The 11 Best Fall Day Trips from Boston

If you live in Boston or are visiting the city in the fall, here are some suggested fall day trips you can take by bus, or set out in your car for scenic autumn destinations within a two-hour drive of Boston, Massachusetts.​ Need to rent a car? Compare car rental rates at Expedia.

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    Set out from Boston on a nine-hour motorcoach tour of the New England countryside this fall. The trip includes a stop at an orchard for apples and cider. Book your seat on the Fall Foliage Sightseeing tour via Viator.com.

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    Book via Viator.com and a motorcoach will take you out of Boston for an eight-hour pilgrimage to Plymouth, Massachusetts, the historic home of the Pilgrims. You'll be on your own to explore Plimoth Plantation, Plymouth's waterfront, Plymouth Rock, Mayflower II and other historic sites. Monday, Wednesday and Friday departures are available through late October.

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    Salem Halloween
    Media photo courtesy of the Massachusetts Office of Travel and Tourism.

    Salem, Massachusetts, is just 25 miles north of Boston, and the spooky city where the Salem Witch Trials took place in 1692 is easily accessible via car or MBTA trains, or book a spot on a Salem-bound bus tour direct via Viator. October is a particularly good time to visit Salem--in addition to the town's normal host of bewitching attractions, you'll find a full calendar of Haunted Happenings.

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    America's Stonehenge
    J. Miers - User: (WT-shared) Jtesla16 at wts wikivoyage/Wikimedia Commons/CC-BY-SA-3.0

    You've probably heard of Stonehenge--that mysterious collection of megaliths (big rocks) over in the old England. But did you know that New England has its own Stonehenge in Salem, New Hampshire, just a 40-minute drive from Boston? Fall is the perfect season for a day trip to this mysterious attraction.

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    Walden Pond
    ptwo from Allahabad, India/Flickr/CC-BY-2.0

    Walden Pond covers 62 acres, but it's really much larger than that. Few bodies of water have celebrity status to rival that of this serene pool in Concord, Massachusetts. 19th-century writer Henry David Thoreau is, of course, responsible for turning the pretty pond into an icon. See photos and learn how you can visit this scenic spot in the fall. It's just a 35-minute car trip from Boston in Concord, Massachusetts.

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    Davis' Mega Maze Near Boston
    Media photo courtesy of the Massachusetts Office of Travel and Tourism

    New England's oldest and largest cornfield maze is the 8-acre Mega Maze at Davis' Farmland in Sterling, Massachusetts. Leave Boston behind for a scenic hour and 10-minute drive to this challenging, larger than life puzzle, where you can "get lost" for a while this fall and have loads of fun in the process.

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    Center Meetinghouse, Old Sturbridge Village Massachusetts
    John Phelan/Wikimedia Commons/CC-BY-SA-3.0

    Old Sturbridge Village is a 200-acre time machine that transports visitors to the early 1800s. Within moments of setting foot inside the complex of historic buildings populated with authentically costumed "interpreters," you can't help but feel immersed in yesteryear. Old Sturbridge Village is the Northeast's largest living history museum, a place where the routines and rituals of a 19th-century New England community play out day after day, season after season. Autumn is harvest season at Old Sturbridge Village, a fascinating and picturesque time for a visit. It's an easy day trip destination from Boston, located just over an hour's drive from the city.

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    The estate and view from Castle in the Clouds, also known as Lucknow, in Moultonborough, New Hampshire.
    Fletcher/Wikimedia Commons/CC-BY-4.0

    Just over a two-hour drive from Boston in Moultonborough, New Hampshire, you'll be stunned by the fall views from Castle in the Clouds, the spectacular, 5,500-acre estate built by eccentric industrialist Thomas Plant in 1914. Pause and hike to a waterfall on your drive up to this mountaintop abode, and, after your castle tour, linger over lunch or snacks and drinks at the Castle Cafe in the Carriage House.

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    Hyland Orchard & Brewery, located just over an hour's drive from Boston in Sturbridge, Massachusetts, is a fun place for the whole family on weekends in the fall. Through October, Hyland offers apple picking and live music on weekends. Kids love wagon rides and the petting zoo. Adults can sample beer in the barn turned home of Rapscallion Brewery.

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    Newburyport: Walk Around this Waterfront Town North of the City

    This waterfront town is under an hour from Boston and the perfect day trip if you're looking to explore a new town when the weather is nice. Newburyport not only has a marina, but it is home to several popular restaurants and bars. Also nearby is Plum Island, a beautiful beach destination.

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    Portsmouth: Cross the Border to New Hampshire's Seacoast

    Portsmouth, NH

    Traveling to another state may not sound like a day trip, but there's plenty to see just over the New Hampshire border, which is about an hour away from Boston. Here you'll find Portsmouth, another cute waterfront town with plenty of shops, restaurants, hotels and more. Portsmouth is within close proximity to several beaches as well and it is beautiful no matter what time of year.