Gloucester Schooner Festival – September 2 – 4, 216
Gloucester Harbor
The 32nd annual Gloucester Schooner Festival takes place on Labor Day weekend. It’s Gloucester’s major marine event, with participating vessels coming from ports along the Eastern Seaboard. There are both large and small vessels—ranging from 19 feet to over 125 feet in length. The Mayor’s Race is the signature event of the Schooner Festival and takes place on Sunday, with over 20 large schooners expected to compete. The Schooner Festival also offers plenty of shore side events including Maritime Heritage Day on Saturday and the Parade of Sail on Sunday morning along the Boulevard promenade (Stacy Boulevard, Route 127) as the large schooners head out to sea for the Mayor’s Race. gloucesterschoonerfestival.net
(Photo Credit: Arlene Taliadoros)