If crystal-clear beaches, delicious seafood, schooners, and history sound of interest to you, a trip to Gloucester, Massachusetts is a must. The coastal village turned city is a New England gem, but not as widely known as other coastal favorites like the Cape and Islands.
Located on Massachusetts’ North Shore, Gloucester is only 1 hour away from Boston, and accessible via the MBTA Commuter Rail from North Station. Settled in 1623 and formally established in 1642, Gloucester became America’s first seaport, making it the oldest today. The maritime and fishing culture of Gloucester remains prosperous and omnipresent to this day.
History of Gloucester, Massachusetts
The Pawtucket people inhabited what is now modern day Gloucester. They are part of the Northeast’s Algonquin-speaking tribes.
In 1623, The Dorchester Company sent 14 fishermen to Cape Ann to establishing a fishing outpost. In 1642 the town incorporated on Massachusetts Bay Colony. What started as small boat fishing evolved into an industrial schooner fishing fleet, turning Gloucester into the “fishing capital of the world” by the early 20th century.
To celebrate its history, now in its 42nd season, Maritime Charters hosts the Gloucester Schooner Festival, where over 40 ships take to sea! The event coincides with Labor Day Weekend.
Things to do in Gloucester
The maritime city offers an idyllic New England coastal village feel with just about every water activity you can imagine—from pristine beaches to boat rides. Board a ship handmade by multi-generation shipbuilders with Maritime Gloucester. Take a trip with Cape Ann Whale Watch for a chance to spot breaching whales!
Explore the 42 markers on Gloucester HarborWalk to learn about the city’s maritime history while enjoying scenic views of the water and parks. Hammond Castle boasts 100 years of history inside the picturesque medieval-style castle.
Gloucester Beaches
There are four main beaches in Gloucester, along with several other lesser-known beaches, each offering something unique. Wingaersheek is known for its tidal pools that form around large boulders and create clear “Caribbean-like” pools. Good Harbor Beach is the closest widespread beach to the Commuter Rail with clear waters and a small island in the distance. Nearby, Long Beach, is as the name suggests. Although it’s technically in Rockport, the beach is beloved by both towns for its long stretch and waves for surfing and boogie boarding. At the base of Stage Fort Park is a hidden beach, although small the views are spectacular and it’s incredibly close to the Commuter Rail.
Where to eat in Gloucester
As America’s oldest Seaport, Gloucester offers some of the best seafood in New England! You can’t go wrong with any of the seafood spots, but Causeway Restaurant draws crowds for its jumbo portions of fresh seafood. Sushi Sang Lee offers an alternative way to enjoy incredibly fresh seafood in an elevated setting.
If you’re called to land, Short & Main fires some of the best pizza in the state, with unique combos and incredible dough. In the daytime, stop by Source Bakery for sandwiches, pastries, and artisanal coffee. Holy Cow’s nationally-recognized ice cream in over 20 creative flavors is the cherry on top of a day in Gloucester.
Getting there from Boston
Gloucester is just 45 minutes north of Boston by car or 1 hour by train. If traveling by train, take the Rockport line that travels daily from North Station to the Gloucester stop.
