10 Best Things to Do in Massachusetts This Summer 2025
Discover the 10 best things to do in Massachusetts this summer, from seaside feasts and art in nature to battle reenactments, jazz under the stars, and oyster-fueled workdays.
By Kim Knox Beckius|Apr 24 2025|
Oversized garments mix ancient traditions and modern influences in Jeffrey Gibson’s Power Full Because We’re Different at Mass MoCA.
Photo Credit: Tony LuongLooking for the best things to do in Massachusetts this summer? From slurping oysters on the bay to celebrating Revolutionary history with an epic reenactment, these 10 unforgettable experiences showcase the creativity, culinary innovation, natural beauty, and cultural depth that make Massachusetts a must-visit summer destination. Whether you’re up for van life, jazz on the Cape, or contemporary art in the Berkshires, there’s something here to inspire every kind of traveler.
10 Best Things to Do in Massachusetts This Summer
1. Get Out of Your Shell in Duxbury – Wi-Fi, oysters, and lobster dip—your new favorite workday trio.
If your job allows you to work from anywhere, why wouldn’t you choose an outdoor table at The Raw Bar at Island Creek Oyster Farm in Duxbury? The Wi-Fi is reliable. Serene bay views and hyperlocal oyster selections will help clear your head. And there’s no task that can’t be made more palatable with a side of cheesy baked lobster dip.
Photo Credit : Island Creek Oysters
2. Supper by the Sea at Wequassett – Celebrate 100 years of Cape Cod elegance with family-style seaside feasts.
Turning 100 is a big deal, so Supper on the Bay gatherings will have extra sparkle this year at Harwich’s Wequassett Resort and Golf Club. On Thursday evenings in August, you can claim a seat at a long seaside table and dine in family-style lavishness on the freshest sea fare and produce that Cape Cod has to offer.
3. Raise a Baton to Keith Lockhart – Tanglewood toasts a Boston Pops legend with star-studded flair.
They called him “The Kid” when Keith Lockhart took the baton of the Boston Pops at the age of 35. More than 2,200 concerts later, his dynamic tenure as the face and grace of America’s Orchestra will be toasted August 22 at Tanglewood in Lenox with a 30th anniversary celebration featuring Bernadette Peters, Ben Folds, Lynn Ahrens, and other special guests.
4. Curl Up at An Unlikely Story – Books, beer, and community at Jeff Kinney’s charming indie bookstore.
If you recognize the name Jeff Kinney, you probably know a tween who’s devoured his Diary of a Wimpy Kid book series. But did you know Kinney and his wife, Julie, have owned a destination bookstore in Plainville for 10 years? While Kinney admits An Unlikely Story isn’t exactly making him rich, he’s undeterred in his drive to revitalize everything that surrounds his downtown shop, once a general store. Pitch in by attending one of the many author talks held in the Second Story event space, or by curling up in the café with a matcha latte and a mystery or a beer and a biography.
5. Power Up at Mass MoCA – Jeffrey Gibson’s show electrifies with queer, Indigenous energy.
Enormous garments suspended from tipi poles. Glass dance floors pulsing with kaleidoscopic light. Films. Soundtracks. Insights. The Jeffrey Gibson exhibit Power Full Because We’re Different has swept into massive Building 5 at North Adams’s Mass MoCA with an energy that electrifies the daunting space. Gibson, who last year became the first solo Indigenous artist to represent the U.S. at the Venice Biennale, is known for multifaceted installations like this, celebrating queer and Indigenous communities and giving voice and visibility to two-spirit gender expression.
Photo Credit : Sara Bill Photography for Walden Campervans
6. Hit the Road with Walden Campervans – Embrace van life and explore New England off-grid in style.
“Van life” appeals to all ages, and Acton-based Walden Campervans offers fully outfitted vehicles—some even dog-friendly—that make it easy to try this way of vacationing. Owners Mike and Susie Patrick go the extra mile, creating complimentary customized itineraries that showcase New England’s most exceptional off-the-grid destinations. Mike joined Weekends with Yankee cohost Richard Wiese for a campervan adventure in Maine this season that might just inspire your own road trip (check your local PBS listings).
7. Dine Fresh at Cantina 229 – Farm-to-table magic and hyperseasonal menus in the Berkshires.
Like an unexpected mirage on a Berkshires back road, Cantina is a glowy little restaurant that enchants from the get-go. Reopened last fall in New Marlborough by new owners Peter Chapin and Maddie Austin, it takes farm-to-table to the next level: Most menu ingredients are grown or raised on Mill River Farm, which is run by Chapin and his mother, Jan Johnson. Sip a cocktail infused with fresh-picked herbs while you peruse the week’s hyperseasonal selections, and you’ll immediately feel part of a foodie community.
8. Make It an Artful Escape to New Salem – Realist masterpieces in a historic home turned museum.
Not even two years ago, ardent collectors Vincent and Laura Barletta transformed their beloved-for-generations family home into America’s first museum devoted exclusively to contemporary realist art. It hasn’t taken long for their New Salem Museum & Academy of Fine Art to attract lovers of the genre to the tiny town of New Salem. You’ll be mesmerized each time you visit and discover the walls of this 19th-century home sporting works by living masters and the icons—like John Singer Sargent and Andrew Wyeth—on whose shoulders they stand. Stop by New Salem General Store to pick up made-to-order sandwiches to enjoy on the patio.
9. Experience the Battle of Bunker Hill Reenactment – Revolutionary history comes alive in Gloucester’s immersive celebration.
The 250th-anniversary Reenactment of the Battle of Bunker Hill won’t be held in Boston, although the Bunker Hill Monument Association plans a June 17 commemoration at the obelisk that marks the battle’s actual location on Breed’s Hill. To accommodate spectators and several hundred reenactors, Gloucester’s Stage Fort Park will step in to play the battleground during two days of immersive events, June 21 and 22. You won’t just see the fighting unfold—you’ll learn how civilians of all classes, allegiances, genders, and races perceived, participated in, and were affected by the Revolutionary era.
10. Wander Through Outdoor Art – Sculptures, gardens, and meditative trails in the Berkshires.
It’s like meditation in motion, strolling among sculptural works beautifully sited in the great outdoors. In the Berkshires, you could spend a whole weekend encountering art in the wild. TurnPark Art Space in West Stockbridge has 16 acres of former quarry lands to explore year-round. In Lenox, The Mount installs a new array of contemporary juried works across 50 acres, open free to the public May 24–October 19. And sculptor Andrew DeVries gives visitors free range to frolic with the dancers and jesters along the Sculpture Trail at his gallery in Middlefield, 11 a.m. to 4 p.m. Friday through Sunday, May 16–October 19 (donations accepted).
See More: 2025 Massachusetts Travel Guide | Hotels, Dining & Attractions
What tops your list of the best things to do in Massachusetts this summer? Let us know!
