Our Hamptons

Towd Point, Southampton and the Tupper Family Legacy


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Esperanza and Irwin have a special visit with Charlie Tupper. The Tupper's presence at Towd Point started in the early 1920's. Charlie's grandfather (Frank Edwin Tupper) bought the property on Davis Creek in about 1917 or 1918. The land reminded him of his native Nova Scotia. When he bought it, the property cost $7500. The house, initially called "Ramblers Cottage" for the rambling roses growing along side, was built in about 1907, along with several other large "cottages" along the bluff on Davis Creek overlooking Little Peconic Bay. The house had a large master bedroom on the first floor off the living room and seven bedrooms on the second floor. It was a summer home so it wasn't heated or insulated. There was a huge fireplace in the living room. Electrics were from a battery-system (no idea how they charged the batteries, probably with a gas-driven generator), there was a small "battery house" behind the barn that was about 200 feet behind the main house, there was also a small 2 bedroom quarters for "servant staff".  Some very early photos have the small servant house just behind the main house, but at some point it was moved back and attached to the barn and a 2 car garage with a small storage room was put behind the main house. The barn itself had 2 stables and an area to store a carriage or two and a large workbench, an upstairs with one finished off room and a big open area. Somewhere along the way (1930s or early 1940s), he built 3 cottages for rentals to the west of the main house on Davis Creek. Each cottage had a name. "Love in a Mist", then "Marshitern" and last "Flower House".  Love in a Mist and Flower house were prefabs with Flower House being a present he bought for my grandmother from the NY Flower Show.  Marshitern was a typical summer cottage assembled on cedar pilings right on Davis Creek.  The houses were typically rented, like all summer houses, Memorial Day to Labor Day ... I seem to recall they went for about $1500 a season. A lot of the renters were repeat renters. Love in a Mist was rented in the late 50s by Southampton Insurance man Maurice Cunningham, his office was on Main Street.  These 3 houses still exist and are extensively renovated and modernized. The main house was eventually called just "The Ramblers" but as kids, we called it "The Big House". Charlie regaled us with stories of growing up here, too numerous for this space. A not to be missed podcast. Special thanks to Artist and Friend Casey Chalem Anderson, whose series of paintings of Towd Point were a source of inspiration for this episode.

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