Travels with Sissy: Thimble Islands


Stony Creek Harbor on Long Island Sound is nestled in the southeast corner of Connecticut. The town of Branford is located off of I-95, and takes you back to a time of yesteryear with ice cream shacks, small town beaches and kids jumping off a pier- after a long bicycle ride in the hot summer months of New England.

The docks at Stony Creek are lined with small boats and some luxury ones too! The ships offering a cruise thru the Thimble Islands range from two-story boats with a snack bar & sanitary facilities, to one story with no frills attached. I went for the latter, and climbed aboard for the forty-five minute tour.


The Thimble Islands are made of pink granite bedrock. Before the last Ice Age, the islands were tops of hills. The European explorer, Adrian Block, first discovered the area in 1614. Legend has it that Captain Kidd also used Thimble Islands as a hiding place for his ships; some say, he even buried treasure there.

The islands vary in size, as well as the number of homes built on each island. The homes range in size from two room cottages, to mansions with living quarters for caretakers.


Home Island is the largest island consisting of 17 acres. It is owned by Yale University and is used as an ecological laboratory by Yale’s Peabody Museum of Natural History. Money Island consists of 12 acres, has 32 houses and a library. Governor Island consists of ten acres and has 14 houses. And then, there are the smaller islands with just one home.


Thimble Islands has contributed to our country’s history. The granite quarry on Bear Island helped to build the Lincoln Memorial, Grant’s Tomb, and the base of the Statue of Liberty.

Some famous residents of the islands include General Tom Thumb, Garry Trudeau, Jane Pauley, and President William Taft- who had a ‘Summer White House’ on Davis Island for two years. Most residents like & respect the privacy of the islands. It is ‘understood’ that no one docks on an island without an invitation. Today, many residents have their own boat, or sea plane for transportation. However, there is transportation to town every hour on the hour from 8:00 am to 8:00 pm. This water taxi service has been provided to the residents even before phones were installed on the islands; residents just left a red flag on a rock & the service would stop at their home.


They say no man is an island, but Thimble Islands has proven that wrong. The question is… would you want to live on a one acre island, in a two room cottage surrounded by water & rocks?


2 thoughts on “Travels with Sissy: Thimble Islands

  1. Dana Feero August 20, 2016 / 5:16 pm

    Hi Linda! I love this report on the Thimble Islands because my book, Fireflies of Swithmore Creek, is mostly set in upstate NY, possibly Long Island, I need a spot where there is a national forest, a creek, and a small town. Know any places like that?

    I like your writing style. It’s…cozy. Keep up the good work and God bless!


    • lindamassucci August 22, 2016 / 11:09 am

      Thanks for the lovely thoughts on my travel blog. I truly appreciate it! Good Luck with your writing!


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