tract via three miles of trails and woods roads. The centerpiece is the 20-to-30-foot-high rock enclosure that stands guard over man-made Carter Pond. Along the way, savor the wildflowers, hardwood forests, and pine groves, and watch for a wide variety of animals, from wild turkeys to painted turtles.

​Swift River Reservation, Petersham, MA

With majestic old pine and hemlock lining its banks, Swift River is one of the most scenic trout streams in the Commonwealth and a favorite for sport fishermen. Varied topography and flora support an abundance of wildlife, including deer, beaver, raccoon, porcupine, bear, bobcat, and coyote as well as numerous songbirds, owls, and birds of prey.

Tyringham Cobble, Tyringham, MA

Hike two miles of trails—including a section of the Appalachian Trail—over the twin knobs of the Cobble for spectacular views of the valley. Keep an eye out for an unusually shaped rock formation known as Rabbit Rock. Hop Brook, a favorite fishing stream of President Grover Cleveland, meanders along the northern edge of the reservation on its way west to the Housatonic River.

More places see changing leaves