Engagement on Pleasant Bay

by Ted Dickson
I have been reflecting on Mike Fortenbaugh’s article for Scuttlebutt in July, and I offer “formulas for success” that we see with small-boat sailing on Pleasant Bay, a protected body of water on Cape Cod in Massachusetts that’s blessed by good sea breezes and minimal waves, and shared by the towns of Chatham, Harwich, Brewster, and Orleans.

There are currently two sailing clubs on greater Pleasant Bay – Chatham Yacht Club and Pleasant Bay Community Boating.

CYC was founded in 1921, and members sail out of a small room-one clubhouse (plus a small office and kitchenette) on land leased from Eastward Ho! Country Club. CYC’s Sailing School consists of instruction every weekday in Beetle Cats, Optimists, Sunfish, and c420s. The club owns a fleet of c420s, but most of the other boats are privately owned and freely loaned to the sailing school.

On Monday afternoons, there are beginner-level adult classes held in Arey’s C-14 catboats. There are sailing school races immediately following the morning’s instruction on Wednesdays and Thursdays. After the sailing school race on Wednesdays, there are open Junior Races and a beginner C-14 race for Monday’s adult students.

The club sponsors regular club races on both Tuesday and Saturday afternoons in the sailing school classes, with the addition of C-14s on Saturdays. The club also sponsors occasional social events for adults and families to further build community.

On the opposite side of the bay, you’ll find PBCB, which was founded 20+ years ago by my brother, John Dickson, with the help of many people from the surrounding sailing communities. This has grown from sailing off a beach at the head of the bay to a facility on the Orleans side with several buildings, a small boathouse, and fleets of Flying Scots, Sandpiper catboats, Optimists, c420s, and Sunfish.

Anyone can take lessons or be approved to take one of the boats sailing for minimal cost. PBCB hosts adult races on Friday nights in Flying Scots and Sandpipers. PBCB offers adaptive sailing and boating off of their ADA-accessible dock. In addition to its sailing program, PBCB also offers educational programming on marine and environmental science, complete with a speaker series and a floating classroom.

There are a lot of overlapping members between these two clubs on Pleasant Bay, with some instructors teaching at both clubs and other shared members also serving on the board of the Friends of Pleasant Bay, a grassroots environmental non-profit with a 40-year history dedicated to preservation of the bay.

Here are two snapshots of recent sailing on Pleasant Bay:

Wednesday, July 30:
Chatham Yacht Club hosted the Southern Massachusetts Sailing Association Gill Cup on July 30-31. This is an all-girl, bring-your-own c420 regatta for sailors aged 13-18 that has been raced annually since 1994. I piloted the mark boat for the event, assisted by my wife, our middle child, and other helpers.

As we motored out to set the course on Wednesday morning, we could see 41 c420s getting ready to race the Gill, in addition to 17 sailing school boats from PBCB and 23 sailing school boats from CYC. Kids and adults were having fun and learning all over the Bay!

The CYC kids were enjoying their Costume Day followed by Sailing School and Junior Races, and the instructors were as cheerful as ever, even if a bit tired from running the Sailing School Karaoke event the night before.

Saturday, August 2–Sunday, August 3:
Chatham Yacht Club hosted its annual regatta, first raced in 1921. We claim that this is the oldest continuously sailed free regatta in the country. There is no cost to compete, and all the organization–from shore crew, to patrol, to race committee–is done by club volunteers.

The CYC regatta is an ideal first regatta for new racers as well as a competitive one for experienced sailors: There is usually wind without waves, and the racing days are shorter since the courses are just off the beach. This year, 147 boats were raced by sailors ranging in age from 6 to 80+.

We adopted a unique regatta format in 2020, with two rotating time slots on each day:

Saturday morning: c420s on the Outer Line; Optis on the Inner Line
Saturday afternoon: Sunfish & Lasers on the Outer Line; catboats on the Classic (Inner) Line
Sunday morning: Sunfish & Lasers on the Outer Line; catboats on the Classic (Inner) Line
Sunday afternoon: c420s on the Outer Line; Optis on the Inner Line

This format allows sailors the opportunity to get further involved with the regatta–for example, sailors may race in two different classes of boats, or race in one time slot and run or patrol the races in the other. My family both races on the Classic Line and runs the race committee for the c420s.

