5 Things to See & Do In Gloucester, Massachusetts 

Recognized as the nation’s first port, Gloucester, Massachusetts has so much to offer tourists and visitors all year round. This beautiful coastal city is brimming with history, dining, culture, arts, events, and shopping. There is so much to see and do that you may need several days to fully explore the city and all that it has to offer. 

By land or by sea, touring Gloucester, Massachusetts can be fun, culturally enriching, or relaxing- all dependent upon what you want to see and do. 

Here are 5 things you won’t want to miss if you choose to book a Wolfe Adventure & Tour. 

A Lighthouse Tour 

Discover the fishing and maritime history of Gloucester through the lighthouses that dot the shoreline. The five iconic lighthouses along the rocky shores of Cape Ann are beloved by historians and tourists alike. 

Learn more about Gloucester’s maritime history as you cruise past the Annisquam Harbor Lighthouse (Annisquam Light), Thacher Island Twin Lighthouses (Twin Lights), Straitsmouth Island Lighthouse, Eastern Point Lighthouse, and Ten Pound Island Lighthouse

Explore Rocky Neck Cultural Center 

If you love local art, visiting the Rocky Neck Cultural Center should make the top of your list of stops to make while in Gloucester. 

Take a stroll through the art colony and be amazed at the volume and variety of art all around you! The Rocky Neck Art Colony is one of the oldest working art colonies in the United States and has been established for more than 150 years. 

Not only can you find unique shops to buy paintings, jewelry, sculptures, and other unique gifts, but there are a number of fabulous restaurants in the area and get a good meal with an even better view. 

Head to the Beach 

Need a day of relaxing and enjoying the sun, sand, and surf? Gloucester has a full spectrum of beach choices for you and your tour group. 

Visit Good Harbor, Wingaersheek, Niles, Half Moon, Pavilion, Plum Cove, or Cressy’s Beach. Each one has its own personality and amazing vistas of boats, lighthouses, or surf. Sink your toes in the sand and enjoy a day on the beautiful beaches of Gloucester. 

Go Back in Time 

Gloucester is rich with history and there is no better place to explore than Hammond Castle, a medieval castle along the shoreline of Gloucester. 

Constructed by the eccentric inventor John Hays Hammond in the 1920s, Hammond Castle serves as a beautiful showcase for Hammond’s impressive collection of Roman, Medieval, and Renaissance artifacts.

Visit Downtown Gloucester 

Gloucester is a charming city with plenty of history and culture to explore. The downtown streets allow tourists to explore shops, restaurants, bookstores, galleries, and the iconic Fisherman’s Memorial Statue known as “the Man at the Wheel.” 

Bring your appetite and your camera because this downtown area is filled with tasty treats and vistas of the harbor and ocean! 

If you are interested in booking a tour of Gloucester, Massachusetts or other attractions visit the Wolfe Tours site to find out more about our group tours and excursions.