The Thimble Islands are a group of islands located off the shores of Branford, Connecticut with the exact number of islands ranging anywhere from 25 to 365 (depending on who you ask and what they define as an “island”). Many of these wooded islands are topped with beautiful summer cottages built during the Victorian Era, and range from small summer cottages, to mini-mansions. Local legend states that the islands were named for thimbleberries, a relative to the black raspberry, but are seldom found in the area. Dutch explorer, Adrian Block was the first European to discover the islands in 1614, although multiple reports claim the Mattabeseck Indians knew them well and referred to them as Kuttomquosh, “the beautiful sea rocks.”

Kidd’s Island is named after the famous pirate captain William Kidd, who according to local lore buried treasure on one or multiple islands. In 1846, local resident William Bryan built the Thimble Island Hotel on Pot Island, one of the larger islands in the Thimbles. Bryan attracted tourists and treasure hunters alike by taking advantage of the legend that Captain Kidd buried his treasure on one or multiple islands. Also in summer of 1846 a steamboat excursion from New Haven to the Thimbles started, making the islands more accessible to the local population. This event along with others started a trend which continued to make the Thimble Islands a sought after travel destination, both for local Connecticut residents as well as those visiting from larger cities.