The 6 Coolest Cities 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 vacation. The large cities of Salem and Boston are often more popular in Massachusetts, but several small towns in the state promise vacationers a unique and unforgettable experience.

Let's explore six of the coolest towns in Massachusetts with historic, natural and commercial attractions and a picturesque atmosphere for an unforgettable 2024 summer vacation.


Fishing boat harbor in Rockport, Massachusetts, USA, a town in Essex County.

Rockport is an ideal beach vacation. The small town has many fantastic, secluded beaches with a rugged, weather-beaten appearance. Visitors can head to Front or Back Beach, Old Garden Beach and Long Beach to explore tide pools, dip their toes in the water, ride the waves or enjoy a long walk.

June or July 2024 is a great time to travel, especially for music lovers. Every year the city hosts the Rockport Chamber Music Festival. It will take place from June 7 to July 7, 2024 and will feature performances by blues, jazz and indie singers.


The Mount, the former country home of the writer Edith Wharton in Lenox, Massachusetts, USA.

The Mount, Lenox, Massachusetts, USA. Photo credit: Heidi Besen /

Another great spot for music lovers, Lenox will host its annual Tanglewood Music Festival in June and July 2024. This year's program includes performances by Jon Batiste, Brandi Carlile, Jason Mraz and the Boston Pops.

For a quiet, relaxing outdoor experience, visitors can explore the 500-acre Kennedy Park. The park offers 15 miles of hiking trails, an overlook and old carriage roads amid quiet hardwood forests.

The Pleasant Valley Wildlife Sanctuary is an equally enjoyable experience. It has 7 miles of hiking trails and 1,300 acres of wetlands, forests and meadows. Additionally, visitors can canoe or bird watch through the sanctuary.


Main Streets Market and Café at 42 Main Street in historic downtown Concord, Massachusetts, USA.

Historic downtown Concord, Massachusetts, USA. Photo credit: Wangkun Jia /

Immerse yourself in Concord's rich history. The city, 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-sees.

Concord also has a spectacular literary history. The town was once home to Little Women author Louisa May Alcott. The house that inspired her novel, the Orchard House, still stands today and is open to the public. Visitors in June 2024 may wish to purchase tickets for the 25th Annual Garden Tour to tour six uniquely beautiful private gardens in the city.


Quiet scene on Commercial Street in Provincetown, Massachusetts.  Provincetown, the site of the Mayflower's first landing, is now a major tourist destination.

Quiet scene on Commercial Street in Provincetown, Massachusetts. Photo credit: Rolf_52 /

Provincetown is located at the northernmost tip of Cape Cod. It is a welcoming small town with beautiful 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 features costume contests, a parade, parties and performances.

When Carnival is over, head to Herring Cove Beach to enjoy the sunset and live music on Wednesdays and Sundays. For an invigorating activity, visitors can rent a bike and explore the Province Lands Bike Trail, which winds past pine forests, dunes, and cranberry bogs.

Shelburne Falls

The Bridge of Flowers spans the Deerfield River with the rolling hills of western Massachusetts as a backdrop in autumn in Shelburne, Massachusetts.

The Bridge of Flowers spans the Deerfield River in Shelburne, Massachusetts in the fall.

On the banks of the Deerfalls River lies Shelburne Falls, once a popular fishing destination for Native Americans. The entire city is known for its Victorian architecture and is now on the National Register of Historic Places.

Things to do in town include a stop at the Flower Bridge. 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 in summer from August to October.

For even more nature experiences, visitors should explore the High Ledges Wildlife Sanctuary. The hike offers breathtaking views of the Deerfalls River and Mount Greylock. In spring/summer the wildflowers in the river valley are in full bloom.


The entrance to Nantucket, Massachusetts.

The entrance to Nantucket, Massachusetts.

Nantucket, whose temperatures range from 60 to 70 degrees, is bustling with visitors in the summer as the city hosts many events and comes alive with lush, flower-filled gardens in the summer.

The annual Fourth of July event is a must-see, not only for the fireworks, but also for the farmers market, food trucks and water contest on Main Street between the reserves and the fire department.

In August, the city 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 Nantucket Cottage Hospital at Jetties Beach.

Discover the summer magic in the small towns of Massachusetts

From the Rockport Chamber Music Festival and Ptown's Carnival to the Opera House Cup on Nantucket and the Bridge of Flowers in Shelburne Falls, these Massachusetts towns offer visitors a wealth of fun activities this summer.

Each of these cities is charming, surrounded by natural beauty and welcomes visitors with open arms. So if you're planning your next summer vacation and prefer the tranquility of small-town life, consider visiting these six coolest towns in Massachusetts.

Anna Harden

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