Chatham Yacht Club

Teaching Love of Sailing on Pleasant Bay Since 1921

Members of Chatham Yacht Club have been sailing Pleasant Bay since 1921!


With the introduction of Covid-19 Immunizations, our members were able to participate in a number of joyful celebrations.  These included:

Commodore's Cocktails 

July 4th Parade

Sailing School Picnic

Telesmanick Championship Regatta               & Celebration Dinner

Baybird Fleet Sail

Commodore's Buffet Centennial Gala

CYC Centennial Regatta

Last Hurrah!

See Below for Centennial Tidbits

Chatham Yacht Club was founded on three principles that remain central to the Club today:

  • To promote one-design sailboat racing on Pleasant Bay 
  • To teach sailing to young people 
  • To encourage active volunteerism in service to the Club

The Chatham Yacht Club (a.k.a. CYC) has been dedicated to the promotion of sailboat racing and the development of sailors since 1921. CYC provides sailing instruction to children, adolescents, and adults, and organizes racing experiences on Pleasant Bay.

Introduction: The Spirit of CYC: by Ted Dickson, Jeff Howell, et alia

The Chatham Yacht Club (a.k.a. CYC) has been dedicated to the promotion of sailboat racing and the development of sailors since 1921. CYC provides sailing instruction to children, adolescents, and adults, and organizes racing experiences in the Pleasant Bay area of Cape Cod, MA.

Chatham Yacht Club has always been more of a concept than a building. It is a community of people who work together to promote sailing and one-design racing on Pleasant Bay. One way that this community is unique is in the amazing hidden lives of its members. We see sailors and patrol boat operators and dock committee members and people doing maintenance projects. We do not always realize that we are also seeing accomplished doctors, teachers, professors and college presidents, accountants, ministers, social workers, engineers, business leaders, and even ambassadors.

Another more important way that this community is unique is how each generation trains and teaches the next generation through coaching, conversation, mentoring, and modeling, transferring values such as sportsmanship, seamanship, and voluntarism as well as sailing and teaching skills.

At CYC, young sailors compete against older champion sailors in many kinds of boats. In the 2020 regatta, two sailors in their fifties won the 420 class and the C-14 class, a 60+ year-old Sunfish sailor defeated the teen-agers, and in the Beetle Cat class, the teenager sailing with his father outsailed the older sailors. This older generation also mentors the sailing instructors who then pass on all of these values and skills to the next generation.

We love to sail and do not worry about frills. Our place has been on the water.

In 1921, some nautically minded members of the Chatham Country Club, the forerunner of Eastward Ho!, formed the Regatta Committee to promote sailing on Pleasant Bay. They commissioned from a Marblehead shipyard a fleet of 19 Baybirds; which were eighteen-foot gaff-rigged sloops with a centerboard and jib. A 20th boat arrived by train later that summer.

The first CYC race was on July 4, 1921, in the newly purchased Baybirds. The Regatta Committee flourished until 1927, when the Country Club decided that sailing and sailboat racing were not central to their activities. Members of the Regatta Committee continued to be committed to sailing, however, and went on to found two rival yacht clubs; one on Pleasant Bay, which became the Chatham Yacht Club, and the other on a bluff overlooking Stage Harbor, which was named, appropriately, the Stage Harbor Yacht Club.

For many years, the only property of the CYC was a dock jutting out into Pleasant Bay. CYC continued to promote racing on Pleasant Bay throughout the 1930s and 1940s. In the mid1950s, two enthusiastic teenage volunteers started a "Shore School" to teach sailing and racing to the children of members. Classes met on Thursday mornings, and children, as young as four, were taught in borrowed boats by an all-volunteer staff of teenagers. In 1955, Arthur Peterson and John T. Ryan negotiated with Eastward Ho! to rent land so that the Club could build a small clubhouse.

In the Sixties, the all-volunteer staff of the Shore School gave way to the Club’s first hired Sailing Master. Since then, the Sailing School staff has grown as enrollment increased. The sailing program expanded first to two mornings a week, then onto four mornings and three afternoons.

In 1975, CYC designated its oldest trophy, the President’s Cup, for the Saturday Day Sailer Series. This series became the premier racing event for CYC’s top sailors, some of whom also competed in Stage Harbor’s Sunday races. CYC helped host the 1979 and 1985 DSNACs on Pleasant Bay.

Through the years, CYC sailors have represented the club successfully in regional and national regattas. CYC teams have won the SMSA Cumming Cup (junior triplehanded), the SMSA Nash Cup (doublehanded), the SMSA Ginn Cup (men), and the SMSA Prosser Cup (women). Some of these teams have advanced to the nationals.

CYC sailors have also competed in New England Beetle Cat Association events, including winning several junior and senior competitions, and in Day Sailer Association regattas, including winning many regional and national championships.

CYC’s tax-exempt status is based on its promotion of local, regional, and national sailing competitions. It has hosted a number of championship regattas through the years. The ability to host these events depends on the volunteers at CYC who organize the regattas, run the races, provide safety patrol, house visiting sailors, and donate everything ranging from food to the trophies.

Each year on the first weekend of August, CYC hosts the oldest and longest-running free regatta on Cape Cod, if not in the country. Around 120 boats from Cape Cod as well as from around New England (and even further afield) participate each year.

CYC members are dedicated to continuing to pursue the club’s mission of promoting sailing and developing sailors of the future. We will continue to teach sailing and racing, to train outstanding racers, and to host local, regional, and national regattas. CYC members are also active in community-supporting activities such as high school sailing, Pleasant Bay Community Boating, Friends of Pleasant Bay, and the Marconi Center. 

CYC History:

Ted Dickson is working on completing his history of CYC. Part of the format is like a members' scrapbook. To fill this, he is still looking for more memories and photos. Some writing prompts to consider: How did you start sailing at CYC? What are your favorite memories from sailing at CYC as a child? What has been your most memorable race? or boat? or sailing partner? or sailing instructor? We want every CYC family to be included!

In addition, if you are a student who needs an independent project to work on - perhaps by conducting Zoom interviews - or anyone else who wants to help, contact Ted Dickson.

Centennial Tidbits Below

Beetle Cat Sailors:

CYC is hosting the New England Beetle Cat Boat Association’s annual Telesmanick championship regatta on Saturday, July 31 and Sunday August 1, 2021 (this is the 100th birthday of the Beetle Cat, so we are expecting a lot of boats!). Cathy Taylor, Roy Terwilliger and Ted Dickson are busy with the initial planning, but will be counting on lots of volunteer help next summer! We also hope to have as many as 20 CYC boats sailing in the regatta and 40 overall. If you are interested in sailing and do not have a boat, work on finding one! Or consider buying a new or used one and joining the CYC fleet. If you are interested in buying a used boat, contact Ted Dickson who may have some leads.

Centennial Reflections & Tidbits

Read this fantastic article in Yankee Magazine - A salute to Cape Cod’s unsinkable Beetle Cat.

Cape Cod’s Beetle Cat | Up Close

A fleet of Beetle Cats race to the finish at Chatham Yacht Club (Cape Cod Times)