Sailing Adventure in Gloucester at Schooner Fest Race
Difficulty
moderate
Duration
Full day (approximately 6-8 hours)
Fitness Level
Participants should be comfortable on a boat and able to handle mild physical activity.
Overview
Join an exhilarating schooner race in Gloucester, a town renowned for its maritime history. Experience racing aboard the schooner Adventure and enjoy stunning coastal views—all part of the iconic Schooner Fest.
2026 Schooner Fest Race Sail! Check back for 2026 schedule.
For All Ages • 6 Hours • The Ultimate Sailing Experience aboard Gloucester's Flagship!
Select participants and date
About This Adventure
Experience the thrill of the Parade of Sail and the Mayor's Cup Race aboard the Schooner Adventure! Enjoy a full day of exhilarating racing, complete with a continental breakfast and lunch. Witness the stunning sights of Gloucester from the deck, making unforgettable memories in this cherished Labor Day tradition.
Come aboard for the Parade of Sail & Mayor's Cup Race!
A Labor Day Weekend Tradition. Check back for 2025 details.
Duration and Departure Location
6 Hours IMPORTANT! Departure location is the I4C2 Pier located behind the Gloucester House 63 Rogers Street.
About
Join Schooner Adventure's Captain and Crew in the Parade of Sail and then the exciting Mayor's Cup Race. This is a full day of invigorating racing and includes a continental breakfast and a full lunch and beverages. There is no finer way to take in the glorious spectacle of this landmark Gloucester event than from the deck of Adventure! (no alcoholic beverages are allowed on this sail)
What to Bring
Sunglasses, a hat, binoculars and your camera!
Adventure Tips
Arrive early on race day
Get a good vantage point and avoid missing the start of the race.
Dress for the weather
Wear layered clothing and bring sun protection for a full day on the water.
Bring a camera
Capture the action and scenic views from the deck or nearby shoreline.
Stay hydrated
Bring plenty of water, especially if the weather is warm.
Local Insights
Wildlife
- Seagulls
- Humpback whales (seasonal migrations)
History
Gloucester has been a major fishing port since the 17th century, and its maritime culture remains central to the town’s identity.
Conservation
The event emphasizes responsible sailing practices and promotes environmental awareness to protect Gloucester’s coastal ecosystem.
Select participants and date
Adventure Hotspots in Boston
Frequently Asked Questions
Recommended Gear
Sunglasses
Protect your eyes from sun glare while on deck.
summer specific
Waterproof jacket
Stay dry in case of wind or mist.
summer specific
Sun hat
Shield yourself from sun exposure during the race.
summer specific
Snacks and water
Keep energy levels up with light refreshments.