Nautical historians will tell you Swampscott is best known as the New England town where the fishing dory and the lobster pot were invented.

But over the past half century, while fish stocks dwindled, the town’s interest in recreational sailing continued to grow.On June 23, the town celebrated the 50th anniversary of its sailing program, which today is run by the Recreation Department, supported by the Friends of Swampscott Sailing, and includes a close association with Swampscott High School’s Big Blue Sailing Team.

Big Blue sailors train at Marblehead’s Pleon Yacht Club because the facility isn’t affected by the tide, unlike the Swampscott Yacht Club headquartered in the historic Fish House on Fisherman’s Beach.

According to Recreation Department Director Danielle Strauss, several Big Blue sailors have gone on to sail for Tufts University and Roger Williams University. “We live on the water, so my motto is: Give your kids the gift of sailing,” she said.

Chris Callahan shows Pam Rotner how to rig the sails.

The anniversary party on the town’s waterfront served as a reunion celebration for those who learned to sail in Swampscott. The crowd included those who served as directors and instructors during the program’s early days.

The late David Shepherd was the program’s first instructor. Former student Christopher Callahan recalled him fondly. “The Swampscott Sailing Program was, and indirectly is, still a big part of my life. I was in the first sailing class in 1967 with Director David Shepherd. We had two, and sometimes three students in the old Optimist prams – usually sitting in a few inches of water. It was my introduction to sailing and boats – standing in the tippy boat to rig the spritsail, rainy days poring over the fascinating nautical charts in the attic of the old Fish House surrounded by ancient fishing gear.”

Callahan, who later crewed aboard the tall ship Pride of Baltimore, chuckled at one particular memory. “We were sailing in the harbor when a sudden fog rolled in. Slipping the attention of the director, we sailed as fast as we could toward where we hoped Egg Rock would be. When the fog lifted, he chased us down in the Boston Whaler and he was not happy, but I was bitten by the bug of a sea adventure.”

Swampscott Recreations Commission Sailing instructors and friends: (L to R) Instructors Eileen Kain, Sally McIntosh, Robin Lougee and Director Chris Callahan. Back row: Neil Snow, Scott Torrey and Mary Callahan.

Win Quayle was director in 1974-75. Callahan was assistant and took over as director in 1976-77, along with assistants Sally McIntosh, Robin Louges and Eileen Kain.  

“Sally was a student, then intern, then assistant director and jack of all trades,” he said, describing McIntosh as the face and spirit of Swampscott sailing from 1970 to 1980.  “The program would not have been the same without her dedication.”

Through the years, students have learned to sail a variety of boats – prams, Widgeons, Americans, 420s, Optimists, and occasionally larger sloops. 

From left to right, Calla Walker, David Nussbaum and Cathy Bisegna receive instruction before sailing off in one of the town’s Widgeons.

Steve Eckman, founder of the Friends group, recently reached out to David Shepherd’s twin brother, Edward, to hear a few sailing stories. He learned that David Shepherd was a history buff and named boats in the inaugural pram fleet after British Navy ships that fought in the Battle of Trafalgar.  A creative instructor, Shepherd also taught 17th-century battle tactics, barking commands at students to help hone their skills.

Former student Nancy (Olson) Tamez was awarded the Francis J. Cassidy Trophy in 1970 for best overall sailor in a ceremony on Fisherman’s Beach. “Undoubtedly my fondest memory,” she said. “What a fun time.”

These days, the sailing program offers summer classes to beginners, intermediates and racers between ages 8 and 16. Adult classes are held in the evening.

The sailing program celebration dovetailed with the town’s annual Harbor Festival and was highlighted by the premiere showing of a documentary about the program, created by Swampscott High School students who are planning a sequel.

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