Orr’s Bailey Yacht Club
Orr’s Island, Maine USA

The Little Yacht Club That Could—And Still Can

The Orrs-Bailey Yacht Club is successful because it is small, and it’s small because that’s the way the families that make up its membership want it to be.


On the porch or around the waterfront, members of today’s smaller, less financially exclusive yacht clubs appreciate the emphasis on community.

A LINE OF ROCKING CHAIRS overlooks the long dock at the Orrs-Bailey Yacht Club clubhouse, a charming single-story cottage-style building with a wraparound porch situated on the southwest shore of Orrs Island in Casco Bay. The wooden chairs seem to beckon: an invitation to sit and watch children picking up shells on the shore, sailboats tacking out in the sound, or simply to rock and think. Yet at the Orrs-Bailey Yacht Club, or OBYC, these chairs have a more communal purpose. Friends, old and new, sit together; they look out across Merriconeag Sound toward the rolling green peninsula of Harpswell, and share memories of past summers on the water and their love of boating.

Yacht clubs were originally established as places for members and their guests to race together for prize money and to socialize. One of the earliest and most prestigious is the New York Yacht Club, founded in 1844, the first winner and long-time defender of the America’s Cup. As more clubs were established, the cost and exclusivity of membership posed a barrier to many would-be members. Disposable income was key not only to boat ownership but also to club initiation and membership fees. Today, smaller, less financially exclusive yacht clubs are thriving; their emphasis is on fun and community rather than services and social standing.

Most small yacht clubs are simple, lacking sit-down restaurants, full bars, tennis courts, and yacht maintenance services. Boaters and boating families flock to them, drawn by moderate membership fees, camaraderie, and a safe and healthy place for their children to learn to sail and build social skills. Today, the Orrs-Bailey Yacht Club is typical of the type. Its 235 or so members strive to preserve the simplicity and community values rarely found in larger clubs and sailing organizations. It has the reputation of being a place with a “great big heart,” where families come together on long summer evenings to sing together, talk, and play games after brisk and full days in boats out on the water.

Several generations have learned to sail during the 54-year history of the Orrs-Bailey Yacht Club.

OBYC Commodore Sue Baker is the second woman to serve as commodore in the club’s 54-year history. A woman with fond childhood memories of interclub races and lobster bakes, she recently took the time to give me a tour of the club’s new facility, built in the spring of 2007, and tell me where the “heart” of this small yacht club was born.

Commodore Baker moved aside a large stuffed swordfish from a table as we sat down in the conference room of the club. She told me that the fish was a remnant from the club when it was established in 1949 as the Sportsman’s Club, which sponsored fishing tournaments and boat races. In 1954 a few members branched off to create a group dedicated exclusively to boating, and the OBYC was born.

The old clubhouse was originally the recreation hall of an old turn-of-the-century summer camp. After years of patchwork maintenance, the club decided to build a new home. The new clubhouse, with exposed roof trusses and an aroma of fresh paint, has a conference room for the sailing school and meetings, a large kitchen, and an open foyer with doors to the restrooms. Every member of the club has a key to the facility; the foyer area is open at all times for boaters and visitors throughout the summer.

The OBYC clubhouse sits on the shore of Merriconeag Sound. “Merriconeag” is an Abenaki word meaning “quick carrying place.” It describes the narrow waters between the Harpswell peninsula and Orrs and Bailey islands, a distance of about one nautical mile. For a sailor today, the definition could mean “quick tacking place,” as it lends itself well to sail training.

The OBYC’s Abbot Fletcher Sailing School, named for notable sailor and Orrs Island resident Abbot Fletcher (see sidebar on page 82), offers seven one-week sessions for children age 8 to adults. (Youth involvement is significant: there are 52 in the club under the age of 18.) Originally, students sailed Ensigns and Turnabouts, but now they train in a fleet of eight Optimist prams and four larger Hunter 420s. The small Optis allow students to learn the basics of tacking, gybing, and steering on all points of sail.

“We really want kids to come from here well rounded,” said Commodore Baker.

The current goal of the sailing school is to establish an Opti racing team to re-establish the Maine Interclub Regatta—a two-day event—that in the past was hosted by OBYC. They hope to race against other small area clubs, such as the Harraseeket Yacht Club, the Merriconeag Yacht Association, and the Centerboard Yacht Club in South Portland.

“The enthusiasm among the sailing school committee is phenomenal,” said Commodore Baker. “It is the club’s largest committee, with 18 or 20 members, and it keeps growing.”

When I asked Commodore Baker what she considered to be unique about the Orrs-Bailey Yacht Club relative to larger clubs, she didn’t speak about the club’s services or the harbor; rather, she talked about the members.

