The 11 Best Fall Day Trips From Boston

America's Stonehenge: Visit Historic Dwellings

You've probably heard of Stonehenge—that mysterious collection of megaliths (big rocks) over in the old England. You may not know that New England has America's Stonehenge in Salem, New Hampshire, just a 40-minute drive north from Boston. Fall is the perfect season for a day trip to this curious attraction, which features 30 acres of dwellings that resemble caves and stone structures built according to an astronomical calendar, a visitor center, and more.

Davis Farmland Discovery Farm: Explore the Mega Maze

One of New England's oldest and largest cornfield mazes is the 8-acre Mega Maze, typically held through early November at Davis Farmland Discovery Farm in Sterling, Massachusetts. Leave Boston behind for a scenic roughly one hour, 10-minute drive to this challenging, larger than life puzzle. You can have loads of fall fun, as well as catch some live music and choose from many food options.

Across the street at Davis Farmland, enjoy picking apples and pumpkins, spray grounds, an animal showcase, and more. Buy tickets online in advance for both attractions.

Old Sturbridge Village: Get Transported to the 1800s

Old Sturbridge Village in Sturbridge, Massachusetts, is a 200-acre time machine that transports visitors a New England town in the early 1800s. Within moments of setting foot inside the complex of historic buildings populated with interpreters in 19th-century attire, you can't help but feel immersed in yesteryear. The Northeast's largest outdoor history museum, Old Sturbridge Village displays the routines and rituals of a past community day after day, season after season.

Fall is a fascinating and picturesque time for a visit. A special Autumn Harvest Weekend usually includes a chance to see farm animals and artisans as well as learn from the costumed interpreters as they pick corn, potatoes, and more. The village is an easy day trip destination from Boston, located just over an hour's drive from the city.

Castle in the Clouds: Catch Stunning Views

As of late October 2020, the Carriage House Restaurant is temporarily closed, but Café in the Clouds serves lunch every day from 11 a.m. to 4 p.m. Just over a two-hour drive from Boston in Moultonborough, New Hampshire, Castle in the Clouds features stunning fall landscapes at a mountaintop abode. The spectacular, 5,500-acre estate was built by eccentric industrialist Tom Plant in 1914 and boasts a lovely view of Lake Winnipesaukee. Hike among the 28 miles (45 kilometers) of trails, or stroll by some waterfalls. After a one-hour walking tour, linger over lunch or snacks and drinks at the Carriage House Restaurant, which caters to vegetarian and gluten-free diets.

Newburyport: Stroll Around the Waterfront Town

Newburyport, Massachusetts, a waterfront town only an approximately 45-minute drive north of Boston, makes the perfect day trip. The autumn season is a great time to explore the town and enjoy pleasant weather. Not only does the town have a marina and some nice parks, but it is home to several popular restaurants and bars. Some travelers enjoy shops with antiques, clothes, and more. In addition, the beautiful beach destination of Plum Island is nearby. Check out the Plum Island Lighthouse, also known as the Newburyport Harbor Lighthouse, where open houses take place on the third Sunday from May through September.

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Portsmouth: Shop and Eat at the Seacoast

Traveling to another state may not sound like a day trip, but there's plenty to see just over the New Hampshire border in Portsmouth, which is only about an hour away from Boston by car. Portsmouth is a cute, historic waterfront city dating back to 1630 with plenty of shops, art galleries, restaurants, breweries, hotels, and more. It is within close proximity to several beaches as well and is beautiful no matter what time of year you visit.

New England Countryside: Take a Fall Foliage Bus Tour

The Fall Foliage Bus Trip is canceled in 2020. Set out from Boston on an approximately nine-hour motorcoach tour of the New England countryside. This one-day trip held each autumn includes a stop at an orchard for apples and cider and views of lovely towns, taverns, churches, Willard Brook State Forest, and more. Book through Viator for the Fall Foliage Sightseeing tour, which includes lunch.

Plimouth Plantation: Learn About the Pilgrims

The Plymouth Day Trip is canceled in 2020. Reserve via Viator and board a motorcoach from Boston for an eight-hour pilgrimage to Plymouth, Massachusetts, the historic home of the Pilgrims. You will enjoy a guided tour of the Plimoth Plantation living history museum, the working Plimoth Grist Mill, the local waterfront, Plymouth Rock, Mayflower II, and other historic sites. The seasonal tour usually runs from June to October.

Salem: Get Spooked During Halloween

The Boston to Salem "Witch City" Day Trip is canceled in 2020. Salem, Massachusetts, is just 25 miles (40 kilometers) north of Boston, and the eerie city where the Salem Witch Trials took place in 1692 is easily accessible via car or MBTA trains. You can also book a spot on a roughly seven-hour Salem-bound bus tour direct via Viator. October is a particularly good time to visit Salem—in addition to seeing the town's Halloween shops and witch-related attractions, you'll have lunch in the Pickering Wharf area.

Walden Pond: Walk or Swim on the Famous Beach

Walden Pond Visitor Center, the Thoreau House Replica, and the picnic areas are temporarily closed as of late October 2020. The Walden Pond State Reservation spans about 400 acres including the pond and surrounding areas. Few bodies of water have celebrity status to rival that of this serene pool in Concord, Massachusetts. Henry David Thoreau, the 19th-century writer, turned the pretty pond into an icon when he lived there for two years. The fall is a lovely time to walk, swim, and ride a boat at this scenic spot, which is just a 35-minute car trip west from Boston.

Hyland Orchard: Enjoy Fun for the Whole Family

The Hyland Orchard is closed for the 2020 season. Located about an hour's drive from Boston in Sturbridge, Massachusetts, this is a fun place for the whole family on autumn weekends. Hyland Orchard typically offers apple picking and live music on Saturdays and Sundays through October. Kids love wagon rides and the petting zoo. Adults can sample beer in the Rapscallion Brewery & Tap Room, housed in a 1940s apple barn, while enjoying something to eat from the food truck on-site.