Thimble Islands

The Thimble Islands comprise roughly 365 rocky islands and outcroppings scattered across Long Island Sound, forming a fragmented landscape of shallow waterways and stone formations. About 23 of these islands are inhabited, supporting roughly 81 homes that cling to the rocky terrain.

Dutch navigator Adrian Block documented and charted the islands in 1614, making them among the earliest recorded features in European maps of the region. The Mattabeseck Indians, the original inhabitants, named them Kuttomquosh in reference to the rocky terrain.

Island residents have built a close-knit community centered on self-sufficiency and independence from the mainland. Locals maintain strong traditions of boat-based living and neighborly connection despite physical separation.

Ferry service operates mainly in summer months, departing from Stony Creek harbor to transport visitors to select islands in the archipelago. Navigation through shallow waters and changing tides means schedules may shift, so planning ahead with local ferry information is important for a smooth visit.

President William Taft used Davis Island as his summer retreat, a fact many visitors overlook when exploring the islands. This presidential connection adds a layer of national history to what many see as a simple residential community.