“Socially [on an island],” she said, “the club was it for us growing up. Today these friendships still exist. Every season conversations start right where they left off.”

A new season at the club jumpstarts members into work mode to get ready for the summer. Members put in the floats and maintain the building and property.

“Most of the work around here is done by volunteers,” Commodore Baker said, pointing to a group of men outside setting up a kayak rack. “People get offended when they aren’t called to help out.”

In the foreground, Orrs-Bailey Yacht Club Commodore Sue Baker; in the background, the new clubhouse.

“When you are cleaning windows alongside someone,” said longtime member Judy Fletcher Woodbury, “you get to know them. That aspect means it isn’t just racing and socializing, it’s the team effort.”

If member enthusiasm accounts for a significant part of the success of the Orrs-Bailey Yacht Club, so, too, does the emphasis on multi-generational family involvement. The social and activities calendar reads like a menu for a five-star restaurant, with something for everyone of all ages and tastes, from first aid and CPR courses and Wednesday bingo night to the annual lobster bake—prepared in a pit and including clams, corn, potatoes, eggs, onions, and ice cream sundaes for dessert.

New members are treated as family at the club.

“We really try to welcome new members,” Commodore Baker said. “Two people sponsor a new member, and we welcome them at a special evening in June.”

New members and old alike are provided with lots of information to succeed. The club has a newsletter and a website, and members can register for programs via e-mail.

Members who once sailed as children in the club’s summer programs now return with children of their own, a homecoming that’s key to the club’s longevity. While longstanding members like Baker and Woodbury have deep childhood memories, the 52 children who are now part of the club through their parents’ memberships are the members of the future. As they one day in the future sit in the rocking chairs on the back porch, they will no doubt recount stories of sailing with their parents and grandparents.

With a new clubhouse, moderate membership rates, and a long list of events, the Orrs-Bailey Yacht Club is an enticing place for sailors to congregate. The heart of it lies in the simplicity of island life and the strength of community. Members anticipate that this special club will be going strong for at least another 54 years.

Susan Viets is a freelance writer. She lives in western Maine.

For more information: Orrs-Bailey Yacht Club, P.O. Box 236, Orrs Island, Maine 04066. www.obyc.org.

All in the Family

FIVE GENERATIONS OF THE FLETCHER FAMILY have called Orrs Island in Casco Bay home. The Orrs-Bailey Yacht Club has honored one of the most notable, the late Abbot Fletcher, by naming their sailing school after him.

OBYC provides a safe and healthy place for children to learn to sail and build social skills.

An engineer for 40 years at Bath Iron Works, Abbot raced and sailed along the Maine coast and beyond with his three children aboard the sloop Juanona, a classic Lawley sloop that was stripped to the basics—no engine or superfluous equipment. The trophies scattered about his daughter’s home attest to the races the Fletchers entered and won: Portland to Monhegan, and Marion, Massachusetts, to Bermuda, among others. Along with several years of cruising the Arctic Ocean in retirement, these racing victories and Abbot Fletcher’s desire to pass a love of sailing down to the next generation have created a powerful legacy that will be carried by the sailing school and Fletcher’s own family.

Abbott Fletcher’s daughter, Judy Fletcher Woodbury, recalls summers as a teenager aboard Juanona and later Majek, the Fletchers’ Tripp Javelin built in Marblehead, Massachusetts.

“Basically our vacations were sailing or racing on Majek,” Woodbury said. “My brother Max and I would deliver the boat and Dad would join us at the race.”

This was in the 1960s, when few women were interested in sailing. For many families an interest in sailing would often separate members. “I knew a lot of families who felt split by it because the women didn’t sail,” Woodbury said. “Now there are lots of women and girls sailing.”

Woodbury’s keenest memories are of bonding with her brother Max, her younger sister Kristin, and her parents on board Majek. “We would anchor at Isle au Haut,” she said, “and swim and even swamp the dinghy. Our parents let us do these things.”

The teamwork necessary on board during races brought Woodbury and her brother especially close. “Max and I sailed together so much,” she said, “we could communicate well. We each knew what the other was doing and we relied on each other heavily.”

This enviable closeness is a unique byproduct of families that sail together. There is a need for clear communication and joint effort that carries over into other areas of family life.

The Fletchers’ sailing heritage is firmly rooted on Orrs Island, where Abbot Fletcher’s grandfather purchased a home in 1924. With memories and relationships that run deep, the family continues to sail, race, and teach on the island, sharing their own exceptional love of boats. The skills and flexibility necessary to sail well as a family continue to be carried down through the generations. Abbot Fletcher has a sailing legacy that will endure: children and grandchildren with a simple love of boats and a sense of place on Orrs Island. —SV

Reprinted with permission of Maine Boats, Homes & Harbors
DIGITAL edition @ www.maineboats.com