Annisquam Light (circa 1801) Wigwam Point, Lighthouse Road, Gloucester, MA 01930, 978-281-8865, This historic and picturesque lighthouse and its grounds, which include an early Nineteenth Century keepers house, a stone oil house and a garage, is open to visitors and tours; the first lighthouse constructed on the site was built in 1801, while the current lighthouse was completed in 1897.  more...

Beauport, Sleeper-McCann House Museum 75 Eastern Point Boulevard, Gloucester, MA 01930, 978-283-0800, First built as a summer home by Henry Davis Sleeper, a well respected designer and collector during the early part of the Twentieth Century, the house evolved into a sprawling maze of over forty rooms, gables and turrets, and now houses an expansive collection of American and European art and objects that are worth exploring and enjoying, as is the impressive house itself.  

Eastern Point Light (circa 1832) Gloucester Harbor, Eastern Point Boulevard, Gloucester, MA 01930, 978-281-8865, Although the grounds to this lighthouse are currently closed to the public, there is a great vantage point from which to view the historic and scenic structure that is on a spot first established in 1832, with the current lighthouse having been constructed in 1890.  more...

Man at the Wheel Statue Stacey Boulevard, Gloucester, MA 01930, 978-283-1601, Gazing towards the sea with stern look of determination, this statue of a seaman at the wheel represents and pays homage to the maritime history of the Gloucester and Cape Ann area, and bears the inscription "They that go down to the sea in ships, 1623-1923."

Gloucester Lyceum & Sawyer Free Library 2 Dale Avenue, Gloucester, MA 01930, 978-281-9763, Having served the public since 1830, this library features a collection of over one hundred thousand titles and a varied array of programs and cultural events; the library is a great place for research, just finding a good read, or participating in the enjoyable and educational programs and events that are offered.  more... 

Beauport - SPNEA 75 Eastern Point Boulevard, Gloucester, MA 01930, The Sleeper McCann House, 978-283-0800, The Society for the Preservation of New England Antiquities operates over thirty five properties, with houses that span the time periods between the 1600s to the present day, many of which can be toured, and some of which can be rented for special events. With the foremost goal of the society being the preservation of and education about the different historical periods as represented by historic structures, period furnishings and antiques, the organization also features a museum and bookshop, as well as the tours of the various historical properties.  more... 

Cape Ann Historical Museum 27 Pleasant Street, Gloucester, MA 01930, 978-283-0455, This museum displays collections that honour the maritime heritage of the Cape Ann area, as well a great collection of art by regional artists, including the largest collection of paintings ands drawings by Gloucester native Fitz Hugh Lane, who is now recognized as one of the preeminent American painters of the Nineteenth Century; one will also find exhibits of the works of other area artists, decorative arts, antique furniture, and a museum library with archives, photographs, and genealogical records.  

Essex Shipbuilding Museum 66 Main Street, Essex, MA 01929, 978-768-7541, Exhibits, videos and models, hands-on activities. 

Gloucester Maritime Heritage Center 23 Harbor Loop, Gloucester, MA 01930, 978-281-0470, With a variety of programs and exhibits that are both compelling and educational, this center is “the only working historic waterfront in the Northeast” and features such intriguing features as a wooden marine railway, an aquarium, ships and boats that represent the different periods in the evolution of the New England fishing industry, the construction of wooden boats, and an ever changing variety of educational programs and exhibits.  more... 

Hammond Castle Museum 80 Hesperus Avenue, Gloucester, MA 01930, 978-283-2080 or 978-283-7673, This picturesque castle overlooks the ocean, and, besides the interest of the structure itself, features displays of Renaissance art and an organ with eight thousand two hundred pipes.  more... 

North Shore Art Association 197 East Main Street, Gloucester, MA 01930, 978-283-1857, 800-943-2250 (MA only), This museum hosts changing exhibits of great art by some of the best painters, sculptors, and artists in other media; with educational programs, lectures, workshops, classes, events, and other programs, this museum sees its mission as being to promote and educate the public in regard to the variety and importance of American art within the nation’s culture.  more... 

Rocky Neck Art Colony 77 Rocky Neck Avenue, Gloucester, MA 01930, 978-283-4554, The This is the oldest operative art colony in the United States, and boasts more than thirty artists in residence, in a setting that is picturesque and artistically inspiring. 

Schooner Adventure 4 Harbor Loop, Gloucester, MA 01930, 978-281-8079, This National Historic Landmark is the home of Gloucester’s last fishing schooner, and offers interesting and educational on board tours.  more... 

Eastern Point Wildlife Sanctuary Eastern Point Boulevard, Gloucester, MA 01930, 800-AUDUBON, Run under the aegis of the Massachusetts Audubon Society, this wildlife sanctuary protects native wildlife, while offering visitors the chance to commune with nature and perhaps view some of the protected wildlife while walking nature trails. more...

Ravenswood Park Western Avenue, Gloucester, MA 01930, Route 127, 978-526-8687, Depending upon the season, this beautiful six hundred acre forest offers opportunities for walking, hiking, cross country skiing, exploring on snowshoes, and more, in the peaceful setting of this park that includes nearly ten miles of trails and carriage paths.  more...

Anne Rowe Charters Seven Seas Wharf, Gloucester, MA 01930, 978-283-2046, With over thirty years of experience, this charter company specializes in deep sea fishing excursions, especially for Haddock and Cod. more...

Cloud Nine Charters LLC P.O. Box 1112, Gloucester, MA 01931, 978-283-7088, For something a bit different, one can take advantage of the week-long or long weekend cruises that are offered aboard this yacht, where no language other than French is spoken, although passengers need not know French, nor have any sailing experience or knowledge.  more...

Connemara Bay Charters 47 Crafts Road, Gloucester, MA 01930, 978-283-0197, Connemara Bay Charters features both fishing charters for blue fish, haddock, sharks, tuna, cod, striped bass, and more, as well as pleasure charters that include whale watching, sightseeing, family outings, watching firework displays, gathering lobsters, and more.  more... 

Discovery Adventures Sea Kayaking P.O. Box 31, Gloucester, MA 01931, 978-283-3320, 866-KAYAKER, With the goal of offering something for those of all ages and experience levels, Discovery Adventures features kayaking tours and snorkeling on Ipswich Bay, and summer programs that are geared towards children. The guided sea kayaking tours will afford breathtaking scenery, and a feeling of independence and oneness with the ocean and natural surroundings.  more...

Essex River Cruises 5 Dodge Street, Essex, MA 01929, Essex Marina, 978-768-6981, Cruise along scenic Essex River, Hog Island Tour. 

Gloucester Maritime Trail Stage Fort Park Information Center, Gloucester, MA 01930, 978-281-8865, Here, visitors can take advantage of four enjoyable and educational self-guided tours through America’s first seaport.

Harbor Tours Harbor Loop, Roses Wharf, Gloucester, MA 01930, 978-283-1979, This touring company offers island site seeing tours, as well as lobster trap hauling cruises, and more.  more...

Schooner Thomas E. Lannon Seven Seas Wharf, Gloucester, MA 01930, 978-281-6634, Daily sailing excursions into the harbour are offered aboard this beautiful, sixty-five-foot fishing schooner, which include relaxing and scenic two-hour cruises. . more...

Sloop Boat Charters Saint Peter's Square, Gloucester, MA 01930, 978-768-2569, Sloop Boat Charters features sailing and lobster gathering trips aboard an historic fishing sloop.