Chatham Yacht Club

Teaching Love of Sailing on Pleasant Bay Since 1921

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Honoring A Beetle Cat Legend, Mr. Roy Terwilliger

–Ted Dickson

Excerpt from the program for the Leo J. Telesmanick Champtionship Centennial Regatta held at Chatham Yacht Club 2021

Roy Terwilliger was born in East Hartford, CT and his days of “messing around in boats” began on Long Island Sound, where his family built a home in Milford, CT. It was there that Roy’s love of boats was born, and he learned to sail many different kinds of dinghy boats. Roy was forever hooked! After college, Roy married his Glastonbury, CT neighbor and sweetheart, Roxana, and subsequently started a family. They raised their three boys, Leighton, John, and Douglas primarily in the Annapolis, MD area. It was in Annapolis that Roy sailed wooden Snipes. During that period of time, Roy also completed the building of a Snipe that his father had begun many years earlier.

The Terwilligers were very involved in the Severn Sailing Association in Annapolis. Roy and Roxana also owned a 420, two Lasers, and an Optimist. Roy crewed on many much larger boats as well. He participated in several Annapolis to Newport Races, a Marblehead to Halifax Race, and was on the water every weekend June through October and at least one evening per week. According to Roxana, “Roy had a lot of friends that needed crew!”

Throughout his life, Roy has maintained his love of boats, the water, and sailing. In the 1980s, just before the Terwilligers moved to Cape Cod, wooden Beetle Cats caught Roy’s eye. It was the perfect boat to single hand (or so Roy thought), and you can imagine his surprise when he found out that he had to have a crew in order to race at Chatham Yacht Club! At one time, Roy owned three Beetle Cats, and an Opti too.

It was in college that Roy’s interest in classic cars came to be. As a matter of fact, Roxana had little idea of Roy’s passion for boats! Over the years, Roy and Roxana acquired an MGTC, a 1956 VW Bug, a Renault, a Jaguar 120, a bug-eyed Sprite, a Fiat, and a Porsche, all of which they still own today!

At Chatham Yacht Club, we have been the very fortunate beneficiaries of Roy’s intellect, enthusiasm, expertise, and love of sailing and racing sailboats. Roy has held the position as “Head of the Beetle Fleet” for nearly thirty years at Chatham Yacht Club. In that capacity, Roy has educated many sailors regarding the fine points of Beetle Cat boats, including rigging, racing techniques, and wind currents. He has given boat parts to many in emergency situations, and advised on repairs and best boat practices. In many cases, he has done repairs for owners himself, and has also restored boats to get them back on the water with the rest of the fleet.

He has lent his own Beetle Cats to the CYC sailing school for many years. He has matched up sellers to new Beetle Cat owners, not only allowing them access to the joys of owning these sweet, wooden boats, but also keeping these boats on Pleasant Bay. In his younger days, Roy would choose young crew members under the guise of educating them on the fine points of racing Beetle Cats, but those of us in the know understand that those choices were primarily made on weight alone! Whatever the reason, many of Roy’s young crew have turned out to become excellent sailors themselves as adults.

One such crew, Richie Dart, remembers: “Even though it was 20 years ago, I still remember when I was asked to crew for Roy; although I was young, I knew what an honor it was to be asked to crew for Roy. Roy not only taught me key sailing and racing fundamentals but what I took away from those years was Roy’s passion for being on the water. Without intentionally doing so, Roy showed me how to follow my passion no matter my age.”

Roy has helped to rig, launch, upright, bail, tow, repair, and restore Beetle Cats over his long tenure at CYC. Roy has represented Chatham Yacht Club on the NEBCBA board for many years as well, attending meetings in all seasons and distributing information as needed. Over the years, he has won nearly every award at Chatham Yacht Cub. He has been the “go to” Beetle Cat person in this region of Cape Cod for over thirty years. We salute Roy Terwilliger, husband, father, grandfather, and friend; for his enthusiasm, generosity, knowledge, and leadership in the world of Beetle Cat sailing and racing, and for his kindness, generosity and friendship both on and off the water!

Roy Terwilliger Involvement with CYC


Interview by Max Wesp, 2021

Q: How did you get involved with CYC?

