Fall in New England is known for a few things. Apple picking, some of the best apple cider and donuts around, crisp weather perfect for soaking up the last few days of longer light, and of course, the autumn leaves. Fall foliage in New England transforms tree-covered hills, mountains, and valleys into stunning arrays of warm reds, oranges, and yellows.
The Trustees is proud to steward some of the best special places for fall leaf-peeping. No matter where you are in Massachusetts, we have a property that will welcome you with stunning seasonal scenery. From Menemsha Hills on Martha’s Vineyard to Peaked Mountain in Monson, and many places in between. We’ve rounded up a few of our favorites, including properties with guided hikes this fall season, many with partner Adventure East.
Appleton Farms in Ipswich
North Shore
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. In the fall, the farm comes alive with the harvest, and not only holds fun seasonal events, but is a fantastic spot to find yourself amongst the changing scenery.
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. The wide diversity of ecological habitats at Ward make it a special place, especially as the seasons change. 420-foot Holt Hill, the highest point in Essex County, is perfect for sweeping views of fall’s brightest colors.
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 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. Ravenswood immerses you in a forest full of change in the fall, making it another favorite for the season.
Copicut Woods in Fall River
Southeast, Cape & Islands
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. While you’re enjoying the property, be sure to check out the recently opened Discovery Trail.
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.
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. Fall and football – what a perfect fit!
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. This waterside hike offers an experience that makes fall in New England so special, experiencing the changing colors by the coast.
Powisset Farm in Dover
Metro-West
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.
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. The vista of the Nashua River Valley is stunning – don’t miss the scenic overlook.
Explore the loop trail on this local treasure and vibrant working farm, taking in the surrounding woodlands, fields, and wetlands. Fall on the farm is truly magical, as farmers work to bring in the harvest, and prepare the land for winter, while nature changes all around. Don’t miss some of the fun programming happening on the farm while you’re there!
Peaked Mountain in Monson
Central Mass & The Valley
The ascent to the summit of Peaked Mountain is a workout, a climb along a trail that gains 467 feet in elevation. Once you reach the top, the 1,227-foot summit provides spectacular views of undisturbed rural and forested landscapes in every direction: rolling New England countryside with valley farms and small villages, mountains, hills, all awash with the colors of the season.
Adventure East leads a Fall Foliage Hike at Peaked Mountain on Sunday, October 24. Find out more here.
Chesterfield Gorge, Chesterfield, MA
Hike the half-mile trail along the cliff tops and take in wonderful views of the gorge, the river, and the surrounding forest. The forest nurtures hemlock, ash, and oak, and is home to bears, bobcats, and turkeys (fitting for the season).
Adventure East leads a Fall Foliage Hike at Chesterfield Gorge on Saturday, October 12. Find out more here.
Mount Warner, North Hadley, MA
Old cart paths and woods roads reveal the farming and logging past of this sloping woodland. Mount Warner stands amid a 500-acre swath of protected land linking nearby Lake Warner to a range of conservation treasures and making it the perfect place to take in the beauties of nature during autumn.
Adventure East leads a Fall Foliage Hike at Mount Warner on Monday, October 14. Find out more here.
Bullitt Reservation, Ashfield and Conway
Bullitt is a blend of fields and farm buildings, mixed woodlands, and streams that form a crucial link in almost 3,000 acres of protected land that shelters state-protected species.
Take an easy amble along the Pebble Trail, or if you’re up for a longer trek, the Two Bridges Trail connects to Chapel Brook Reservation, then into a larger network of footpaths in Ashfield and into the broader Pioneer Valley.
Adventure East leads a Fall Foliage Hike at Mount Warner on Sunday, October 6. Find out more here.
Monument Mountain in Great Barrington; photo by Richard Cheek
Western Hills & Berkshires
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.
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.
