These 6 Massachusetts Towns Have The Most Unique Festivals

One of America’s most historically significant states, Massachusetts, knows how to throw a party (and not just tea parties!). A key player in the country’s early settlement as well as its fight for independence, the Old Bay State is an awesome place to explore, especially when there’s a festival taking place in one of its attractive small towns.

Whether it’s celebrating centuries-old maritime traditions or a bountiful catch of seafood, this New England state has long embraced festivals as a means of showing the world just how great a place it is to live and visit. Whatever your idea of a good time, there’s a Massachusetts town hosting a celebration just for you.

Salem

Despite its infamous association with the shocking witch trials of 1692 (or perhaps because of it), Salem really is a wonderful place to visit. A pretty coastal community with a flourishing cultural scene, you can find out more about this dark and dangerous period of time at attractions like the Salem Witch Museum and the Peabody Essex Museum. Pedestrian-friendly Essex Street in Downtown Salem also has plenty of references to the infamous trials, with one-of-a-kind shops like Bewitched in Salem selling themed merchandise.

It likely won’t come as a surprise to learn that these eerie happenings have made Halloween a major event in Salem. Throughout October, the Salem Haunted Happenings festival transforms the town into a cross between a carnival and a theme park, complete with a costumed Grand Parade, street performances, and guided ghost tours of famous landmarks connected to the witch trials. The town’s Festival of the Dead runs concurrently and features the much-anticipated Witch’s Halloween Ball at the historic Hawthorne Hotel.

Gloucester

Situated on Cape Ann just 35 miles northeast of Boston, Gloucester’s long-time association with commercial fishing was a feature of the hit film, The Perfect Storm. The town's fishing tradition is commemorated throughout the community, with landmarks like the Gloucester Fishermen’s Memorial, a bronze statue completed in 1925, and the more recent Fishermen’s Wives Memorial paying homage to mariners and their families.

The highlight of Gloucester’s busy social calendar is the St. Peter’s Fiesta. Held in late June, this popular festival celebrates the town’s strong Italian American fishing heritage and was established in the 1920s by Sicilian immigrants. The event kicks off with religious processions and the blessing of the local fishing fleet before the fun kicks into high gear. Festivities include the quirky Greasy Pole Contest where participants attempt to walk across a greased telephone pole extending over the harbor in front of cheering crowds.

Rockport

Located just a few miles from Gloucester on Cape Ann, Rockport is famous as a place to go to in Massachusetts for live music. A revered tradition since 1981, the month-long Rockport Music Festival draws professional musicians and audiences from all over the world with performances at the seaside Shalin Liu Performance Center. This must-attend summer event features a diverse program ranging from classical quartets to contemporary pieces, while off-stage fun includes pre-concert talks and workshops.

The backdrop to this fun festival is the attractive Rockport waterfront. In addition to its wonderful beaches, here you’ll find a stretch of road known as Bearskin Neck. A former fishing wharf and shipping pier, it’s now home to specialty shops and galleries like The Pewter Shop with its unique souvenirs. It’s also where you’ll find the iconic red fishing shack known as Motif No. 1. One of New England’s most photographed (and painted) landmarks, grab a selfie here as you explore the town’s maritime heritage.

North Adams

Set in the scenic Berkshire Hills of western Massachusetts, North Adams is deservedly rated one of the prettiest towns in the state for its wide, tree-lined Main Street. Once a bustling center for industry, the town’s historic commercial buildings and old mills have been repurposed into classy shops, galleries, and attractions. Of the latter, the Massachusetts Museum of Contemporary Art (MASS MoCA) is home to one of the largest centers for contemporary visual art in the United States.

Need an excuse to visit? Shoot for the Solid Sound Festival. Held each summer, this much-anticipated music festival was launched in 2010 by the rock band Wilco and takes place on the MASS MoCA campus. In addition to three days of music, this three-day festival features art installations, comedy shows, and interactive workshops covering alternative and indie music. Taking the kids? The event is known for its family-friendly atmosphere and features activities like learning to play an instrument and magic shows.

Great Barrington

Thanks to its position along the Housatonic River in the southern Berkshires, Great Barrington is a perfect getaway for those wanting to explore some of Massachusetts’ most picturesque countryside. It’s also made a name for itself in the world of cinema, serving as the central hub of the Berkshire International Film Festival (BIFF). Held each spring, this much-anticipated cinematic celebration, celebrating its 19th year in 2025, will again lure established directors and actors from across the country to participate in special screenings and chats.

While much of the action takes place at the historic Mahaiwe Performing Arts Center, documentaries, shorts, and feature films are also screened at other locations around town. Visiting during BIFF also provides an excellent excuse to get out and explore the rest of Great Barrington. Highlights include its attractive downtown with its many independently owned businesses, including great places to stay like The Wainwright Inn Bed & Breakfast.

Provincetown

Set at the very tip of Cape Cod, Provincetown has a long and storied past. Tracing its roots all the way back to the arrival of the Mayflower, try to time your visit to coincide with the Provincetown Carnival. Started in 1978 and celebrating its 47th anniversary in August 2025, this unique festival features a fun parade along Commercial Street complete with costumed participants, colorful floats, live music, and dance routines. Other highlights include sponsored pool parties, boat cruises, and costume balls.

The carnival is also a great excuse to get out and explore other Provincetown attractions. Of these, favorites include the Provincetown Art Association and Museum (PAAM) which often presents exhibits tied to the carnival, as well as the iconic Pilgrim Monument. At a tad over 252 feet in height, this homage to the first pilgrims is credited as the tallest all-granite structure in the country and makes for a stunning photo backdrop.

The Final Word

Together, these six Massachusetts towns undeniably exemplify the state’s fascinating heritage. From maritime traditions in Gloucester and Rockport to Salem’s spooky Halloween festivities, they each attract attention from locals and visitors alike, all looking for a great excuse to let their hair down and celebrate life. Regardless of which festival sparks your curiosity, you’ll find each of these six Massachusetts towns ready and willing to help you party.