6 Coolest Towns in Massachusetts for a Summer Vacation
Tanglewood’s lawn fills with picnic blankets every summer Friday while the Boston Symphony plays under the Berkshire sky. Provincetown throws Carnival at the tip of Cape Cod every August. In Rockport, the red fishing shack known as Motif #1 has been painted by more artists than almost any building in America. Nantucket’s Opera House Cup fills the harbor with classic wooden sailboats. Concord still holds the Old North Bridge from the opening shots of the American Revolution. Six Massachusetts small towns where summer runs cooler than the rest of the country.
Rockport
Rockport makes for a strong beach getaway. The small town has many secluded beaches with a craggy, weather-beaten look. Visitors can head to Front or Back Beach, Old Garden Beach, and Long Beach to explore tidal pools, dip their toes in the water, ride the waves, or enjoy a long walk.
June or July is a great time to visit, especially for music lovers. Each year, the town hosts the Rockport Chamber Music Festival, with performances from blues, jazz, and indie singers across a roughly month-long run.
Lenox
Another place for music lovers, Lenox hosts its annual Tanglewood Music Festival throughout June and July. Each year’s lineup typically features a mix of classical performances by the Boston Symphony Orchestra and popular touring artists.
For a quiet outdoor experience, visitors can explore the 500 acres of Kennedy Park. The park offers 15 miles of hiking trails, an observation point, and old carriage roads through hardwood forests.
Pleasant Valley Wildlife Sanctuary is an equally good option. It has 7 miles of hiking trails and 1,300 acres of wetlands, forests, and meadows. Visitors can also go canoeing or birdwatching through the sanctuary.
Concord
Immerse yourself in the rich history of Concord. The town, along with Lexington, was the site of the opening battles of the American Revolution in 1775. For history buffs, the Old North Bridge (a crucial part of the battle) and the Concord Museum are must-see attractions.
Concord also has a deep literary history. The town was once home to Louisa May Alcott, the author of Little Women. The home that inspired her novel, Orchard House, still stands today and is open to the public. Visitors in June can purchase tickets to the annual Garden Tour to view six private gardens around town.
Provincetown
Located on the northernmost tip of Cape Cod, Provincetown is a welcoming small town with wide beaches. Each August, thousands of people flock to Ptown for Carnival, a summer celebration of creativity and community. The festival hosts costume contests, a parade, parties, and performances.
Once Carnival is over, head to Herring Cove Beach to catch the sunset and enjoy live music on Wednesdays and Sundays. Visitors can rent a bike and explore the Province Lands Bike Trail, which meanders past pine forests, dunes, and cranberry bogs.
Shelburne Falls
Situated on the banks of the Deerfield River is Shelburne Falls, which was once a popular fishing ground for Native Americans. Its Victorian-era core forms a historic district listed on the National Register of Historic Places.
Things to do in town include a stop at the Bridge of Flowers. Located in the heart of Shelburne Falls, what was once a trolley bridge is now a flower garden maintained by volunteers. The bridge is open during the summer through October.
For more outdoor exploring, visitors should check out High Ledges Wildlife Sanctuary. The hike offers views of the Deerfield River and Mount Greylock. During spring and summer, the wildflowers in the river valley are in full bloom.
Nantucket
Nantucket, with summer temperatures in the 60s to 70s, fills with visitors during summer for the town’s many events and the flower-filled gardens that come alive in season.
The annual Fourth of July event is a must-visit, not just for the fireworks but for the farmer’s market, food trucks, and the water competition on Main Street between the reserve fighters and the fire department.
In August, the town hosts the annual Opera House Cup, a sailing race that fills the harbor with colorful boats. Also in August, the Boston Pops typically visits Nantucket for an annual benefit performance for Nantucket Cottage Hospital at Jetties Beach.
Summer in Massachusetts’ Small Towns
From the Rockport Chamber Music Festival and Ptown’s Carnival to the Opera House Cup in Nantucket and the Bridge of Flowers in Shelburne Falls, these Massachusetts towns offer visitors a long list of events to enjoy this summer.
Each of these towns has its own character, surrounded by natural beauty, and welcomes visitors. If you’re planning your next summer vacation and prefer the peace of small-town living, consider visiting these six towns in Massachusetts.
