Branford’s Stony Creek section, along a picturesque shore home to beaches, residences and a few restaurants, is a 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.
Numbering between 100 and 365 depending on how you define the word “island”—if a rock poking above sea level counts, there are 365—the Thimbles are indeed thimble-sized as far as islands go. But the name actually derives from thimbleberry, a hedge with bright red fruit that once grew plentifully there, and many individual islands have been given their own names.
To get a closer look, you’ll need a boat, and every boat needs a captain. Perhaps it’ll be Captain Mike Infantino with Thimble Islands Cruise. The company, owned by generations of Infantinos since 1960, provides narration, happy hour and sunset tours of the islands, along with Stony Creek Brewery cruises and private charters.
Captain Mike tells me that 25 of the granite islands are inhabited, with 95 homes total owned by families who may summer there, and he 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. 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 17th-century Scottish sailor and notorious pirate, visited the islands and buried treasure on one of them, though it’s never been found. In an equally romantic tale, Mother-in-Law Island reportedly got its name when a meddlesome mother intruded on her newlywed daughter’s honeymoon there. In revenge, the two paddled away by the only boats docked there, leaving the groom’s new mother-in-law stranded.
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, owned a home on Governor’s Island until 2017.
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 knows so well, mentioning the hotels that once graced certain islands during the Victorian era 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.
Infantino 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, cruises happen only on Saturdays and Sundays through the 15th.
In other words, there’s plenty more time this year to explore. Climb aboard, see the sights and listen to the tales.
Thimble Islands Cruise
30 Indian Point Rd, Branford (map)
(203) 488-8905
Website | Tour Info & Schedule
Written by Cara McDonough. Image 2 photographed by Cara McDonough; others by Dan Mims. This updated story was originally published on August 20, 2013.
