During these dog days of summer, a trip to the Long Island Sound waterfront is a great place to stave off the heat. A refreshing swim and offshore breezes provide a welcome respite from oppressive summer temperatures. It seems fitting the next stop on our neighborhood series features the waterfront community of Shippan. Shippan’s history is as old as the history of Stamford, as it dates back to July of 1640. For the first fifty years, the beautiful peninsula served as corn fields. By the end of the 17th century, Shippan, like the rest of Stamford, was given to individual owners as determined by the Stamford proprietors in their town meetings. One of the most interesting land ownership stories is that of an investor named Michael McDeavitt who purchased the 1870 Ocean House, a hotel for summer tourists, which he renamed either “The Shippan House” or “The Shippan Point Hotel”, depending on what you read. The Shippan House was located on the site where Woodway Beach Club stands today. With the vision of expanding the amenities, by the end of the 1880’s McDeavitt had added a beach pavillion, bathing houses, a two story high casino and a carousel. The carousel was later moved to a new site (now home to the Marina Bay Condominium complex) and remained there until the 1970’s.
Another more recent favorite memory was the Star-Lite drive-in move theatre located on Shippan Ave across from Cummings Park. Stamford’s first & only drive-in was open for 20 years – 1951-1971 and gave many nights of enjoyment under the starry skies. 
From cornfields to casinos to carousels, Shippan has seen many transformations in its long history. Today, Shippan has about 1,200 homes spread across one square mile. Housing options vary from grand seaside estates, 1900’s vintage homes on quiet side streets to waterfront condominium complexes. With a half dozen clubs, marinas, and a range of beaches, Shippan also defies the car-dependent stereotype of other bedroom communities. According to residents, they will tell you that in warmer weather they walk almost everywhere.
Speaking of walking – it is common for residents to move from one home to another in the neighborhood. The practice has been called the “Shippan Shuffle.” It’s not unusual for people to have lived in more than one house in the neighborhood during their lifetime.
If you are socially inclined, there are many opportunities to meet your fellow neighbors. The Shippan Point Association is a membership-based organization which lists beautification and safety as among its missions. Members of the Gourmet Club take turns hosting potluck dinners, while the Shippan Garden Club famously hosts a yearly wreath-judging contest called the Doors of Shippan.
If your dream is to live by the Sound, walk to the beach, or spend your idle hours boating plus be part of an active community, take a look at the easy, breezy lifestyle of Shippan. It just might be the right fit for you!
Check out my new listing at 57 Downs Avenue in Shippan – it could be just the right fit!
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