About Weston Sailing

Racing Tradition. Rising Talent.

Founded in 2022, the Weston Sailing Team is a dynamic program for students at Weston High School in Weston, Connecticut. We welcome brand-new sailors while also developing some of the region’s most competitive talent. Our roster blends athletes with no prior sailing background alongside top junior sailors from Long Island Sound, many of whom train at Pequot Yacht Club, Cedar Point Yacht Club, and other leading JSA member clubs.

Competition on Long Island Sound

Each spring, Weston sailors line up against some of the strongest high school programs in the area, including Staples, Fairfield Ludlowe, Brunswick, Greens Farms Academy, and others. Training at Sail Black Rock in Bridgeport, the team commits to a demanding schedule of practices, league regattas, and weekend events across Long Island Sound.

A Pathway to the Next Level

The Weston Sailing Team is a proud member of the New England Schools Sailing Association (NESSA), the regional district of the Interscholastic Sailing Association (ISSA). These affiliations give our sailors the chance to advance beyond local competition into regional and national championships. Our program bridges junior sailing at the club level with the highest tiers of high school and collegiate racing.

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.