Four chances to race in some of New England’s legendary traditional sailing regattas.
You don’t have to be a sailor—or own a boat—to experience the thrill of a real schooner race. The Maine Windjammer Fleet offers several cruises where windjammers participate in some of New England’s most legendary races. These multi-day sailing adventures already offer incredible views, unplugged downtime, and hands-on fun, but race day takes things up a notch.
If you’re feeling active, jump in and help raise the sails or tack the boat as it races across the bay alongside a fleet of historic schooners. Prefer to sit back and take it all in? That’s fine too. Watching these beautiful ships under full sail is an experience in itself. There’s no pressure—just the rhythm of the water, the teamwork on deck, and the quiet satisfaction of taking part in something most people never get to try. It’s a rare chance to be in the heart of maritime tradition, wrapped in a once-in-a-lifetime experience you’ll be talking about long after you’re back on shore.
1. The Great Schooner Race – July 5, 2025 (July 3, 2026)
Available on all Maine Windjammer Association vessels, week of July 4th.
Dubbed “the largest annual gathering of traditional schooners in America,” the Great Schooner Race is a true spectacle—and you can be on deck for every thrilling moment. Held off the coast of Rockland, Maine, this event brings together all the vessels of the Maine Windjammer Association as well as several other Maine schooners. Passengers don’t just watch the race—they’re part of the crew, helping to haul sails, trim lines, and cheer as their boat edges ahead of the fleet. The camaraderie is unmatched, and the competition is friendly but fierce. Book a trip the week of July 4th on any participating windjammer to join the race and visit GreatSchoonerRace.com for more info!
2. Camden Classics Cup – July 25–26, 2025
Race aboard Schooner GRACE BAILEY | Tues, July 22 – Fri, July 26, 2025 or
Windjammer ANGELIQUE | Mon, July 21 – Fri, July 26, 2025
Sail in style during the prestigious Camden Classics Cup, a regatta that brings together some of the most beautiful classic yachts and schooners on the East Coast. This is one of the few times you’ll see traditional windjammers lining up with sleek racing sloops in a dazzling display of wooden hulls and flying sails.
Schooner GRACE BAILEY and Windjammer ANGELIQUE both offer guests the rare chance to crew during this weekend of fast-paced sailing and high-spirited fun. It’s not just a race—it’s an experience steeped in tradition, community, and maritime pride.
3. Eggemoggin Reach Regatta – August 2, 2025
Sail aboard Schooner GRACE BAILEY |Thurs, July 31 – Mon, August 4
This legendary regatta, the largest wooden boat regatta in the world, is beloved by wooden boat enthusiasts for good reason: the setting is stunning, the fleet is world-class, and the sailing is exceptional. Held along the scenic stretch of water between Deer Isle and Brooklin, the Eggemoggin Reach Regatta (ERR) has become a must-do summer event for classic boats.
Schooner GRACE BAILEY takes part in the festivities and welcomes passengers who want to experience what it’s like to race a historic schooner among a fleet of some of the finest wooden boats afloat. From the quiet tension at the starting line to the rush of the finish, it’s a day full of teamwork, tradition, and timeless beauty.
4. Gloucester Schooner Festival & Race – Labor Day Weekend
Race aboard Schooner AMERICAN EAGLE | Wednesday, Aug 27 – Friday, Sept 5, 2025
Each Labor Day weekend, schooners from around New England gather in Gloucester, Massachusetts, to celebrate the city’s rich maritime heritage. The Gloucester Schooner Festival includes a lively parade of sail and culminates in the Mayor’s Race for the historic Esperanto Cup—an exhilarating, close-quarters contest held just outside the harbor.
The Maine Windjammer Schooner AMERICAN EAGLE, a former fishing schooner built in Gloucester in 1930, returns to her port of origin to take part in this legendary event—and you can be aboard for the adventure. As a guest crew member, you’ll help prepare the vessel, raise sail, and take part in a race that honors the working schooners of the past while showcasing their beauty and strength today.
You’ll be sailing alongside other historic vessels like ERNESTINA-MORRISSEY, Schooner ADVENTURE (a former Maine Windjammer), and DENIS SULLIVAN, among many others. In addition to the race, the nine-night voyage includes scenic anchorages along the coast, plenty of time under sail, and an all-you-can-eat beachside lobster bake.
Whether you’re drawn by the friendly rivalry of the Great Schooner Race, the elegance of the Camden Classics, the wooden boat glory of the ERR, or the salty legacy of Gloucester, there’s a schooner race that fits your style. These are more than just sailing trips—they’re immersive, hands-on adventures where you join the crew and become part of something timeless.
Categories: Fleet, Maine Windjammers
Tags: Schooner American Eagle, Schooner Grace Bailey, Schooner Stephen Taber, Windjammer Angelique
