2026 Special Events

Celebrate 100 years of Schooner Adventure with a once-in-a-century lineup of unforgettable centennial sails and waterfront experiences. This summer, we’re honoring a century of Gloucester’s maritime legacy with special events that bring you closer to history, celebration, and the sea itself.

Gloucester Fireworks Sail – July 3rd
Kick off Independence Day weekend in true coastal style aboard Adventure. Step off the dock and into the best seat in the harbor as we sail into an evening of salt air, sunset light, and a front-row view of Gloucester’s spectacular fireworks display over the water. It’s a celebration of community, tradition, and summer on the coast like no other.

Sail Boston Transit Voyage – Gloucester to Boston
Join Adventure as she makes her historic passage to Boston for Sail Boston. Experience the working life of a traditional schooner underway, as we trace the shoreline south in a living connection between ports that have shaped New England’s maritime story for centuries.

Sail Boston Parade of Sail
Be part of maritime history as tall ships from around the world converge in Boston Harbor. Adventure will join the majestic Parade of Sail, offering a rare opportunity to witness and participate in one of the most iconic nautical gatherings in the world—surrounded by a fleet of international sail training vessels and historic ships.

Sail Boston Public Sails
Step aboard Adventure during Sail Boston for public sails that welcome guests to experience wind-powered sailing firsthand. Whether you're a lifelong sailor or setting foot on a tall ship for the first time, these sails offer a hands-on, immersive encounter with maritime heritage in the heart of Boston Harbor.

And More Centennial Experiences All Season Long
From special dockside programming and educational sails to community celebrations and commemorative voyages, our 100th anniversary season is filled with opportunities to connect with the ship, the story, and the sea. Each event is a chance to honor the past while sailing boldly into the next century.

Join us as we celebrate 100 years of Schooner Adventure—where every voyage is history in motion.

2026 Annual Meeting
Feb
4

2026 Annual Meeting

WHAT: Schooner Adventure Annual Meeting
WHEN: Wednesday, February 4th 2026 | 5:30-7:30PM
WHERE: Gloucester Stage | 267 East Main Street

Complimentary nibbles and beverages.

Presentation in the theatre 6:00 PM . . .
Meet our Executive Director Emily Pearce & Board.
A review of our sensational 2025 season.
A taste of what's coming in 2026.
Special thanks, a brief Q&A.

We look forward to seeing you there and celebrating all that is Adventure!

Please register in advance here.

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Descendants Sail
Aug
22

Descendants Sail

Please join us for one of our annual Descendant's Sails, offered FREE to the families of schoonermen. We ask that you share your story with us to be eligible for this sail.
Click BOOK NOW or call 978.281.8079 to make your reservation.

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2026 Annual Meeting
Feb
20

2026 Annual Meeting

WHAT: Schooner Adventure Annual Meeting
WHEN: Wednesday, February 4th 2026 | 5:30-7:30PM
WHERE: Gloucester Stage | 267 East Main Street

Complimentary nibbles and beverages.

Presentation in the theatre 6:15 PM . . .
Meet our Executive Director Emily Pearce & Board.
A review of our sensational 2025 season.
A taste of what's coming in 2026.
Special thanks, a brief Q&A.

We look forward to seeing you there and celebrating all that is Adventure!

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The Codfish Cruise
Aug
10

The Codfish Cruise

The Codfish Cruise is an on board fundraising extravaganza! Enjoy a fun evening at sea and support Schooner Adventure! Look out for your invite as this event is invitation only!

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Tribute Sail
Jul
24

Tribute Sail

Captains Circle Tribute Sail. In honor of the Byrnes, Coolidge, Garland, and Knott families and their contributions to our ship, Adventure,

We will fly your flags that night. We will sail in tribute.

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