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.
More ways to explore the area's outdoor wonders
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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.
Wildlife
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.
The Gloucester Adventure, Inc.
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.
The Gloucester Adventure, Inc. organizes public sails and festival experiences aboard the Schooner Adventure, a vessel designated as a National Historic Landmark. Operating from Gloucester, Massachusetts, the business presents seasonal sails tied to the Schooner Festival and other maritime events, including the Schooner Challenge public sail and the Schooner Fest Race sail, plus a dedicated Adventure 99th Anniversary Sail.
During Schooner Festival events, passengers can watch local captains compete on an obstacle course, join the Parade of Sail, or witness the Mayor’s Cup Race. The Schooner Fest Race sail includes a continental breakfast and lunch on race day. The anniversary cruise is a 2.5-hour commemorative sail offering lobster rolls, snacks, and drinks, with proceeds supporting vessel preservation efforts.
The Gloucester Adventure, Inc. focuses on showcasing Gloucester Harbor, festival traditions, and maritime history while maintaining clear scheduling and passenger information. The business directs resources toward the Schooner Adventure’s preservation and public programming and encourages visitors to check for updated 2026 schedules for festival and race sails. All trip descriptions and on-board amenities are communicated up front so guests can prepare for weather, photography opportunities, and personal provisions when allowed.
Described itinerary details, meal inclusions for race sails, and the anniversary sail’s 2.5-hour duration are provided in official trip summaries. The Gloucester Adventure, Inc. offers a reliable way to experience historic sailing, competitive festival racing, and milestone celebrations on Gloucester’s waterfront.
Location
Gloucester, MA
Historic New England harbor city
National Landmark
Schooner Adventure
Designated National Historic Landmark
Anniversary Sail
99 years
2.5-hour commemorative anniversary sail
Tours Offered
3 distinct sails
Challenge, Race, Anniversary sails
Check the 2026 schedule for Schooner Festival sails, race participation, and the Adventure 99th Anniversary Sail — spaces fill quickly for festival weekends.
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.
Sunglasses
Protect your eyes from sun glare while on deck.
summer
Waterproof jacket
Stay dry in case of wind or mist.
summer
Sun hat
Shield yourself from sun exposure during the race.
summer
Snacks and water
Keep energy levels up with light refreshments.