While the annual boat parade on Cobbett's Pond has survived changing times over the past several decades, one related tradition has not. The inaugural Cobbett's Pond beauty contest was held in 1958, and quickly became a popular event in the community. Miss Cobbett's Pond was chosen by a panel of judges at a dinner and beauty contest held at Town Hall. Prior to the dinner, all of the contestants participated in a parade where their family, friends, and fellow Cobbett's Pond residents had their first chance to catch a glimpse of all the candidates before the title of Miss Cobbett's Pond was bestowed upon a single young woman a few days later. While the contest was only open to residents and campers of Cobbett's Pond, the committee included residents from surrounding towns; during the 1960 contest the head of the committee in charge of soliciting entries was a resident of Nashua. A committee comprised of local teenagers was tasked with canvassing the cottages and homes along Cobbett's Pond and registering girls between the ages of 12 and 18 as candidates in the annual contest. One lucky entrant, after being crowned Miss Cobbett's Pond, had the honor of being escorted around the pond during the annual boat parade, usually held a couple weeks later. Wearing a crown and riding on a small, decorated motorboat, the first Miss Cobbett's Pond, Marie Chadwick, is shown in the photograph above, taken during the 1958 boat parade.
Derek Saffie is an avid Windham historian who enjoys researching and sharing his collection with all those interested in the history of the New England town.