Can’t-Miss Events at This Year’s Gloucester Schooner Festival

July 29, 2025 / A Local Favorite, History/Maritime, Things to Do & See

Every Labor Day weekend, Gloucester, Massachusetts transforms into a bustling celebration of maritime history, community spirit, and—of course—majestic schooners. Now in its 41st year, the Gloucester Schooner Festival returns from Wednesday, August 27 to Sunday, August 31, 2025, bringing with it a full slate of family-friendly events, sailing opportunities, and more.

Whether you’re a seasoned festival-goer or planning your first visit, here are five must-do experiences to make the most of this iconic Cape Ann tradition:

Tour Local and Visiting Schooners

Friday, August 29 & Saturday, August 30
Get an up-close look at the schooners docked around Gloucester Harbor. Many vessels (like Schooner Adventure above) open their decks to the public, giving you a chance to meet the crew, learn about the ship’s history, and take in the craftsmanship that keeps these tall ships sailing year after year.

Check the full event schedule on MaritimeGloucester.org to find schooners offering deck tours over the weekend.

Set Sail on a Schooner

Public Sails Throughout the Weekend | Booking Required
There’s nothing like the feeling of the wind in your hair and the sound of sails as you cruise Gloucester’s historic harbor. Choose from public sails, chartered cruises, or even book a spot aboard a schooner participating in a Schooner Challenge.

Visit MaritimeGloucester.org for a list of schooners offering sails throughout the festival.

Celebrate Maritime Heritage Day

Saturday, August 30 
Head to Maritime Gloucester for a full day of hands-on activities, demonstrations, and exhibits that celebrate Cape Ann’s connection to the sea. Enjoy food trucks, music, kid-friendly fun, and maritime displays along the working waterfront.

Don’t forget to check out the touch tanks and historic exhibits while you’re there! Indoor and outdoor touch tanks offer a closer look at local marine life, and additional exhibits showcase the history of schooner building, the Marine Railway, and more.

Additional vendors, events, and deck tours will be taking place at I4C2. Find the full schedule for Maritime Heritage Day here.

Watch the Parade of Schooners

Sunday, August 31 
Cap off your festival experience with the awe-inspiring Parade of Sail, when the schooners make their grand procession through Gloucester Harbor before participating annual schooner races. The best viewing spots are along Stacey Boulevard or at Stage Fort Park.

Bring a chair, pack some snacks, and soak up one of Gloucester’s most unforgettable summer sights.

Whether you’re in it for the history, the sailing, or just the scenic views, Gloucester Schooner Festival is the perfect way to say goodbye to summer. From dockside events to high-seas adventures, there’s something for everyone.

View the full event schedule at MaritimeGloucester.org and find everything you need to plan your visit here.