Schooner Festival (Labor Day Weekend) Viewing Cruises
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Gloucester Schooner Festival Schedule of Events 2024 Calendar - Cruise Schedule aboard WEJACK to View the Schooners, Schooner Races, Boat Parade of Lights, Gloucester Fireworks, and Parade of Sail
Plan ahead. Purchase tickets below to ensure your spot aboard the Wejack to spectate the following events before they sell out!
How to See the Schooners with Cape Ann Cruises
Join us aboard the legendary Gloucester Fishing Yacht, the Wejack to see all the visiting Schooners up close from the water.
The Wejack has a full bar aboard. We have multiple trips offered daily during the Schooner festival that will be a boatload of fun!
See the Calendar and schedule of events below to learn more about our trips offered for the Schooner Festival.
The Wejack is the perfect spectator boat to get the best views.
Schedule of Events:
Thursday, 09/03/2026
Schooner Challenge Race -5:30-7:30PM
Friday, 09/04/2026
See the Schooners & Scenic Harbor Tour 3:30 PM - 5:00 PM
See the Schooners, Sunset & Scenic Harbor Tour 6:00 PM - 7:30 PM
Saturday, 09/05/2026
Schooner Festival Sunset Scenic Cruise Gloucester Harbor: Departs at 6PM
8PM - Fireworks Cruise Gloucester Harbor - Departs 8:00PM
Sunday, 09/06/2026
Parade of Sail Cruise Departs at 9:30 AM
Mayor’s Cup Race - Departs at 12:30 PM
See the Schooners - Scenic Gloucester Harbor Cruise Departs at 3:30 PM
See the Schooners at Sunset - Departs at 6 PM
Monday, 09/07/2026
See the Schooners - Scenic Gloucester Harbor Cruise Departs at 12 PM
See the Schooners - Scenic Gloucester Harbor Cruise Departs at 3:30 PM
See the Schooners at Sunset - Departs at 6 PM
Plan ahead. Purchase tickets below to ensure your spot aboard the Wejack to spectate the following events before they sell out!
How to See the Schooners with Cape Ann Cruises
Join us aboard the legendary Gloucester Fishing Yacht, the Wejack to see all the visiting Schooners up close from the water.
The Wejack has a full bar aboard. We have multiple trips offered daily during the Schooner festival that will be a boatload of fun!
See the Calendar and schedule of events below to learn more about our trips offered for the Schooner Festival.
The Wejack is the perfect spectator boat to get the best views.
Schedule of Events:
Thursday, 09/03/2026
Schooner Challenge Race -5:30-7:30PM
Friday, 09/04/2026
See the Schooners & Scenic Harbor Tour 3:30 PM - 5:00 PM
See the Schooners, Sunset & Scenic Harbor Tour 6:00 PM - 7:30 PM
Saturday, 09/05/2026
Schooner Festival Sunset Scenic Cruise Gloucester Harbor: Departs at 6PM
8PM - Fireworks Cruise Gloucester Harbor - Departs 8:00PM
Sunday, 09/06/2026
Parade of Sail Cruise Departs at 9:30 AM
Mayor’s Cup Race - Departs at 12:30 PM
See the Schooners - Scenic Gloucester Harbor Cruise Departs at 3:30 PM
See the Schooners at Sunset - Departs at 6 PM
Monday, 09/07/2026
See the Schooners - Scenic Gloucester Harbor Cruise Departs at 12 PM
See the Schooners - Scenic Gloucester Harbor Cruise Departs at 3:30 PM
See the Schooners at Sunset - Departs at 6 PM
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Where is it happening?
63 Rogers Street, Gloucester, MA, United States, Massachusetts 01930
Event Location & Nearby Stays:
Know what’s Happening Next — before everyone else does.
Host or PublisherCape Ann Cruises
