Things to do in Gloucester, Massachusetts



Gloucester, Massachusetts is a tourist destination point worthy of any family vacation. I have a series of links below that can be points of interest for you and your family during your stay here. Gloucester is located on Cape Ann, which is basically an island that has a border line that follows the contour of the mainland. We share Cape Ann with the town of Rockport. We have beaches, wonderful restaurants, music venues, galleries, whale watches and schooner cruises in the harbor as well.

Below are some area links that might be of interest to you.

Cape Ann Community Cinema
Independent, art-house, and foreign films at a charming community cinema in Rockport: a short drive from Gloucester.
Cape Ann Chamber of Commerce
Your resource for local businesses, events, and visitor information across Cape Ann and Gloucester.
Discover Gloucester
The official tourism website for Gloucester: guides to dining, beaches, events, and everything to do on Cape Ann.
Gloucester Stage Company
Professional regional theater presenting new and classic American works in an intimate waterfront setting.
Good Morning Gloucester
A beloved daily blog capturing local news, harbor photos, and the everyday spirit of Gloucester life.
Hammond Castle Museum
A dramatic medieval-style castle perched over the Atlantic, built in 1929 by inventor John Hays Hammond Jr.
North Shore Arts Association
One of the oldest and most respected artist associations on the North Shore, with galleries and juried exhibitions.
Rockport Art Association
Historic fine art association in picturesque Rockport showcasing local and regional paintings, sculpture, and prints.
Rocky Neck Art Colony
America's oldest continuously operating art colony, nestled on a scenic Gloucester peninsula with working studios and galleries.
Discover Rockport
The charming neighboring town of Rockport: quaint shops, fresh seafood, and some of the most stunning ocean views on Cape Ann.
Sargent House Museum
An elegant 18th-century Georgian home connected to the ancestors of painter John Singer Sargent, open for tours.
Schooner Adventure
A restored 1926 Gloucester fishing schooner and National Historic Landmark, now open for deck tours and harbor sails.
Schooner Ardelle
A beautifully crafted replica 19th-century cargo schooner offering relaxed harbor and coastal sails out of Essex.
Schooner Thomas E. Lannon
Traditional wooden schooner offering scenic day sails and sunset cruises through Gloucester Harbor and beyond.
St. Peter's Fiesta
Gloucester's beloved annual Italian-American fishing festival each June — featuring the famous Greasy Pole contest over the harbor.
Thacher Island Twin Lights
A remote island with twin historic lighthouses, accessible by boat — ideal for hiking, birding, and spectacular ocean views.
Yankee Fleet Whale Watch
Half-day and full-day whale watches and deep-sea fishing trips departing from Gloucester Harbor, a Cape Ann classic.

© Copyright, all text and images, David Calvo, Calvo Studio, Updated: September 25, 2026