Water Activities & Historic Sailing with The Gloucester Adventure, Inc.
Difficulty
moderate
Duration
2–3 hours
Fitness Level
Participants should have basic swimming ability and general physical fitness to handle active sailing conditions.
Overview
Set against Gloucester’s rugged coast, the 2025 Schooner Challenge delivers a high-energy maritime race aboard the historic Schooner Adventure. Perfect for sailing enthusiasts or anyone seeking a thrilling day on the water, this event blends history, competition, and stunning seaside scenery.
2026 Schooner Challenge Public Sail! Check back for 2026 schedule.
For All Ages • 2.5 Hours • Celebrate in Style on a Historical Landmark! A Gloucester Tradition!
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About This Adventure
Experience the thrill of the Schooner Festival aboard the historic Schooner Adventure! Watch local captains showcase their skills in a friendly competition while navigating an exciting obstacle course. Enjoy the vibrant atmosphere, capture memorable moments, and bring your favorite snacks and drinks for a perfect Labor Day Weekend tradition.
Very popular Labor Day Weekend tradition!
Duration and Departure Location
2Hours ***IMPORTANT! Departure location is the I4C2 Pier located behind the Gloucester House/Blue Collar Lobster 63 Rogers Street.
About
Sail aboard Schooner Adventure during Schooner Festival weekend! Join our local Schooner Captains as they participate in a friendly competition putting their seamanship to the test over an "obstacle" course to win the coveted Rum Bottle Award. Visiting schooners already arrived will join the event.
What to Bring
Snacks, beverages, and your camera!
Adventure Tips
Wear layered clothing
Weather on the water can change quickly—bring layers to stay comfortable throughout the day.
Bring your camera
Capture the excitement of the race and scenic coastal views from onboard.
Arrive early
Secure your spot early for the best views and to get a good vantage point.
Secure personal belongings
Keep valuables stored safely to enjoy the adventure without worry.
Local Insights
Wildlife
- Seals
- Humpback whales
History
Gloucester has been a major fishing port since the 1600s, making its sailing events deeply rooted in maritime tradition.
Conservation
The schooner race promotes local maritime heritage and encourages sustainable tourism practices in this sensitive coastal environment.
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Adventure Hotspots in Boston
Frequently Asked Questions
Recommended Gear
Sunglasses
Protect your eyes from the sun's glare reflected off the water.
summer specific
Sunscreen
Prevent sunburn during prolonged exposure on deck.
summer specific
Hat with brim
Shield your face from sun and wind while on deck.
spring;summer;fall specific
Waterproof jacket
Stay dry and warm if the weather turns or during less sunny days.
spring;fall;winter specific