5 Perfect New England Foliage Day Trips from Boston

One of the best things about living in Boston is the relative ease of leaving the city behind and immersing yourself in rural pleasures. As the days get shorter and the trees turn Technicolor, don’t miss the chance to hit the road and visit the best destinations for easy New England foliage day trips. After all, within two and a half hours of the city are some incredible, very accessible destinations. Here are our favorites.

Stow, MA

Miles from Boston: About 30
Approximate driving time: 45 minutes

Due west and a bit north of the city, the town of Stow boasts a landscape of curving country roads lined with maples and stone walls. While this is not a place for wide views and big mountains, it is quintessentially New England. It’s home to Honey Pot Hill Orchards, the most popular pick-your-own destination within the I-495 loop. Generations of families come here to harvest their own fruit, wander the Big Green Monster Maze, and pick up pumpkins and cider doughnuts from the farm. (On your way in, take note of Mistletoe Christmas Tree Farm around the corner and make plans to come back in December.) Two other PYO farms, Shelburne Farm and Carver Hill Orchard, offer a mellower setting, while the farm stands at Applefield Farm and Small Farm will satisfy all your Green Acres fantasies. Take a walk at the Assabet River National Wildlife Refuge, where a network of hiking and biking trails take you close up to the unique beauty of wetlands in the fall. And just one town over, in Hudson, you’ll find one of the most fascinating below-the-radar museum experiences at the American Heritage Museum, which explores this country’s military history from the Revolution onward. Finish your day with delicious scoops at New City Microcreamery.

Peterborough, NH

Miles from Boston: About 80
Approximate driving time: 1 hour, 30 minutes

This small town in southern New Hampshire punches far above its weight as a fall foliage destination. Bordered by mountains and located along the Contoocook River, Peterborough was the model for Thornton Wilder’s Pulitzer Prize–winning play, Our Town, but it shines today as an antiques lover’s magnet that also attracts outdoor enthusiasts and artists. While Mount Monadnock, which draws 125,000 hikers each year, is just down the road, locals flock to Miller State Park, which has several trails (and an auto road) leading to the 2,290-foot summit of Pack Monadnock. If antiquing is more your speed, check out Twin Elm Farm, ReMarkable, Grove & Main Antiques, and Bowerbird & Friends. Shoppers should also be sure to visit the locally beloved Toadstool Bookshop. Hungry? Try Waterhouse for fine dining by the Contoocook River, Harlow’s Pub for great beer and comfort food, and Pearl for Asian-inspired seafood.

Shelburne Falls, MA

Miles from Boston: About 110
Approximate driving time: 2 hours

Shelburne Falls, a standout on our list of the Prettiest Fall Foliage Villages in Massachusetts, is surrounded by hills, so blockbuster fall color is a given here. But anchoring the surrounding beauty is the Bridge of Flowers, a former trolley bridge lined with stunning perennial gardens that stretches over the Deerfield River to connect the villages of Shelburne and Buckland. Take a look at the glacial potholes, also downtown, where water has worn away a granite ledge over thousands of years to create little pools up to 39 feet in diameter. The other great natural wonder is just up the road in Shelburne, where Apex Orchards has gorgeous fruit and a vast view of Western Massachusetts, Vermont, and New Hampshire. Back in town, the Shelburne Falls Bowling Alley is one of the oldest bowling alleys in the country, as well as one of the few places in New England where you can still enjoy candlepin bowling. For breakfast, pop into the bakery/restaurant Baked for apple fritters and terrific egg sandwiches on homemade biscuits, then browse local fine arts and crafts at the Shelburne Arts Co-Op and Salmon Falls Gallery. Boswell’s Books is a bibliophile’s dream, and Mocha Maya’s will keep you happily caffeinated. As the day winds down, settle in for dinner at Gypsy Apple Bistro for seasonal French classics or The Blue Rock for great farm-to-table fare.

Woodstock, VT

Miles from Boston: About 145
Approximate driving time: 2 hours, 20 minutes

The concentration of top-notch sporting, shopping, and dining options is remarkable for this central-Vermont town of just 3,000 year-round residents. One of the most photographed covered bridges in New England, the Middle Bridge, is right in the heart of town, near the grande dame Woodstock Inn & Resort.And hiking up Mount Tom takes a mere 30 minutes from town (the trail begins on Mountain Avenue, behind the covered bridge), and the summit provides a stunning view of the entire village. Beyond that one hike, you’ll find a network of interconnected trails throughout and around the town. Browse artisan wares at the home-goods shop Farmhouse Pottery, grab a book from the well-curated selection at the Yankee Bookshop, and don’t miss the Woodstock Farmers’ Market, stocked with Vermont-made cheeses, chocolates, and other edible marvels. You could spend a whole afternoon at F.H. Gillingham & Sons, a sprawling general store that first opened its doors in 1886. It is still family-owned and filled with everything from gardening essentials to fishing tackle to toys and gluten-free crackers. Billings Farm and Museum offers a taste of traditional New England farm life c. 1890, with such things as butter-making and sheep-shearing demonstrations, while the mansion at the Marsh-Billings-Rockefeller National Historical Park provides a stunning example of Queen Anne–style architecture.

You can caffeinate with the locals at Mon Vert Café, which specializes in terrific pastries, sandwiches, and coffee drinks. Worthy Kitchen offers craft beer and primo comfort fare (burgers, poutine, fried chicken, local cheeses). Mountain Creamery is a great place to grab a VerMonte Cristo sandwich (ham, turkey, and Swiss between French toast slices, served with a side of maple syrup) and a slice of mile-high apple pie. Finally, for upscale dining, try the Lincoln Inn & Restaurant, where chef Jevgenija Saromova takes years of restaurant training in Italy, England, and France and applies them to the seasonal flavors of Vermont. Or, head to South Woodstock, where the Ransom Tavern in the Kedron Valley Inn serves excellent Neapolitan-style pies and antipasti in a modern tavern setting.

Stockbridge, MA

Miles from Boston: About 130
Approximate driving time: 2 hours, 30 minutes

Tucked into the Berkshire Hills, Stockbridge is the little town that inspired Norman Rockwell’s most idyllic depictions of American life, and its charms come into sharp focus in the fall. While still maintaining its village feel, Stockbridge draws throngs of visitors each year who come to stay and eat at one of the nation’s oldest continuously operating historic inns, the Red Lion Inn, and tour a museum dedicated to Rockwell’s work. The Tanglewood season may be over, but culture vultures should also check out the powerhouse Berkshire Theater Group’s Unicorn Theater, which hosts live music and work from emerging playwrights in a rambling barn-red playhouse, as well as the TurnPark sculpture park and performance space. And if you want to get into nature, try Laura’s Tower Trail, which leads up to a metal tower offering wide views of the Berkshires, Catskills, and Green Mountains. Shoppers will love to wander the treasure-filled Williams & Sons Country Store, and bibliophiles should head to West Stockbridge and visit Shaker Mill Books for new, used, and rare volumes. While there, grab a coffee and a bite at Six Depot Roastery and Café, and pick up some vanilla extract from Charles Baldwin & Sons, established in 1888.