Things To Do In Rockport, MA

Rockport is a small seaside community located directly east of Gloucester on the tip of Cape Ann. Surrounded on three sides by the Atlantic, Rockport is home to many distinctive beaches and scenic vistas that have made the town popular with artists and photographers. Unlike many small towns that border larger cities, Rockport possesses its own unique culture that separates it from Gloucester. 


Though small in both area and population, Rockport is filled with places to explore and hidden gems to discover. Bearskin Neck, a thin outcrop of land stretching out from the mainland into the Atlantic, is the cultural heart of Rockport. Originally, Bearskin Neck solely consisted of various lobstermen’s and fishermen’s shacks, but over time many different shops, art galleries, and restaurants opened, making the Neck one of the most beautiful and distinct shopping areas in Massachusetts. The end of the neck transitions into a rocky outcropping, which offers amazing views of Sandy Bay and downtown Rockport.

Motif No 1 in Rockport Harbor

Rockport has a long history as an art colony, and is home to over 30 art galleries, including the Rockport Art Association & Museum. For nearly a century, artists have flocked to Cape Ann’s rugged coast to paint “en plein air” (out of doors). Motif No. 1, once a humble fishing shack, is commonly considered the most often-painted building in America.

Inside the Shalin Liu Performance Center. Photo © Rockport Music.

In addition to visual arts, Rockport is also a music-lovers paradise, with concerts of all types taking place throughout the year. The Shalin Liu Performance Center is the spectacular home of Rockport Music, an organization that brings work-class performances of classical, jazz, pop, folk, and world music to Cape Ann. Rockport Music hosts two major summer festivals, the Rockport Chamber Music Festival and the Rockport Jazz Festival

Halibut Point State Park.

While the town is primarily known for its arts culture and its beaches, nature lovers won’t want to leave once they begin to experience Rockport’s wide array of parks, quarries, and forested walking trails. Adventurers will love hiking through the woods to one of Rockport’s swimmable quarries, which boast warm, calm waters and great swimming. Halibut Point State Park, formerly the Babson Farm granite quarry, does not allow swimming but instead offers sweeping and dramatic views of the Atlantic, including coastal New Hampshire and Maine. Tours are available on Saturdays in the summer, or you can walk on your own over the 2.5 miles of trails.


Long Beach in Rockport.

A Rockport vacation is incomplete without a trip to Long Beach. Boasting a mile-long stretch of sandy coast, Long Beach is one of the best beach vacation spots for everything from relaxing with a good book to starting an impromptu game of catch or Frisbee. Long Beach offers up some of the most scenic panoramas on Cape Ann, including views of Thacher Island’s famous twin lighthouses on the horizon. Front Beach and Back Beach are both accessible from the heart of downtown Rockport, while Cape Hedge BeachFolly CovePebble Beach, and Old Garden Beach are smaller neighborhood beaches.

Whether you’re looking to reconnect with the sea and with nature, explore a quintessential small New England fishing town, or simply looking for some quiet relaxation time, Rockport can provide it. With its perfect blend of modern conveniences and rustic charm, you will feel right at home in this little town at the edge of Cape Ann. No matter your age, background, or interests, you will find something to love about Rockport. 


Traveling around Rockport is made easy with the Cape Ann Transportation Authority’s (CATA) Rockport Shuttle. This service is operating for the 2021 season from July 2 through mid–October from the Rockport Park N Ride lot (2 Blue Gate Lane) to Downtown Rockport every 20 minutes. For additional shuttle service information, download the PDF.

Looking for things to do in Rockport MA on a budget? Check out our blog post, 25 Free Things To Do On And Around Cape Ann This Summer.

If you are looking for where to stay in Rockport, MA? Look no further!

Call our Guest Experience Specialists toll-free at (855) 969-2775 or book your vacation rental stay online.