“We are either related to or we know probably 90 percent of the people here,” laughs Chatham native Winnie Lear.  Winnie and husband Bob, full time residents of Chatham's Old Village, are about as deeply involved in the community as two people can be.

From the Chatham Conservation Foundation to the Chatham Historical Commission, the Eldredge Library board of trustees to the board of the Orpheum Theatre, from the Chatham Alliance for Preservation and Conservation to volunteering at the St. Christopher's Episcopal Church Gift and Consignment Shop and the Chatham Cultural Council, the Lears are working for the benefit of their local community and enjoying it. Winnie has been a member of the Old Village Association for seven years, the last two years as president. 

Winnie, a Chatham native, can trace her family history back 13 generations, “back to when the land was bought from the Indians.” She attended Chatham schools, and as much as it can be said that Chatham made her what she is today, her family also made Chatham what it is: her father, Charlie Shepard, owned a plumbing business, and as a child his father owned the plumbing business which worked on the construction of the Chatham Bars Inn in 1912. The couple still owns the original plumbing shop, now a private residence on Main Street in the Old Village. Winnie's mom taught English, history and Latin at the high school, and her grandfather, John Shepard, founded the Cape Cod Baseball League.

“I am sure I must often encounter people I knew back in high school, but they look a little different than they did at age 17 or 18, so I may not recognize them,” Winnie laughs.

Winnie grew up, as did her mother, in the Old Village in the Hallet Lane, School Street area. She and Bob lived in Philadelphia for 40 years, where they raised their three children. Winnie taught fifth grade, all subjects, at German Town Friends School in Philadelphia and in public schools.

Bob worked as an attorney for 40 years, focusing mostly on educational issues, mostly involving students and teachers with disabilities. He was legal council for the Philadelphia school district and also maintained a private practice.

“When I first retired eight years ago and we came here full time, I was asked to join the Chatham Conservation Commission, and I did for five and a half years,” Bob says. “I was appointed to the Chatham Committee for the Disabled for two years after I left the Conservation Commission, and I was also asked to be trustee of the Conservation Foundation, which is a better fit for me. I am also a trustee for the Eldredge Library and a new member of the Historical Commission.”

The Lears' four grandchildren, who reside in Acton and also in Philadelphia and Brooklyn, enjoy the same Old Village summertime fun that their family has for generations when they come to visit. Bob enjoys boating, as a member of the Monomoy yacht Club, as well as shellfishing, especially oystering, and fishing. Winnie says with a laugh that she neither digs nor eats clams, and she is not a big fan of swimming in the ocean these days, with the cold water temperatures and sharks.

“I grew up so close to the Mill Pond, and that was always such a safe place,” she recalls, “though we always had sharks here. When I was a little girl, a friend's family had a camp on Monomoy, and there were sharks.”

The Lears receive a lot of satisfaction from the many ways they are involved in the community. Through membership on the board of directors of the Chatham Orpheum Theatre, for example, Winnie says that they have expanded their horizons in unexpected ways.

“We've been on the board of the Orpheum from the beginning, and now I am the secretary, which means I am on the executive committee,” Winnie explains. “It has been very interesting. I've met a lot of people, including local filmmakers and artists. It was been so rewarding, providing opportunities like the Low Sensory Film Series and working with nursing homes. Our mission seemed ambitious, and it has been fulfilled. Its been a lot of work, but it has been good.”

The work that has been accomplished though the Old Village Association has also been a source of satisfaction.
“There have been some issues around demolitions and and changes to neighborhood,” Winnie says. “The Old Village is on the National Historic Register, so construction and demolition are important issues. We made Hallet lane one way, the only one-way street in the Old Village, and we also managed to create the only crosswalk in the Old Village, the Water Street steps, and the Water Street and Andrew Harding Lane signs.”

“We can use more crosswalks,” Bob adds.

“The Eldredge garage is another issue that we are concerned about,” Winnie says. “The seems to be some denial of a parking problem in Chatham, but it is a fact. Yet we are concerned about open spaces becoming lost if it becomes developed.”

It seems impossible to imagine, but the Lears somehow manage to have free time remaining in their days for other pursuits.
Bob is a member of Chatham Beach and Tennis, which his grandparents founded. Winnie loves to sew, knit, cook and entertain.

“I am not a gardener,” she says, “But I do love doing all of these things, as busy as I am with our time consuming adventures.”