The Thimbles don’t discriminate: Any outcropping, even a vegetationally challenged mound submerged during high tide, can join the club. As for the definition of “inhabited”: Most of the owners occupy their “cottages” (another fanciful use of language) during the summer months. For many pages of the calendar, the islands are deserted.
Details: Thimble Islands, Conn.
But on a warm day with a thin comforter of clouds, winter seemed as far away as the North Fork of Long Island, a dark blur on the horizon. Dinghies carrying dogs and groceries zipped around the water. Children dared each other to jump off the dock into the unknown depths. Beachgoers stretched out on sandy Stony Creek Beach, on the mainland, their faces turned toward the islands, a drizzle of hard cookie dough clumps topped by architectural cherries.
All but two of the islands are private, so you can look but not touch down. The best vantage point is from a seafaring vessel, preferably one with an open top deck and a bar. From May through October, tour boats shove off from Stony Creek Town Dock and trace crazy-eights around the islands.
My family and I boarded the 44-foot Sea Mist, declining an offer from a man with a dangling earring and a bathtub-size boat. (A town worker said that the sightseeing trips follow the same route and the same script.) I carved out a corner on the second level, near a flapping pirate flag and a set of stairs a young crewmember scaled to take our beverage orders.
Capt. Mike Infantino, who controlled the wheel and the microphone, started the tour on the far left side of the timeline: 15,000 years ago, when the Late Wisconsin Glacier receded, leaving behind a giant marble-toss of pink granite and erratics (large, misshapen boulders). In 1614, Dutch explorer Adriaen Block, the Magellan of Long Island Sound, discovered the area, adding the Thimbles to his collection of discoveries.
The islands’ moniker doesn’t derive from the obvious — their sewing-button cuteness — but from the thimbleberry, which once sweetened the banks. The red berry is now rare; after a dedicated search, I finally found it at the Thimbleberry cafe in Stony Creek, but it was in jam form and imported from Michigan.
I’d heard that journalist Jane Pauley and cartoonist Garry Trudeau own a home on one of the islands, but Capt. Mike was not TMZ-ing on the islanders. To protect their privacy, he would not reveal the identities of the 100 families occupying the 95 homes. (One exception: Yale owns Horse Island and uses it as an ecological lab for its Peabody Museum of Natural History.) But he had no qualms about driving in close enough for us to see the tennis court, formal gardens (with well-manicured privets) and English Tudor-style mansion on Rogers Island, the serpent and dolphin statues on West Crib Island and the Malibu Barbie pool that juts 25 feet over the rocks of Davis Island. Nor did he refrain from pointing out the potted palms that the owner stores in a greenhouse on Rogers Island in the winter.