About Weston Sailing

Racing Tradition. Rising Talent.

Founded in 2022, the Weston Sailing Team is a competitive and fast-growing program for students at Weston High School in Weston, Connecticut. The team welcomes sailors of all experience levels—from students new to the sport to some of the most accomplished junior sailors on Long Island Sound.

Our roster blends first-time sailors with experienced racers who train year-round at leading junior programs such as Pequot Yacht Club, Cedar Point Yacht Club, and other JSA-member clubs. This mix of backgrounds is a core strength of the program, fostsering mentorship, depth, and steady competitive development.

Home Base: Captain’s Cove
Spring Season: Practices begin in March, with the season concluding in late May or early June, depending on the racing calendar.
Practice Schedule: Three days per week, from 3:30–6:30 PM.
Transportation: Parents coordinate carpools for round-trip transportation, organized in collaboration with the team.

Tryouts

We can field only a limited number of boats each season. The good news is that there is always room for new sailors, and no prior experience is required. We encourage any student with an interest in sailing to participate in tryouts and join the team.

The Boats & the Racing

Weston competes in Club 420s, two-person dinghies sailed with a mainsail and jib. Teams consist of a skipper and crew, racing in team & fleet racing formats where consistency, teamwork, and tactical execution determine overall results.

Competition on Long Island Sound

Each spring, Weston sailors compete against some of the strongest high school programs in the region, including Staples High School, Fairfield Ludlowe, Brunswick School, Greens Farms Academy, Darien High School, and others.

Training out of Sail Black Rock in Bridgeport, the team commits to a demanding schedule of weekday practices, league regattas, and weekend events across Long Island Sound. Racing regularly occurs in varied wind and current conditions, preparing sailors for championship-level competition.

Championship Racing

The Weston Sailing Team competes within the Fairfield County Sailing League and is a proud member of the New England Schools Sailing Association (NESSA), the most competitive scholastic sailing district in the country and a regional division of the Interscholastic Sailing Association (ISSA).

The pinnacle of NESSA fleet racing is the O’Day Trophy, which serves as the NESSA Fleet Racing Championship. This district championship brings together top teams from across New England and is typically hosted at premier scholastic sailing venues throughout the region, including locations in Massachusetts and Connecticut.

Strong finishes at NESSA championships form the pathway to ISSA National Championships.

Sailing with the Best

At Weston Sailing, we’re part of a tradition that connects us with some of the most respected schools in the Northeast. NESSA brings together seven leagues and dozens of programs, including renowned institutions such as Choate Rosemary Hall, The Hotchkiss School, St. George’s School, Milton Academy, and Tabor Academy. These schools treat sailing as a core sport, with teams regularly competing at the national level.

Closer to home, the Fairfield County Sailing League stands among NESSA’s most competitive divisions. Its powerhouse programs include Brunswick School, Greenwich Academy, Greenwich Country Day, Greens Farms Academy, Staples High School, Darien High School, and Fairfield Ludlowe High School. Competing against this caliber of schools underscores how important sailing has become—not just as a sport, but as a mark of excellence shared by the region’s top programs.

What Defines Us

  • Excellence in competition — refining racing skills against the region’s strongest teams.

  • Depth of talent — a roster that blends beginners with championship-level juniors.

  • Commitment and grit — accountability, sportsmanship, and resilience at every practice and regatta.

  • Team identity — every sailor, from first-time crew to veteran skipper, contributes to Weston’s strength.

Our Mission

To develop confident, skilled, and competitive sailors who embody respect for the sea, loyalty to their team, and the drive to succeed at the highest levels of scholastic sailing.