Great Road Trips a Short Drive out of Boston

Explore Boston's New England neighbors, from Cape Cod to Williamstown and beyond.

Get out of town! There’s plenty to do in the city in summer and early fall—from free concerts at the Hatch Shell to Boston Calling Block Parties to name a few, then there are world-class museums and plenty of history to take in. However, if you want to see what Boston’s neighbors have to offer, variety is only a tankful of gas away.


With a list of summer residents that includes past presidents and other celebrities, Cape Cod and the island of Martha’s Vineyard offer upscale delights and plenty of scenic beach views. However, not everyone comes for the sea and sand.

The Cape is also starting to turn heads for its growing wine scene. Cape Cod Winery offers nine varieties of wine, including Sauvignon Blanc and rosé. The vineyard sits on the site of a former strawberry farm and is just 3 miles from the ocean. First Crush Winery sources its grapes from the Suisun Valley AVA in Northern California, and offers wines ranging from Sangiovese to Sauvignon Blanc. Truro Vineyards produces over a dozen varietals each year and even hosts the occasional grape stomp.

Even further still lies Provincetown with its wealth of natural beauty, including parks and long stretches of white sand beaches. Most famous for being the site of the Mayflower’s landing in 1620, this little town (nicknamed P-Town) is also well-known for its advocacy of the LGBTQ community. Over 90,000 people make the trek each year for the August Provincetown Carnival to celebrate all things LGBTQ, with parties, art fairs, and performances. 


In the northeast tip of Massachusetts in Cape Ann, you’ll find the picturesque summer hideaways of Rockport and Gloucester. At Rockport, many come to stroll Bearskin Neck, an art-centric colony filled with rustic local shops and Motif #1, a little red shack dubbed “the most-often painted building in the world.” You can watch saltwater taffy being made at Tuck’s Candies, and try flavors ranging from peanut butter to cranberry and café latte.

The Rockport Music Festival is a huge draw and regularly attracts international stars and their fans. 


While Boston dominates the east end of the Bay State, don’t overlook all there is to do out west. On the way to the scenic Berkshires, be sure to drive through Amherst and stop by the Emily Dickinson Museum, the Yiddish Book Center and the Eric Carle Museum of Picture Book Art. Just outside of Amherst, you’ll also find the Mt. Holyoke Range State Park, which features 7 miles of mountain ridgeline and more than 30 miles of hiking trails.

Farther west still, a regular stop for many is the music venue Tanglewood in Lenox. Tanglewood is the Boston Symphony Orchestra’s summer home. Big draws include performances from stellar musicians such as Yo-Yo Ma.

Just 10 minutes from Lenox is Stockbridge’s Norman Rockwell Museum, celebrating its 50th anniversary with special exhibitions and events.

In the very northwest corner of Massachusetts,  in North Adams, MassMOCA (the Massachusetts Museum of Contemporary Art) is exhibiting music legend Annie Lenox. Catch the new exhibit “ERRE: Them and Us/Ellos y Nosotros.” 

While Logan International may be your point of departure, there are many other points around Boston and throughout New England that make for a fun get-away. All you have to do is give it a go.