7 Best Fall Day Trips from Boston, Massachusetts
Fall in New England is something everyone should experience at least once.
The crisp air, vibrant foliage, and charming small towns create the perfect backdrop for a memorable day trip.
You’re here because you want to escape the hustle and bustle of Boston for a day and soak in the seasonal beauty of the surrounding areas.
Whether you’re a local or just visiting, these day trips offer a refreshing break and a chance to explore some of the best that Massachusetts and the nearby states have to offer.
Boston is a fantastic city, but sometimes you need a change of scenery, especially in the fall.
I wrote this article to help you discover some of the best places to visit within a short drive from the city.
Inside, you’ll find a mix of classic New England towns, scenic coastal spots, and hidden gems that are all within reach for a perfect autumn day trip.
Whether you’re looking to hike, shop, or simply enjoy the fall colors, there’s something here for everyone.
1. Salem, Massachusetts
Salem, known for its infamous witch trials, is a must-visit during the fall, especially around Halloween.
The town comes alive with spooky decorations, haunted tours, and festive events that celebrate its eerie history.
Beyond the witch-themed attractions, Salem offers beautiful waterfront views, historic homes, and a charming downtown filled with unique shops and cafes.
A visit to the Salem Witch Museum or a stroll through the historic Chestnut Street will give you a deeper appreciation for this town’s rich past.
2. Concord, Massachusetts
Concord is a quintessential New England town that’s rich in history and literary significance.
In the fall, the town’s tree-lined streets and historic sites are surrounded by stunning foliage.
Visit Walden Pond, where Henry David Thoreau penned his famous work, or take a walk through the historic Battle Road Trail, where the first battles of the American Revolution took place.
Concord’s downtown area is also worth exploring, with its charming shops, cafes, and the Concord Museum, which offers insight into the town’s storied past.
3. The Berkshires
A day trip to the Berkshires is perfect for those looking to immerse themselves in the beauty of nature.
This mountainous region in western Massachusetts is renowned for its vibrant fall foliage, making it a popular destination for leaf-peeping.
Take a scenic drive along Route 7, hike to the top of Mount Greylock (the highest point in the state), or visit the quaint towns of Lenox and Stockbridge, which offer a mix of cultural attractions, art galleries, and cozy cafes.
The Berkshires also host a variety of fall festivals and events, adding to the area’s charm.
4. Ipswich, Massachusetts
Located just north of Boston, Ipswich is a coastal town known for its stunning beaches and historic homes.
In the fall, the town’s natural beauty is enhanced by the changing leaves, making it an ideal spot for a day trip.
Visit Crane Beach, one of the most beautiful beaches in New England, or explore the Crane Estate, a grand historic mansion set on 2,100 acres of landscaped grounds.
Ipswich is also famous for its clams, so be sure to stop by one of the local seafood shacks for a taste of this local delicacy.
5. Stowe, Vermont
While a bit of a longer drive, Stowe, Vermont, is well worth the trip for its breathtaking fall scenery.
This picturesque town is nestled in the Green Mountains and offers some of the best leaf-peeping in New England.
Take a drive along the scenic Route 100, hike the trails on Mount Mansfield, or simply stroll through the charming downtown area, which is filled with boutique shops and cozy cafes.
Stowe’s vibrant foliage, combined with its small-town charm, makes it a perfect destination for a fall day trip from Boston.
6. Rockport, Massachusetts
Rockport, a small seaside town on Cape Ann, offers a perfect blend of coastal beauty and artistic charm.
In the fall, the town’s harbor and rocky coastline are framed by the vibrant colors of autumn, creating a stunning backdrop for a day of exploration.
Visit the iconic Motif No. 1, a red fishing shack that’s one of the most painted buildings in America, or explore the many art galleries and shops along Bearskin Neck.
Rockport is also home to some great seafood restaurants, making it a perfect spot for a leisurely lunch or dinner by the sea.
7. Lexington and Concord, Massachusetts
For history buffs, a day trip to Lexington and Concord is a must.
These neighboring towns played a pivotal role in the American Revolution, and their historic sites are especially beautiful in the fall.
Walk along the Battle Road Trail, visit the Minute Man National Historical Park, or explore the homes of famous authors like Louisa May Alcott and Nathaniel Hawthorne.
The fall foliage adds an extra layer of beauty to these historic landscapes, making it a great time to visit and reflect on the country’s early history.
Conclusion, 7 Best Fall Day Trips from Boston, Massachusetts
Boston is surrounded by a wealth of beautiful and historic destinations, each offering something unique during the fall season.
From the spooky streets of Salem to the scenic mountains of the Berkshires, these day trips provide the perfect opportunity to experience the best of New England’s autumn charm.
Whether you’re looking for history, nature, or just a peaceful escape, these spots are sure to make your fall unforgettable.
So grab your camera, pack a cozy sweater, and hit the road to explore the best of Massachusetts and beyond this fall.
