New England’s Smallest Islands – The Thimble Islands

Every year for many years I’ve blasted down Highway I-95 in Connecticut, frequently passing by a little sign near Exit 56 which states, quietly and simply, Thimble Islands. What are these “thimble islands” I would wonder, as the sign blurred by and the years moved on. I had heard on the street that these little land masses consist of many small rocks jutting out of the Long Island Sound and that throughout the generations many people have built homes atop them. Finally I had heard enough. As an island lover, I decided that I must see for myself these tiny islands so near where I live.

A few Thimble Island cruises departing from the mainland village of Stony Creek take passengers around the islands throughout the summer months. You must be content to stay on board, as most of the Thimble Islands which are inhabited are individually owned, making it almost impossible to step ashore without an invite. Twice I have gone on a Thimble Island cruise, both times motoring out onto the Long Island Sound aboard the Volsunga IV with Captain Bob, who navigates around the hundreds of masses of rocks, all the while telling tales of history and modern-day life ashore.

A lone, unoccupied Thimble Island with a seagull on top

This Thimble Island is apparently inhabitated by a lone seagull

The number of Thimble Islands varies from around 100 to over 300, depending on the tide and on how big a rock must be before you can declare it an island. Only 23 of these large pebbles are inhabited, holding a total of approximately 85 homes. By far the most populated is Money Island, an upper middle class community of about 30 families. On the majority of the rest of the populated islands stand just one house, allowing the home owner the very cool right to say “I own an island.”

Only seven islands have electricity, courtesy of underwater cables. Most homeowners prefer to do without, so they can experience the same peaceful life as did inhabitants in years gone by. The Thimble Islands weren’t always 100% silence and tranquility, though. This section of the Long Island Sound was a very happening resort area in the early 20th Century. Then in 1938 the New England Hurricane took its 30-foot waves and wiped the resorts right off the rocks. Not in the mood to rebuild, the rich began partying on Cape Cod instead.

Cut-n-Two East and Cut-n-Two West, the Thimble Islands

Cut-n-Two West and Cut-n-Two East

The hurricane of 1938 also caused the division of an island called Cut-n-Two, when its waters and winds destroyed a little wooden footbridge that hooked together two pieces of land ever so slightly separated across a narrow slice of water. To this day the bridge has not been rebuilt and the two land masses stand just outside of each other’s grasp. Before the hurricane tore the bridge asunder, on shore dwelt a lady named Little Miss Emily, a dwarf performer with P.T. Barnum’s Circus. General Tom Thumb, a fellow dwarf, quite loved Miss Emily and courted her mightily on Cut-n-Two. Unhappily, their relationship floundered and, like the island, they parted ways.

Gazebo for sale on Demijohn Islands, the Thimble Islands

For Sale - $375,000 Gazebo (island included)

My favorite Thimble Island is Demijohn Rock a/k/a Cedar Rock. At some point, someone wanted to build here, very badly. Alas, this speck of stone was too minute for a house. Dreams can die hard, though. Instead of a house, the would-be island home owner erected a wooden gazebo. I noticed it for sale last year on my first Thimble Island cruise, and this year I saw it again, a victim of the real estate market. $375,000 is its asking price, which really is quite reasonable for island real estate, I think.

I heard these stories from Captain Bob, who is a great teller of tales. The ever-changing tide causes him to navigate different courses on each Thimble Island cruise, sharing the stories of whichever islands he happens to pass. If I go on enough of these Thimble Island cruises, I think eventually I’ll be able to piece together a complete picture of these tiny islands in the Long Island Sound

13 Comments Post a Comment
  1. Soundbounder says:

    Such a beautiful place, and IMO the tours remain a great bargain.
    Also, I learned last year that Outer Island is open to the public on weekends during the summer months. I need to make that trip one of these days.
    Soundbounder recently posted..Clouds In The SoundMy Profile

  2. Gray says:

    OMG, what a riot! “Let’s buy an island….and build a gazebo there!” Who the heck would pay $375K for an island too small to even build a house???? Crazy.
    Gray recently posted..Perspectives on Long-Term Solo Female TravelMy Profile

  3. Sabina Lohr says:

    Really? I’ve never heard of Outer Island. I would like to check that out.

  4. Sabina Lohr says:

    I suppose someone who really, really wanted to own an island.

  5. Mike says:

    Ah, Island Life just nothing in the world like it. I just made sure I settled on one with a nice hill to keep my about 300 feet above sea level.

  6. Suzy says:

    What an interesting grouping of islands with even more fascinating stories behind them. I love the gazebo photo.
    Suzy recently posted..Girne, North Cyprus Wishes You Were HereMy Profile

  7. Sabina Lohr says:

    They really are cool. I’m so glad I finally checked them out.

  8. Sabina Lohr says:

    Ha – that sounds smart! The tide will never make your island disappear.

  9. Bali Huts says:

    Beautiful. I would love to live on an island like that, so peaceful.

  10. Sabina Lohr says:

    Yep, very peaceful.

  11. Bob says:

    This sounds like some of the islands in Miami. I’m so intrigued, who do I need to befriend to be invited to land?

  12. Sabina Lohr says:

    Hi, Bob. You need to know someone who lives on one of the islands. Or someone who knows someone who knows someone…

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