While 37 c420s raced on the Outer Line on Saturday morning (including a few boats that stayed after the Gill), 60 Optis raced closer to shore on the Inner Line. The sailors came from all over the Cape and south shore. That afternoon, we had starts for three catboat classes on the Classic (Inner) Line: 12 fiberglass Arey’s Pond C-14s, 7 Sandpipers (from the PBCB fleet), and 10 wooden Beetle Cats (which I raced in with my wife). Simultaneously, we had 25 Sunfish, 2 Lasers, and 4 Baybirds on the Outer Line.

Baybirds (gaff-rigged main and small jib) were the original fleet raced at Chatham Yacht Club back in 1921 and were later adopted by the sailing camps on Pleasant Bay. Most of the Baybirds that are still racing are from the camp fleets and are mostly sailed by former Pleasant Bay Camp sailors.

The c420 fleet included racing coaches, collegiate sailors from Tufts, Boston College, etc., former collegiate sailors, as well as beginner c420 sailors. Sailors in the Sunfish ranged in age from 8 to 78. The Beetle Cat class included former collegiate sailors, several parent/child teams, husband and wife teams, a sibling team, two teenagers from the CYC race team, and a number of boats that have done very well in the New England Beetle Cat Championship Regattas.

On Sunday, we start earlier in the morning so that we can have awards ready by 3:00 pm. The awards are a celebration of racing featuring trophies that are prints of an original watercolor of sailing at CYC–a different painting every year by long-time member David Spring and donated by the Spring family since at least 2003.

We also award a Sportsmanship Trophy to each of the four racing lines, each named for a different family at CYC in honor of a family member that was lost to our community and is dearly missed: Annie Benson, Tina Spring, Lee Sheldrick, and Polly Dickson. The close community at Chatham Yacht Club remains one of its greatest strengths.

Many of the sailors in our community are multi-generational from families who have been sailing on the Bay for decades. Several are third- and fourth-generation descendants of the founding families of CYC, who were exposed to a love of sailing and of the bay from a young age.

They first learn to sail by racing with family members and then they begin sailing school at age 6, where they are taught by teenage and college-age instructors from club families.

During club races on Tuesday and Saturday afternoons, we have three very competitive family teams who are 50+ in age that race in the c420 fleet against collegiate sailors, race team members, and beginner racers.

Within this community, there is an egalitarian love for the sport that extends to being on equal footing with each other regardless of age, gender, or title. We don’t use honorifics, instead referring to everyone by their first name, which helps promote this inclusivity.

CYC has modeled and promoted women of all ages as great sailors, instructors, and leaders since its inception. We likely had the first woman commodore in the US back in 1943, and a CYC member was the first woman to win an intercollegiate sailing race in 1941.

Two of the current flag officers are women, and four of the last five Sailing School directors have been young women (two came from multi-general membership, and two from families new to CYC). We have had several teams compete in the Adams Cup finals over the years, and last year, the Coleman sisters from CYC became the first all-women crew to win the Day Sailer North American Championship.

In addition to our focus on inclusivity and egalitarianism, our community has always striven to make the Bay more accessible by keeping membership and lesson costs low at CYC, promoting a positive, volunteer-based egalitarian atmosphere; recruiting new families, and even providing adult instruction to the parents (and grandparents) of kids in Sailing School.

Used boats are often purchased from other members or are donated to grow the club fleets. There are Optis that have been passed between three or four families as their kids age out, though the boat names and sail numbers remain the same.

Members of CYC continue to serve on the board at both Pleasant Bay Community Boating and Friends of the Bay or as instructors at PBCB, broadening access to the Bay and aiding conservation efforts including volunteering as water quality testers through the Pleasant Bay Alliance.

Despite the many challenges facing coastal clubs, from real estate prices to water access to parking, sailing continues to be successful on Pleasant Bay. I hope this inspires you to share what makes sailing successful at your club.

Ted Dickson is a former Commodore of Chatham Yacht Club.