Tag Archives: Westport recreation

One More Golden Anniversary

Quick:  Name 4 Westport institutions that turn 50 this year.

Everyone knows Mitchells, Staples soccer and Staples Players.

If you didn’t think “Longshore Sailing School” too, join the club.  The lesson-and-rental place — located just beyond the pool, at the gorgeous juncture of the Saugatuck River and Long Island Sound — is one of Westport’s most overlooked treasures.

Longshore Sailing School

For its 1st 15 years, the sailing school was a Parks and Rec program.  In the mid-’70s, budget woes almost sunk it.  But former employee John Kantor rode to the rescue.   He made it a private enterprise.  It quickly caught a strong tailwind.

The building now houses a year-round office with 3 full-time employees.  There are 4 covered classrooms, a “great room” filled with photos, and a special weather station.

blog - Longshore sailing 2Longshore Sailing School offers 4 basic classes, from beginner to advanced.  That formula works.  But Kantor and his staff constantly tweak other offerings.  Kayaking is now huge.

While most students are youngsters, adults take weekend classes.  Two-thirds of them never sailed, but always wanted to.  The rest seek a refresher.

Despite its success, Longshore Sailing School faces the same choppy economic waters as the rest of Westport.  Parents are waiting a while to enroll their kids in summer classes.

Operations manager Donny O’Day — a 24-year-old in his 13th year with the school, as a student and employee — is confident that both sign-ups and daily rentals will surge.  “A lot of people who went to Martha’s Vineyard won’t be there this year,” he notes.  “Longshore Sailing is something they’ll definitely enjoy doing.”

In its 50th year, the school is trying new tacks.  On Saturday they partnered with the Westport Historical Society on a kayak/canoe trip up the Saugatuck.

An early June “throwback weekend” will feature original rental prices (and what O’Day calls “hideous navy and peach striped shirts”).

Longshore Sailing School is important to the town — and to its staff.  “It’s the summer job you never forget,” O’Day says.  “We had so many old employees at our 45th anniversary, we may limit the next one to managers only.”

And, he says proudly, all 9 new staff members this year are former students.

Happy 50th, Longshore Sailing School.  May the wind be at your back for 50 more.

Longshore Sailing School