Well, my parents bought this house on the Cape; and my kids started working here when they were in college. We would go down to Bay Road and watch the boats racing out there. And actually, my one son raced a Laser, but he never raced at CYC, he would race it over in Hyannis. Finally, when I moved up here, I think it was 1993, I decided to find out about joining. The ironic thing about it was, at the time I lived in Pittsburgh, and the person who answered my letter lived in Pittsburgh too, she was the membership chairman. So basically, I watched boats on Pleasant Bay when we moved here and joined shortly after that. Before that, I’d been a member of the Severn Sailing Association, in Annapolis, but I finally got into racing a Beetle Cat.

Q: What do you think is the purpose of CYC?

Well, I think the purpose of CYC is primarily education. It’s kind of interesting nowadays with PBCB because you know that has a similar approach, but much more general than CYC. While I still think the purpose of CYC is primarily the sailing school and education, I also think that it still provides an opportunity for racing, for people like myself, who are way beyond sailing school. 

Q: What are some of your favorite CYC memories?

Wow, so many, that’s hard to figure. Well, there is my first memory; and that is the first race that I sailed at CYC. The wind was blowing, and I didn’t know how to reef my Carl Dickson came over and stood in the water, and showed me how to reef my sail. Then we went out and started the race, and I led the race around the whole course, until the last leg when Carl got me in a tacking duel, and he passed me and went on to win that particular race, and I came in second. But that was my first introduction to racing at CYC. In fact, it was funny because when I started off, I didn’t really know the course and I wasn’t sure what I was doing, and here I was out in front; but I managed to get around okay.

Another memory I have was one time we had a single-handed race with Beetle Cats, with only one person in the boat. During that race, I can remember crossing tacks with John Dickson, who is probably one of the best sailors at the club, and I tacked underneath John, what they call a lee bow effect, and forced him to tack in the other direction. So, I went on to win that particular race, and again these are memories that are easy to remember because I won things.

Q: How do you think CYC will impact the next generation of sailors?

Well, I think it will be the same as it has all along: just giving people the opportunity to get on the water, learn how to sail, and race, although there is not one hundred percent interest in racing, not everybody who gets involved wants to race, they might just want to sail just not necessarily racing. I hope it affects people of the future the same way it always has...the opportunity to sail and enjoy sailboat sailing, as well as sailboat racing.

Q: How has CYC impacted you and your family?

Well, my family of course because I am a big sailor, and always have been. I guess the most impact is my son John, who lives here on the Cape, and he’s in his forties and fifties, but he crews for me on my Beetle Cat, on Saturday races. So, we get to be pretty close, and sail and race together, and enjoy that kind of thing. And of course, we lived in Annapolis, Maryland for a long time, and all three of my kids got into sailing while in Annapolis. Now, my oldest son, Leighton who lives in New Hampshire is still very active in sailing, in fact, he just bought a 30-foot sailboat up in Maine. My youngest one, who lives in Maryland, doesn’t sail much, but all three of my kids followed me and got involved with sailing a little bit. Now, my wife does not sail, she has never been a sailor because at first, she got seasick when she was sailing. So she never picked up the sailing, but I carried it on through my three kids. 

Q: Overall, why do you love CYC?

Well, I think what’s the most important thing is the people, they have a lot of nice people that are fun to be with. To me the best part about CYC is to walk down past the golf course, walk onto my boat, and immediately go out and go sailing. And you know, when I was a kid I used to sail by myself, in Milford, Connecticut on a Snipe, which is a fifteen and a half foot sailboat. I can remember, going out on my Snipe, by myself in Long Island Sound, and practicing handling the boat by myself, and I can remember standing by the mast, and remember this is not a Beetle Cat, this was a boat that had two sails, I would stand by the mast, and let the boat steer itself. I would lean windward, and it would head off, and lean-to leeward and it would head up, and I learned an awful lot just going out and sailing by myself. Well, that’s what I think is so great is you can just get down there, and meet people. A couple of years ago, we started teaching adults, you know we had sort of a sailing school group that taught adults, and I participated in teaching that, and we started to get more adults involved in racing because when people go beyond sailing school they aren’t sure what they want to do. As far as I’m concerned, CYC is just a great place to be with great people, and go down and go sailing.”

Chatham Yacht Club | P.O. Box 531 | North Chatham, MA 02650

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