Thimble Islands

Sea-ing the Sights

We’re on vacation! For the rest of the week, enjoy Daily Nutmeg editions past, starting with this seaworthy story from last August.

Branford’s Stony Creek section, situated on a picturesque shore along the Long Island Sound and home to beaches, residences and a few restaurants, is an understandably popular spot to visit during the warmer months.

Next time you’re in the neighborhood, though, think about heading away from the shore and towards the not-so-distant Thimble Islands.

Each of the Thimbles is small as far as islands go, yet some are much smaller than others. There are between 100 and 365 of them depending on how you define the word “island.” (If a rock poking above sea level counts, then there are 365.) While the collective name works descriptively—thimbles are pretty small, after all—the moniker actually derives from the “thimbleberry,” a hedge with bright red fruit that once grew plentifully there.

To explore the islands, you’ll need a motor boat, and every boat needs a captain. Perhaps it’ll be Captain Mike Infantino with Thimble Island Cruise, one of the groups that does regular tours of the islands. The company, owned by Infantinos since 1960, also provides private charter tours and seal watches.

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Captain Mike tells me that twenty-five of the granite islands are inhabited, with 95 homes total. The roughly 100 families who summer there make up the thimble-sized community of islanders who call this rocky archipelago home-away-from-home.

While the Thimbles may serve as a summer playground these days, they long stood stark and untouched. During his 45-minute cruises, Captain Mike tells boatfuls of curious visitors that the islands were formed over 18,000 years ago when the Late Wisconsin Glacier receded, leaving them in its wake.

Settlers didn’t catch on to their existence until Dutch explorer Adriaen Block discovered them during an expedition in 1614, when he also laid eyes on what would become New Haven. Other stories associated with the islands seem less like history and more like mythology.

It’s been said that Captain William Kidd, a seventeenth-century Scottish sailor and notorious pirate, visited the islands and buried treasure on one of them, though it’s never been found. In a no less romantic tale, Mother-in-Law Island reportedly got its name when a mother meddled in her daughter and son-in-law’s private lives. In angsty revenge, the two paddled away by the only boats docked there, leaving her stranded.

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One of the favorite stories among tour-goers, according to Captain Mike, is that of circus performer General Tom Thumb, who visited Cut-in-Two Island in the 1860s for a tryst with his love, “Miss Emily,” the daughter of an island owner. In a sad plot twist, the renowned P.T. Barnum, the General’s boss at the circus, wouldn’t let Thumb out from under his thumb enough for a marriage to proceed.

Those narratives may stretch credulity, but it’s a fact that President (and later Chief Justice of the Supreme Court) William H. Taft spent summers on David Island during two years of his presidency. Likewise that television personality Jane Pauley and her husband, Doonesbury author Garry Trudeau, own a home on Governor’s Island.

The islands and their accompanying structures are as diverse as their names. Money Island, with over 30 residences, is the most populated; of the other inhabited islands, many have only one or two homes. Should you take a tour, you’ll spot a few shockingly luxurious vacation homes, complete with pools, tennis courts and ornate architecture, while some of the spots are definitely more “cottage” than “villa.”

Captain Mike says he can go on and on about the islands he now knows so well—mentioning the hotels that once graced certain islands during the Victorian era, perhaps, or highlighting the seventeen-acre Horse Island, the largest of all, which is owned by Yale and utilized by the Peabody Museum for ecological research.

He packs as much information as possible into cruises, which depart six days a week, taking a break on Tuesdays, through the end of August. In September, operating days are reduced to Fridays, Saturdays and Sundays. In October, just Saturdays and Sundays through the 13th.

In other words, there’s more time this year to explore, but not a lot more. Climb aboard the next departing boat, and listen to the tales.

Thimble Islands Cruise
30 Indian Point Rd, Branford (map)
For tour schedule, click here. Each regular tour lasts approximately 45 minutes.
(203) 488-8905

Written by Cara McDonough. Photo #2 by Cara McDonough; others by Dan Mims.

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