History

Note: Due to the weather, these events have been postponed to Labor Day Monday. The Mayor's Race is a major part of the Gloucester Schooner Festival 2025, where participating schooners in the weekend activities compete for for the Esperanto Cup, Ned Cameron Trophy and Betty Ramsey Trophy off Eastern Point and East Gloucester.

Come for guided tours of the Burgess Aviation Museum! Tours feature photographs, artifacts, and a diorama celebrating the 1910 flying field at Plum Island in Newbury – New England’s first – and the current Plum Island Airport. From April to August 1910, Marblehead yacht builder W. Starling Burgess conducted a series of increasingly successful test flights on biplanes he designed and built.

Schooner Ardelle invites you on a unique adventure on the coast of the North Shore!  Board the Ardelle as we depart the Sail Boston festival and sail back to Gloucester in company of the fleet of Tall Ships participating in the Tall Ships Challenge/Redez-vous Tall Ships Regatta race from Massachusetts to Canada. We will return to Gloucester in the afternoon, prior to the race start. Tickets are also available to join the Ardelle to watch the start of the tall ships regatta that afternoon! Passengers are responsible for arranging their own transportation to Boston and out of Gloucester. Trunnel tickets and Vouchers are not valid for this unique sailing experience.

Step back in time and be inspired by the nightscape at a 17th century saltwater farm. Stroll through the house, lit by candlelight, and imagine life in colonial days. This Open House is offered in conjunction with Ipswich is First...Period, a community celebration of 17th century architecture, and an homage to hearth, home and the celebration of Thanksgiving. A quartet will fill the halls with period music.