Catch the Maritime Magic of Gloucester Schooner Festival

May 20, 2024 / History/Maritime

In the heart of the North Shore’s summer calendar stands a maritime tradition that has shone for four glorious decades – the Gloucester Schooner Festival. This cherished event paints a vivid picture of wood, canvas, and water against the rugged coastline and seasoned docks of historic Gloucester Harbor. More vibrant than ever, it pays tribute to the legacy of Gloucester’s schooner fleet.

Gloucester Schooner Festival - Gloucester MA - Discover Gloucester

Setting Sail: The Festival’s Inception

The festival’s origins trace back to June 1985 when Gloucester Harbor transformed into a sea of sails after the American Schooner Association invited the Nova Scotia Schooner Association to a rendezvous. Daisy Nell Collinson, the festival’s beloved chair, fondly reminisces about the inaugural event: “We had a bagpiper onboard Morning Star, to pipe our way out of the harbor. Also aboard was an artist named Bob Prouty, and my miniature dachshund named Moose. Bob Prouty had offered an original oil painting of the winning schooner, as a first prize. The winner was a Nova Scotia schooner named Fortune receiving the finished piece at the evening’s gala event.”

Event excitement led to the formation of a committee, and under the leadership of Mike Costello and the Cape Ann Chamber, the Gloucester Schooner Festival became a Labor Day tradition.

Gloucester Schooner Festival

History on Display

The festival expanded in 1986 with the introduction of the Mayor’s Cup Race, featuring a sterling silver replica of the 1920 Esperanto Cup donated by Gorton’s of Gloucester. In a spirited 2.5-mile race, iconic schooners like Pilot, Spirit of Massachusetts, and Ernestina-Morrissey battled for glory. Captain John Wigglesworth, steering Pilot to victory, expressed “This was a big win for the great old Pilot. I hope this first victory is the beginning of the big schooners return to Gloucester – their birthplace.”

Gloucester’s schooner fleet has been well represented throughout the festival’s history. Adventure, Roseway, and American Eagle, former fishing vessels, receive thunderous applause from the crowds.

Special appearances by many legends like Bluenose II, Ernestina-Morrissey, Pride of Baltimore II, Spirit of Bermuda, Virginia and many others heighten the festival atmosphere annually. The launch of Columbia in 2015, a steel replica of the iconic Gloucester racing fisherman, saw the creation of the Columbia Trophy in 2016.

Medium-sized and smaller vessels like When & If, Brilliant, Alert, and Tyrone challenge their larger counterparts, providing thrills for festival fans. Local heroes Thomas E. Lannon and Ardelle reflect Gloucester’s fishing fleet. With the addition of Isabella in 2023, five vessels at the Festival were built by local legend, Harold Burnham, preserving a centuries’ old legacy of Essex-built, Gloucester-fished schooners. The festival features numerous privately-owned vessels, essential for celebrating our shared heritage. They’re integral to the festival experience!

The Thomas E Lannon Schooner

An Unconventional Win

In 2001, Ernestina-Morrissey clinched victory in an unconventional manner. With no wind, the race committee ruled that the first schooner to cross the start line would win. Captain Madeira recalls the moment: “With little wind and our boat drifting backwards, I allowed the crew to go fishing. In the slow pace, I discussed with two mischievous crew members the idea of putting a dory in the water. Finding no rule against it, they rowed the 19th-century schooner over the line, employing what old-timers called a ‘Nova Scotia tow.’ Many competitors were left shaking their heads for not having thought of it themselves.”

Legacy and Horizon: Celebrating 40 Years

The Gloucester Schooner Festival’s enduring popularity is a testament to its profound cultural connection with the city. Celebrating its 40th year, now at Maritime Gloucester, an educational non-profit preserving Gloucester’s working waterfront, it hosts thousands of visitors with deck tours, sailing, charters, demonstrations, food, fun and exhibits. Saturday’s Maritime Heritage Day and Sunday morning’s Parade of Schooners along the Boulevard are spectacles not to be missed.

We invite you to embark on an unforgettable experience at this year’s Gloucester Schooner Festival, where the sea whispers tales of the past, and the wind carries promises of a maritime future. Join us this Labor Day in celebrating the resilient spirit of Gloucester and the timeless allure of its beloved schooners legacy.