Connecticut’s Thimble Islands

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Traveling along Route 95 just east of New Haven, Connecticut, my wife spied a small sign that said “Thimble Islands, Next Exit.” We have been up and down this road for decades and seen that sign many times before, but today we had no place to go and all day to get there, so we took the exit for Stoney Creek and meandered along until we ran out of road. A few minutes later, we were aboard a small cruise boat that would take us to see these Thimble Islands, whatever they were.

Our captain explained that a thimble is a geological curiosity also known as a drumlin. It’s a granite outcropping that juts up above the surface of Long Island Sound just off the coast of Connecticut near Branford. There are about 3 dozen of them. Some are several acres in size; some measure just a few hundred square feet.

As we motor along, we see several substantial homes that are all flying the same nautical signal flags out front. Our guide tells us those flags indicate they are all owned by the same family, though no one will tell us exactly who that family is. Once a week, a contingent of caretakers visits each one to cut the grass and change the linens – just in case an owner decides to stop by. We are told many of them have not been occupied in years, but they are kept in constant readiness nonetheless.

Local legend says that Captain Kidd used to visit the Thimble Islands and buried some of his ill gotten treasure hereabouts. Even though no booty has ever been found, the legend lives on. Our captain takes us to one obscure inlet where a small vessel could easily hide and not be seen by other boats passing by.

Back on shore, the compact Stoney Creek community has two restaurants, The Thimbleberry that overlooks Long Island Sound and Lenny’s. Both are inexpensive and feature local, home cooked meals in comfortable surroundings. Two local B&B’s cater to visitors who want to stay overnight, the Thimble Island B&B near the town dock and the Linden Point House, a 10 minute walk from the center of the village.

After our tour and a late lunch, we were back on I-95 and headed for home, much satisfied with our decision to see the Thimble Islands for ourselves at long last.


Photos by the author.

Written by Steve Hanley

Steve Hanley is a travel writer living in Rhode Island. I have traveled throughout the United States as well as Australia, Hong Kong, Europe and the Caribbean. I write about travel, automobiles and sustainability. Please follow me on Google + and Twitter.


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