6 Coolest Towns in Massachusetts for a Summer Vacation in 2024
No summer vacation is complete without a day at the beach. Luckily, Massachusetts is the perfect destination for a coastal holiday. The big cities of Salem and Boston often get more notice in Massachusetts, however, several small towns within the state promise vacationers a unique and memorable experience.
Let’s explore six of the coolest towns in Massachusetts with historical, natural, and commercial attractions, and quaint atmospheres for an unforgettable 2024 summer vacation.
Rockport
Fishing boat harbor in Rockport, Massachusetts, United States, a town located in Essex County.
Rockport makes for an ideal beach getaway. The small town has many fantastic, 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 2024 is a great time to visit, especially for music lovers. Each year, the town hosts the Rockport Chamber Music Festival. It will be held from June 7 to July 7, 2024, and feature performances by blues, jazz, and indie singers.
Lenox
The Mount, Lenox, Massachusetts, USA. Editorial credit: Heidi Besen / Shutterstock.com
Another great spot for music lovers, Lenox will host its annual Tanglewood Music Festival throughout June and July 2024. This year's lineup will feature performances by Jon Batiste, Brandi Carlile, Jason Mraz, and the Boston Pops.
For a quiet, rejuvenating 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 amidst serene hardwood forests.
Pleasant Valley Wildlife Sanctuary is an equally pleasant experience. It has 7 miles of hiking trails, and 1300 acres of wetlands, forests, and meadows. Additionally, visitors can go canoeing or bird watching through the Sanctuary.
Concord
The historic town center of Concord, Massachusetts, USA. Editorial credit: Wangkun Jia / Shutterstock.com
Immerse yourself in the rich history of Concord. The town, along with Lexington, was the site of the first battle 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 spectacular literary history. The town was once home to the author of Little Women, Louisa May Alcott. The home that inspired her novel, Orchard House, still stands today and is open to the public. People visiting in June 2024 may like to purchase tickets to the 25th Annual Garden Tour to view six uniquely beautiful private gardens around town.
Provincetown
Tranquil scene at Commercial Street in Provincetown, Massachusetts. Editorial credit: Rolf_52 / Shutterstock.com
Located on the northernmost tip of Cape Cod lies Provincetown. It is a welcoming small town with gorgeous beaches. In August 2024 (17th to 24th), thousands of people will 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. For an invigorating activity, visitors can rent a bike and explore the Province Lands Bike Trail which meanders past pine forests, dunes, and cranberry bogs.
Shelburne Falls
The Bridge of Flowers spans the Deerfield River in Shelburne, Massachusetts during fall.
Situated on the banks of the Deerfalls River is Shelburne Falls, which was once a popular fishing ground for Native Americans. Known for its Victorian architecture, the entire town is now on the National Register of Historic Places.
Things to do in town include a stop at the Bridge of Flowers. It is located in the heart of Shelburne Falls and what was once a trolley bridge is now a beautiful flower garden maintained by volunteers. The bridge is open during the summer from August to October.
For more natural adventures, visitors should explore High Ledges Wildlife Sanctuary. The hike offers breathtaking views of the Deerfalls River and Mount Greylock. During spring/summer, the wildflowers in the river valley are in full bloom.
Nantucket
The entrance of Nantucket, Massachusetts.
Nantucket, with temperatures in the 60s to 70s, is teeming with visitors during summer because of the town’s many events and because it comes alive in summer with lush, flower-filled gardens.
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 will visit Nantucket to perform for the Nantucket Cottage Hospital at Jetties Beach.
Discover Summer Magic 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 plethora of fun-filled activities to enjoy this summer.
Each of these towns is charming, surrounded by natural beauty, and welcomes visitors with open arms. So, if you’re planning your next summer vacation, and prefer the peace of small-town living, consider visiting these six coolest towns in Massachusetts.
