Maritime Adventure: Gloucester Schooner Festival Highlights
Difficulty
easy
Duration
Full day festival events
Fitness Level
Suitable for most visitors, no special fitness required
Overview
Set sail into maritime history at Gloucester Schooner Festival, where tall ships and old-world sailing come alive with energy and tradition. Discover what makes this coastal event a must-see for adventure-seekers and history lovers alike.
Gloucester Schooner Festival
August 31st, 2025 | $300 per person
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Adventure Photos
About This Adventure
Experience the thrill of the Gloucester Schooner Festival aboard the renowned Schooner Malabar X, a celebrated winner in its class. Join fellow sailing enthusiasts for a day of stunning boat displays and the exciting Mayor’s Cup Race, all while honoring the rich maritime heritage that shaped America.
Gloucester Schooner race onboard the legendary Schooner Malabar X (10) 2024 winner of the medium size Gaff rigged Schooner division and Second only to the Schooner Columbia BOARD AND DISEMBARK AT GLOUCESTER, MA. Gloucester Schooner Festival is a vibrant, informative place for people of like schooning mind to get together and admire one another's traditional boats, before the Annual Gloucester Schooner Festival’s Mayor’s Cup Race. The perfect homage to the sailing industry that built America, come and join us for a Grand Day Out with a trip up to Gloucester and some spectacular boat viewing as we race. Boarding at 9:30am and getting underway for the parade of sail past the Fishermen’s Memorial on our way to the 1pm start of the Mayor's Cup Race off Eastern Point.
Adventure Tips
Arrive early for the best views
Get to the waterfront early to secure a good spot for watching the sailing races and dockside activities.
Bring layers and sun protection
The seaside can be unpredictable—dress in layers and wear sunscreen for a comfortable day outdoors.
Watch the wind conditions
Sailing is wind-dependent, so check weather forecasts and be prepared for changing conditions.
Participate in dockside tours
Join guided tours of the schooners to learn about their history and their crews' skills.
Local Insights
Wildlife
- Seagulls
- Harbor seals
History
Gloucester is known as America's oldest fishing port, dating back to 1623, and has a long-standing tradition of maritime craftsmanship.
Conservation
Efforts are ongoing to preserve Gloucester’s natural harbor and promote sustainable fishing practices to protect local ecosystems.
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Adventure Hotspots in Boston
Frequently Asked Questions
Recommended Gear
Binoculars
Great for viewing distant ships and details up close during the parade.
Sunscreen
Protect your skin while enjoying full sun exposure on the waterfront.
Hat and sunglasses
Shield yourself from the sun and glare during outdoor activities.
Comfortable walking shoes
Explore dock areas and town sites comfortably.