Westport: A Sailor’s Haven

THE PICTURESQUE coastline of Westport has long been one of the town’s major attractions. For those who love the water, the town offers exceptional opportunities for sailing and boating. Westport is home to an outstanding sailing school and three yacht clubs, each with a proud history.

If you’re interested in experiencing sailing along our town’s coast, there’s plenty of opportunity to get out on the water at one of the following clubs.

LONGSHORE SAILING SCHOOL

This waterfront property, known as Longshore Club Park, was once the private estate of reclusive millionaire Frederick E. Lewis and may have inspired The Great Gatsby by former Westport resident F. Scott Fitzgerald. Today, Longshore includes a golf course, tennis courts, and a swimming pool. The Inn at Longshore and La Plage restaurant offer an unparalleled waterfront setting.

Founded in 1960, Longshore Sailing School is one of the oldest and largest community sailing programs in the country. The school operates seasonally, offering a wide range of classes (ages 8 through adult) for all types of sailors (beginner to advanced). Longshore also offers hourly boat rentals in the calm, protected waters at the mouth of the Saugatuck River. If you are new to sailing and want to try it out before considering membership at a yacht club, Longshore is the place.

CEDAR POINT YACHT CLUB

Cedar Point Yacht Club, known colloquially as CPYC, dates back to the Gilded Age. The club was founded in 1887, the same year that the Social Register—a directory of prominent families—was first published. Much like the Social Register, the original CPYC was very much a high society organization. The club’s annual yearbook includes a section titled “The Heritage of Cedar Point Yacht Club” which states that the club founders “were prominent, influential sportsmen” and “several were members of the New York Yacht Club.”

The club takes its name from Cedar Point, the point of land on the eastern shore of the entrance to the Saugatuck River. CPYC was the one of the first 40 yacht clubs established on the Eastern seaboard. In the early years of the club, CPYC was an association of sailors without a clubhouse. In the late 19th and early 20th centuries, most of the boats in the fleet were sloops and catboats.

In 1932, Cedar Point Yacht Club moved into a new building at the Compo Yacht Basin. The original building, known today as the Ned Dimes Marina Clubhouse, is now home to the Minuteman Yacht Club.

CPYC would remain at its Compo Beach location from 1932 to 1966, when the club relocated to its present location on Saugatuck Island. The property has a two-story clubhouse and offers stunning views and uncrowded conditions. Today the club has active racing fleets of Atlantics, Flying Scots, Lasers, Lightnings, Stars, Thistles, and Vanguards as well as cruising sailboats. CPYC has an active social calendar with events at the clubhouse and outdoor pavilion. The club has a charming private beach for members, offers stunning views of the Sound, and is well known for its breathtaking sunsets.

SAUGATUCK HARBOR YACHT CLUB

Founded in 1959, Saugatuck Harbor Yacht Club is located at the mouth of the Saugatuck River in Westport, Connecticut. The club has approximately 200 member families and 160 boats, each with its own slip. While neighbor Cedar Point Yacht Club is focused on sailing, Saugatuck Harbor Yacht Club has an even split between sailboats and power boats. Members are active with cruising, racing, and fishing, and the club offers a year-round entertainment schedule. Facilities at the club include a swimming pool.

In her 1996 article titled “Westport Wildlife” for The New Yorker, Barbara Probst Solomon put forth a theory that the novel The Great Gatsby was inspired by the summer of 1920, when newlyweds F. Scott and Zelda Fitzgerald lived in Westport. The Frederick E. Lewis mansion, known today as the Inn at Longshore, is theorized to be the model for Gatsby’s house. A large estate known as Great Marsh, owned by Henry C. Eno, was once located directly across the water and may have inspired Daisy’s house.

The main clubhouse for Saugatuck Harbor Yacht Club, a beautifully repurposed Queen Anne Style building, was originally the carriage barn and stable for the Eno estate. The building dates from 1887, the same year that Cedar Point Yacht Club was founded, and Eno was one of the founding members of CPYC.

Saugatuck Harbor Yacht Club enjoys reciprocity with Black Rock Yacht Club, Cedar Point Yacht Club, Pequot Yacht Club, and Indian Harbor Yacht Club, among others.

MINUTEMAN YACHT CLUB

In 1966, when Cedar Point Yacht Club moved to its current location at Bluff Point, the vacant clubhouse at Compo Basin became the home of a newly established club known as Minuteman Yacht Club. The building, known as the Ned Dimes Clubhouse, is owned by the Town of Westport. Minuteman Yacht Club events take place at the clubhouse and at Compo Beach.

Minuteman Yacht Club takes its name from the patriots who fought in the American Revolution. On April 25, 1777, 2,000 British troops under the direction of General William Tryon landed at Compo Beach. Patriots and Redcoats fought over two days of conflict at Danbury, Ridgefield, and Westport.

The Minute Man has become the most iconic symbol of Westport, honoring the heroism of patriots. On June 17, 1910, the Minute Man was commemorated in a monument given to the town by the Sons of the American Revolution. In 1935, the Minute Man became the emblem for the town centennial celebration. On May 6, 1957, the Minute Man statue made its national television debut on I Love Lucy. The Westport town flag, designed in 1986, also features the Minute Man.

In the mid-1960s, Bridgeport-based power company United Illuminating (UI) acquired Cockenoe Island, off the coast of Westport. After UI announced plans to construct a nuclear power plant, members of the Westport community—including boaters from Minuteman Yacht Club and Cedar Point Yacht Club—took part in grassroots activism to stop the projects. The town of Westport purchased the property and designated it as open space. In their Fourth of July issue for 1970, Life magazine called it “one of the most significant conservation victories in the nation.”

For many years, Minuteman Yacht Club was a club for boaters living in Westport. Today, Minuteman membership is open to non-residents, boat ownership is less common and dues are affordable. Minuteman is primarily a social club with an active calendar of events each season, from clambakes and cocktail parties to sunset soirées on Compo Beach. Each year, the club hosts a reception after the annual King Cup Race. The race is organized by Norwalk Yacht Club and the trophies are presented by Minuteman.

Minuteman Yacht Club is affiliated with Yachting Club of America, the national association of yacht clubs, and enjoys reciprocity with clubs listed in the Register of American Yacht Clubs.

Cedar Point, Saugatuck Harbor, and Minuteman are multigenerational clubs with families who have deep roots in the area. The clubs also welcome new members who share a love of boating and socializing on the water.

If you’d like to experience these clubs and the sailing school for yourself, this summer season is the perfect time to explore Westport’s waters.

By Matthew Longcore