What to know about the upcoming Gloucester Schooner Festival

The 42nd annual Gloucester Schooner Festival is a cherished Cape Ann tradition that began in 1985 as a rendezvous amongst schooners who gathered to race and pay homage to the International Fishermen’s Cup Races of the 1920s and 1930s.

Set for Sept 3-7 this year, this four-day event will feature up to 20 schooners in port who will offer deck tours and charter sails. There will be a Heritage Day event on Saturday, a parade of schooners Sunday along the Gloucester waterfront, and then an offshore race called the Mayor’s Cup.

Hosted by the Maritime Heritage Center, large schooners include the 98-foot Denis Sullivan from Wisconsin, three Maine schooners including the 92-foot American Eagle and the 95-foot Harvey Gamage, and a Massachusetts-based fleet that includes the 110-foot Schooner Ernestina Morrissey from New Bedford, the 122-foot Schooner Adventure from Gloucester, the 92-foot Tabor Boy from Marion, and the 63-foot Adirondack II from Boston, among others.

For the love of racing

“There is no such thing as two schooners getting together without having a race,” said Daisy Nell of Essex, who along with her then husband Scott Edington are the founders of the Gloucester Schooner Festival. “It all began in 1985 when Scott and I bought a schooner named Morning Star. We had just joined the American Schooner Association. They were looking for a place for a rendezvous. So, that first year, we got 20 schooners to come and race. The second year, Gorton’s Fisheries leant us the sterling silver Esperanto Cup trophy which had been stored there since the races ended in the 1930s. We had Nova Scotians who attended and we all played music. It was like a gam – a gathering – and it remains so to this day.”

The International Fishermen’s races of the 1920s and 30s drew tens of thousands of spectators during its heyday. The very last time they were held was in 1938 when Gloucester’s Gertrude L. Thebaud and Canada’s legendary Bluenose drew unprecedented crowds. During that race, an unknown 22-year-old navigator named Sterling Hayden was on the masthead of the Gertrude E. Thebaud of Gloucester. His striking figure captured the attention of the Boston papers with a headline that read “Thebaud Sailor Like Movie Idol.” That exposure led to an acting career and movie contract with Paramount Pictures. It was unfortunately the end of an era for fishing schooners who had already begun the switch to diesel engines and eventually large trawlers for Grand Banks fishing.

“Cape Ann has deep roots as a community connected to the sea, through shipbuilding, fishing, science, art, and countless other trades. The fact that we have so much in our local heritage – with five boats built by Harold Burnham, a living descendent of one of the premier boatbuilding families in Essex. That identity is not simply our history. It is still very much alive here,” said Nell. “Each year, I am particularly excited to bring together people who actually do this work, from fishermen and boatbuilders to maritime organizations and educators, alongside the schooners themselves. You don’t need to buy a schooner ticket to come down, climb aboard, meet people, learn something, and feel part of Gloucester’s maritime story.”

The date of the festival has been set for Labor Day weekend for many years, which is also the weekend of the International Dory Races which will be held simultaneously here.

“It is still amazing to think that what started as a gam amongst some schooner folk in 1985, has become in a sense a place at the forefront of both preserving a tradition, enjoying it in the present and perpetuating it forward so that younger people can grab on for the ride and see where it takes them,” said Dan Albani, executive director of the Maritime Heritage Center. “We are expecting a large crowd, and the maritime heritage center is also one of the best places to view the whole harbor.”

Taking command

For Gloucester native and captain Tyler King, 29, who owns and operates the schooner American Eagle of Rockland, Maine, returning for schooner festival is one of the things he looks forward to most each year.

Tyler grew up working at his parents’ Gloucester boatyard River Boat Works. It began in 1904 as Montgomery Boat Yard on the Annisquam River. The boatyard is a treasure, and most recently it served as a backdrop in scenes from the popular Apple TV- series Widows Bay starring Matthew Rhys because of its authenticity.

King grew up attending the Gloucester Schooner Festivals and held onto a dream of becoming a schooner captain. He got his schooner experience in Maine, and by 2022 at the age of 25, following decades of stewardship by Captain John Foss, King took ownership of this 1930s Gloucester-built schooner American Eagle, which is recognized as a National Historic Landmark.

“I chose to do this and followed this dream as I felt I could connect our maritime past to the present. The racing and the parade on Sunday are all part of the fun and it is always fantastic. Whenever Gloucester has a festival they make it special and it gives all of us an amazing platform to show people that this is something that is both a part of our past, present and will hopefully live on in the future. We are here trying to preserve it.”

Apprenticeships and opportunities

There are countless young people who have benefited from the tireless effort by both the non-profits and charter businesses to preserve, protect and promote the maritime trades on Cape Ann.

“We hire seven to ten people as crew every summer. Typically, they are in their early twenties and although they are not all green hands, everyone learns on the job. We are considered a great vessel for people to gain experience,” said Capt. Greg Bover of the Schooner Adventure, which is celebrating its 100th year. “Some crew members get jobs on schooners that are heading south for the winter, to places like the Caribbean or Florida.”

Bover is the president of the non-profit Schooner Adventure board and one of hundreds of dedicated volunteers that sail and maintain the vessel. After working 42 years as a skilled carpenter building organs for the Fish Organ Company in West Gloucester, he pursued his 100-ton license and became a volunteer carpenter and captain on the Schooner Adventure. Along the way, Bover has imparted his carpentry skills to many more volunteers who maintain the boat.

Along with the schooners and learning opportunities there, both the Maritime Heritage Center and the Essex Shipbuilding Museum have seen how apprenticeships are one way to keep younger people interested in the maritime trades and encourage them.

Courtney John Andersen, from California, who will be joining the fun at schooner festival, remains one of a handful of master riggers working in the field today. For the month of September, he will be working on the rigging of the replica tall ship Friendship of Salem.

“I started out as a college student working on the replica of the ship Bounty when it was in Florida. I became a master rigger on the Bounty, as currently there are no schools or programs to teach this,” Andersen said. “It has been an amazing career for me. Because of my skills, I was hired to do five Pirates of the Caribbean films as a master rigger. I continue to get work in Hollywood having done traditional rigging for films and television.”

The Essex Shipbuilding Museum is also proud of that fact that traditional shipbuilding is ongoing in Essex, and “we are still adding chapters to that story,” said KD Montgomery, 33, executive director of the Essex Shipbuilding Museum and co-sponsor of Heritage Days.

“Harold Burnham [who most recently built the Schooner Ardelle] is obviously a giant part of that continuation, but Harold’s story is itself the continuation of hundreds of years of people teaching one another. I see smaller versions of that everywhere. Our boatbuilder, Jeff Lane, is a wonderful example. We have photographs of Jeff as a little kid here. Today he is the person passing those skills along to nearly every young person who comes through one of our educational programs,” said Montgomery. “There is also Zack Teal, who helped build the schooner Ardelle and now runs tugboats in Boston Harbor.”

“Shipbuilding is wonderfully multidisciplinary. Our students meet everyone who touches the process, from the arborists who take down the trees we build into boats, to boatbuilders, mechanics, fishermen, and mariners,” Montgomery notes. “They get a taste of many different skills and build relationships with people who can vouch for them when they head out looking for work.”

More information on the Gloucester Schooner Festival can be found here.