Autumn Escapes: Easy Day Trips, Lasting Memories

There’s nothing quite like a fall day in New England. The array of colors dotting the trees as leaves change, a crisp breeze, and a fleeting feeling before winter sweeps in and transforms the landscape.

Turn a fall visit into a moment you won’t soon forget by making a day of it! There are Trustees day trips to take across the state, offering multiple perspectives of our unique and special places. Whether you’re heading out with your young family, making the most of your retirement, looking to learn, or enjoying a solo adventure, consider these day trip possibilities.

For the Family: Farms, Forests, and Adventure on the South Shore

World’s End, Weir River Farm, and Whitney and Thayer Woods

Spend a day in Hingham, visiting World’s End, Weir River Farm, and Whitney and Thayer Woods. These three properties in close proximity to each other offer a wide array of family fun from farm encounters to seaside hikes and walks in the woods. 

Start your day at World’s End. Take advantage of early morning energy as you hike up the drumlins for scenic views of Hingham Harbor and the Boston skyline. While you walk, keep your eyes peeled for wildlife—from deer and turkeys to songbirds and sea creatures. 

Next, venture to 75-acre Weir River Farm, just ten minutes away. Take in a new perspective of Boston from atop the hill before meandering down from the parking lot on Turkey Hill Lane and visiting the friendly sheep, goats, and chickens who call this working farm home. During the fall, the barnyard is host to a variety of seasonal programming. From weekly offerings like barnyard story hours, to Farm Explorers and Boo in the Barnyard, all ages can find something to enjoy.

Just across the street is Whitney and Thayer Woods. The varied terrain on the woodland trails offers the perfect moderate challenge for families with older children, or those looking to take a more adventurous route. Take one of many routes along 10 miles of carriage roads through forests and into open fields and catch stunning views of Boston and the South Shore along the way. 

For the Active Adult: Adventure on the Trail in South Central Massachusetts

Peaked Mountain, Tantiusques, and Quinebaug Woods

Peaked Mountain, Tantiusques, and Quinebaug Woods offer a hearty challenge—and not just in pronouncing their names! Visit the southern border of Massachusetts to enjoy an active fall day. 

Peaked Mountain in Monson is a must-visit Trustees property, especially for those looking for a workout with a view. The sometimes-strenuous trail gains 467 feet in elevation, leading to the 1,227-foot summit. The views from the top astound—with sweeping vistas of New England countryside, made even more beautiful in fall months as the leaves change. 

If you’re looking for a less strenuous but equally rewarding walk, enjoy another portion of the property that traverses the Miller Brook Tract. Choose from multiple short loop trails. Spot the Lunden Pond Dam, which will be removed in the coming years to improve aquatic connectivity and resiliency at Peaked Mountain—making a case for a great return trip in the future to see how the landscape changes. Try to catch glimpses of beavers, herons, and other wildlife drawn to the water.  

Tantiusques in Sturbridge is the site of one of the oldest mines in New England, first stewarded by the Nipmuc people. Take the Leadmine Loop trail through forests and wetlands and spot the partially filled mine cut along the top of the ridge.  

At Quinebaug Woods in nearby Holland, trek a one-mile loop trail north along the Quinebaug River before turning west and heading up and over a “hogback”—an exposed, rocky ridge. Keep an eye out and you’ll find a stone chimney and some foundation steps; the remains of a cabin built in 1932. 

For Those Looking to Learn: History, Art, and Culture in the MetroWest

The Old Manse, Fruitlands Museum, and deCordova Sculpture Park and Museum

Are you a history, art, or culture buff? Look no further than a museum adventure West of Boston at Fruitlands Museum, deCordova Sculpture Park and Museum, and The Old Manse, which combine all three for the perfect one-day outing. 

Start your day by venturing out to Harvard to visit Fruitlands Museum. With some of the best scenic vistas in Massachusetts, Fruitlands is beautiful on an autumn morning. Take in the landscape by hiking miles of trails through 210 acres of conservation land, past Shaker buildings and the historic farmhouse. Visit the Museum’s art galleries to view the latest exhibitions. Visit the Fruitlands Museum Store for a memento before hitting the road to your next stop. 

If you’d like to experience Fruitlands with the help of an expert, join The Making of a Museum: A Fruitlands Story, new this fall.  

Your next stop is deCordova Sculpture Park and Museum in Lincoln. Enjoy the beauty of the sculpture park in autumn, as leaves fall around the intriguing art that dots the property. Join a sculpture park tour or take in the art at your own pace.

A visit to the deCordova Museum Store is a must, and you can grab a bite at the Twisted Tree Cafe, before setting off for Concord and The Old Manse. 

The Old Manse sits at the intersection of multiple histories—revolutionary and literary, among others. A fascinating place to visit in the year of America’s 250th Anniversary, The Old Manse is constantly offering tours that lift the veil on the many stories of the property. After you join a tour, explore the grounds and walk the network of easy footpaths linking the Old Manse to the North Bridge, site of the famous “shot heard round the world.” 

For Solo Trekkers: Serenity on the South Coast

Cornell Farm, Slocum’s River Reserve, and Westport Town Farm

Head out on a solo walk across historic farmlands, woodlands, and wetlands at Cornell Farm, Slocum’s River Reserve, and Westport Town Farm on the South Coast.

Cornell Farm in Dartmouth offers the perfect starting point. A family agricultural enterprise for five generations, this 130-acre property is among a cluster of historic salt farms that have earned treasured status along Buzzards Bay and the South Coast.  Wander past the fields and enter a beautiful oak-holly forest, which transforms with the season. Trails provide broad views of the marsh, and connect to adjacent open space, offering a chance to continue your walk.

A few miles away is the next stop, Slocum’s River Reserve, also in Dartmouth. Amble along two miles of woodland trails before reaching the western shoreline of the river, an expanse of tidal flats. More than 3,000 feet of critical shoreline and salt marsh have been protected here.  

For a longer excursion, follow a 3.6-mile trail that passes through a thick forest of pine and oak and loops around the adjacent Dartmoor Farm Wildlife Management Area, a property of the state Division of Fisheries and Wildlife. 

Continue the river views by heading to Westport Town Farm in Westport, which offers beautiful agricultural vistas. Explore this historic landscape along the easy, one-mile trail from the barnyard, which follows along stonewall-lined paddocks. As the trail crosses hillside pastures, it offers a scenic view of the East Branch of the Westport River, then skirts the ten-acre hayfield before returning to the barnyard.  

Whatever your cup of tea (or cider), this fall, The Trustees has a day trip perfect for you. Expand your horizons and head out to sites across the state—exploring somewhere new is sure to inspire, with lasting memories to cherish.

Before you set out, check property pages for details about hours of operation.