Set Sail at Gloucester’s Schooner Festival

August 15, 2023 / History/Maritime, Outdoor Adventures, Things to Do & See

Labor Day weekend is often considered synonymous with the end of summer along with the carefree days and nights accompanying this much-treasured New England season. In Gloucester and throughout Cape Ann, Labor Day weekend is also associated with a festival that attracts thousands of visitors looking for one last hurrah before summer is declared over – the annual Gloucester Schooner Festival

This year marks the 39th annual Schooner Festival since its inaugural weekend in 1985. Back then it was a 3-day rendezvous between American and Nova Scotian Schooner Associations. Held every year since its inception over the Labor Day weekend, this festival celebrates the maritime and cultural history of the city and offers family-friendly activities such as the magnificence of the Parade of Sails, the competitive action of Dory Races, as well as live music, food, and fireworks. 

Let’s take a closer look at the jam-packed schedule of events for the 2023 Schooner Fest as well as a peek at which schooners visitors will be able to tour, set sail on, and enjoy watching in the Parade of Sail. 

A Little History Behind Gloucester’s Schooner Fest

It wouldn’t be a festival without an interesting backstory of how these fun-filled events began. The origins of Gloucester’s Schooner Festival take us back to the 1920s and the International Fishermen’s Races. Sailing enthusiasts from across the globe followed this particular series of races as fervently as the America’s Cup is followed today. 

The initial races came in the form of a friendly competition and an invitation from Gloucester’s sister city in Nova Scotia. Sailors from Lunenburg, Nova Scotia raced for years against Gloucester’s “racing fishermen.” During the inaugural races Gloucester came out victorious but in subsequent years until 1930, the Bluenose of Nova Scotia would win consistently. 

Although the days of formal racing between these two formidable competitors are over, the Schooner Festival is a nod to the races of the past and a way of honoring the legacy of these races and vessels. 

Every year, hosted by Maritime Gloucester, the Mayor’s Races for the Esperanto Cup & the Columbia Trophy are held. Additionally, there are the incredibly popular Maritime Heritage Day deck tours and sailing trips aboard these sleek vessels. Visitors love the races, Boat Parade of Lights, fireworks, concerts, live entertainment, and of course the local cuisine! 

Participating 2023 Schooners 

Over the years, the Gloucester Schooner Festival has become an internationally recognized maritime and sailing event. Here are a handful of the more than 20 schooners you can expect to see including where they will be docked along the piers in Gloucester Harbor. There will be ample opportunities to tour the decks, set sail, or watch as they join in the Parade of Sail. 

    • Ernestina Morrisey, Massachusetts Flagship at the Maritime Gloucester Pier
    • Ardelle at the Maritime Gloucester Pier
    • Thomas E. Lannon at Seven Seas Wharf near I4C2
    • Bald Eagle Mooring 
    • Isabella at Maritime Gloucester Pier
    • Adventure at the I4C2 Schooner Docks
    • Denis Sullivan at the I4C2 Schooner Docks
    • Alert at the I4C2 Schooner Docks
    • Redbird Mooring

Visitors can get a personal and up-close experience with these magnificent vessels however they choose. Learn the history of the schooner with a deck tour aboard several of the vessels, or buy a ticket and get aboard for the thrill of open sail aboard these fantastic fishing schooners in historic Gloucester Harbor. 

Schooner Festival Events 

Starting Thursday, August 31st, and running through the holiday weekend until Monday, September 4th, Gloucester’s Harbor becomes a hub of activities including vendors with food trucks, local merchants’ cuisine, live entertainment, and activities that center around the magnificent schooners on display. 

Schooner Deck Tours 

If you’ve never had the chance to step aboard a majestic schooner, now is the time. Talk to the crew, get a feel for the wheel, and check out the features that you will only find on one of these beauties. To find out more about this free opportunity to experience what it’s like on a schooner visit Maritime Gloucester Schooner Festival

International Dory Races 

Steeped in tradition and fun competition, the International Dory Races are a legacy race similar to the International Fisherman’s Races. Ongoing for 71 years, this competition between Lunenburg, Nova Scotia and Gloucester rowers is a mid-summer phenomenon. 

Celebrating this epic shared history, Gloucester Schooner Festival hosts the Gloucester International Dory Racing Committee for the past several years, putting on a schooner crew dory race exhibition. Schooner crews and local participants can try their hand at racing against and with the “pros” of our mighty Gloucester rowers. For specific times and locations to best view the races visit Maritime Gloucester Dory Races

Maritime Heritage Day 

The land-based heart of Gloucester Schooner Festival is Maritime Heritage Day at Maritime Gloucester. This free-to-the-public day as part of the Schooner Festival allows visitors to tour schooners, explore Maritime Gloucester’s museum, and soak up Gloucester’s rich maritime heritage. 

Starting with the Dory Exhibition Races in the morning, visitors can enjoy a full day of salty demonstrations, hardy stories, fantastic activities, curated food-truck experiences, and real hands-on fun. March with the Constitution Marines, filet a fish, check out our touch tanks, learn how to make and mend nets, explore the ocean floor with an ROV sub, make rope, learn your knots, the list of fun goes on and on. 

Boat Parade of Lights 

Starting on the Annisquam River, the Boat Parade of Lights is a must-see event as each boat is uniquely decorated and proud to show off its creative side. This local fan favorite is a great beginning to a night of harbor lights with the Fireworks later in the night. Best place to watch?  You guessed it; the deck of a schooner!

Parade of Sail 

Historic Gloucester Harbor comes alive with sails once again! This awe-inspiring event will have you reaching for your camera! Schooners proceed from Gloucester’s Inner Harbor, past the Fisherman’s Memorial on Stacy Boulevard, to the race starting area off Eastern Point.

Mayor Races for the Esperanto Cup 

Immediately following the Parade of Sails, the schooners line up off Eastern Point to begin the Mayor Races for the Esperanto Cup. As a nod to the International Fishing Schooner Races of the 1920s and ’30s these Mayor Races are a sight to behold.

In addition to these events, there will be live music along Stacy Boulevard, an evening of fireworks, and food trucks to keep visitors entertained.