Chatham Yacht Club Celebrates 100 Years On Pleasant Bay

By: Elizabeth Van Wye

July 4, 1921, the first Baybird race was held at what would become the Chatham Yacht Club. COURTESY PHOTO

Unless you know it is there, you might never know that the Chatham Yacht Club is off Fox Hill Road in Chatham Port. Situated on a half-acre of land along Pleasant Bay leased from the Eastward Ho! Country Club, CYC sits on the eastern shore of the bay, just beyond Jackknife Cove, and is marking its 100th year of promoting sailing and developing sailors with a series of historic sailboat races.

The yacht club was founded by "nautically minded members of the Chatham Country Club, the forerunner of Eastward Ho!" according to Ted Dickson, a historian and longtime club member. In 1921 the club established a regatta committee and ordered a fleet of 19 Baybirds, described as "18-foot gaff-rigged sloops with a centerboard and jib."  A sailing race to commemorate their arrival was held that summer, the first of many.

Seven years later, the regatta committee was dissolved and two independent yacht clubs were formed.  Chatham Yacht Club was located on Pleasant Bay and the Stage Harbor Yacht Club settled on the south side. 

Although promoting sailboat racing on Pleasant Bay was an early mission of CYC, by the mid-1950s, with the establishment of a sailing school, the education of future sailors became key as well.

After operating on a volunteer basis for a number of years, CYC decided to hire a sailing master in the '60s to oversee the operation of the club and it grew as a result.  Today there are 85 sailors in the youth program and nearly two dozen adults taking courses as well.

On the weekend of July 31, CYC will host the New England Beetle Cat Boat Association for the group's annual championship race.  The event, dubbed the CYC Centennial Regatta, will celebrate not only the club's 100 years but also the 100th birthday of the Beetle Cat, named after its developer, John Beetle.

The Chatham Regatta will be held on the first weekend in August. Dickson called it the "oldest and longest-running free regatta on Cape Cod, if not in the country." About 120 boats, from around New England and beyond, are expected to participate in the event.

The annual Baybirds race for the President's Cup is part of the Chatham Regatta.  Replicating that first race held in 1921, this special race will be run for the 100th year and Dickson believes it will be one of the only times a race has been held "with the same class of boats, for the same trophy, on the same waters, for 100 years."  In fact, one of the original boats that participated in the summer of 1921, a 20th Baybird that arrived late that year, has been lovingly refurbished and will participate in the race, along with a dozen or more other Baybirds.

According to Dickson, the best vantage points to view these races are from Jackknife Harbor and from the Pleasant Bay Community Boating campus. There are multiple races within each event and each are generally about 60 minutes long, although that depends on wind strength, he added.

There are currently 150 families who belong to the club, according to John Maggioni, commodore of the CYC.  Children as young as 7 or 8 can start with an instructor in a Beetle Cat, the classic wooden 12-foot gaff-rigged catboat. As they get older, students progress to a single-handed sailing dinghy called an Opti and then ultimately to one of the club's daysailers. By the time young sailors are in their teens they are often serving as instructors for the beginning students.  

In addition to boating skills, learning to sail brings with it many life lessons, Maggioni said.  Resourcefulness is key, and "being able to adapt," he added.

"Boats throw all kinds of challenges and we learn as we move from one boat to another," Dickson agreed, citing independence and responsibility as qualities learned. "We learn an appreciation for nature and the water when we are sailing at a high level. It's all about teamwork."

It's also about the community, Maggioni added. 

"Day to day the kids are developing community here," he said. "There is a relationship of trust and extended family that we are safe to go out, even when the winds are gusting."

Looking ahead to the next 100 years, Maggioni stressed the importance of dealing with environmental issues, including erosion of the beachfront.  A committee has been formed to look at long-term solutions, he said. 

"We'd like to make sure that future members have the same access to the bay that we've enjoyed so long."

For more information on the club, visit