Thimble Islands

The Thimbles are the exposed tops of a body of hard granite, rounded and polished by the glaciers that scraped across New England and left this coast studded with stone. The rock's warm pink-and-gray color, flecked with feldspar, is the signature of Stony Creek granite, prized by builders for both its strength and its glow.

Quarrying boomed here in the 1800s and into the 1900s, and Stony Creek stone was barged out to construct piers of the Brooklyn Bridge approaches, the base of the Statue of Liberty, and monuments and buildings from Boston to Washington. The old quarry scars and cut faces are still visible on some of the islands and along the nearby mainland shore.

How many Thimbles there are depends entirely on how you count. At high tide many rocks vanish, and estimates run from a couple of dozen habitable islands to more than a hundred named rocks and ledges, which is part of the fun of the place.

No New England archipelago would be complete without a pirate story, and the Thimbles have theirs. Local tradition holds that Captain William Kidd sheltered among the islands and buried treasure on one of them before his capture around 1699, and one island still carries the name Kidd's Island. No hoard has ever turned up, but the tale has drawn dreamers for three centuries.

The best-documented celebrity connection is to General Tom Thumb, the diminutive performer made famous by the Bridgeport showman P. T. Barnum. In the 1800s he summered on one of the Thimbles, and the island still bears his name. Over the years the islands have hosted an eccentric cast of artists, writers, and summer families drawn to their end-of-the-world privacy.

Long before any of that, these waters and shores were fished and gathered by the Native peoples of the Quinnipiac and neighboring communities, whose presence along this coast reaches back thousands of years.

Because almost every island is privately owned, the Thimbles are a place you experience from the water. Narrated tour boats depart from the Stony Creek dock through the warmer months, weaving among the islands while a captain points out the notable houses, the quarry sites, and the legends attached to each.

Sea kayakers also paddle the maze on calm days, and the wider Sound around the islands draws boaters, anglers, and seals hauled out on the rocks in colder months. Whatever the vessel, the appeal is the same: gliding through a village of islands where the streets are open water.

The mainland launch point, Stony Creek, is a destination in its own right, a compact waterfront village of clapboard houses, a small dock, and the summer Stony Creek Puppet House theater, easy to fold into a day at the shore.

Summer is the heart of the Thimbles season, when the narrated tour boats run their fullest schedules and the islands are alive with summer residents. It is also the busiest time in tiny Stony Creek, where parking is scarce, so an early arrival pays off.

Late spring and early fall are quieter and often clearer, with comfortable paddling on calm days and the first or last of the boat tours. In the colder months the tours wind down and the islands empty, but the shoreline stays scenic and seals sometimes haul out on the rocks, a reminder that the archipelago has a life well beyond the summer crowds.

The closest Boutel™ stays, so you can turn this stop into an overnight. Each is an independently owned, editorially selected place to stay.