What do Ayn Rand, President William Taft and Tom Thumb have in common?
They all shared an affinity for a small slip of Connecticut known as the Thimble Islands.
Unsuspecting travelers can easily miss the chance to explore one of the most unique Connecticut attractions. And yet those in the know can tell you what to do on the Thimble Islands.
That is, if they wanted to welcome you into their fold.
Read on for our guide to what is without question one of the most exclusive and unique of Connecticut’s many attractions.
A Brief History of the Thimble Islands
The Thimble Islands is the largest group of islands in Connecticut.
Anywhere from a hundred to 365 islands make-up the archipelago, depending on whether you count outcroppings like:
- Sand bars
- Small rocks
Located off of the Stony Creek area of Branford, the islands were named after the abundance of thimbleberries that grew wild here.
Before Europeans arrived, the Mattabesek Indians used the islands as summer camping grounds. Their name for the archipelago was Kuttomquosh, “the beautiful sea rocks.”
The Thimble Islands in the Colonial Era
Adrian Block, a Dutch explorer, was the first European to discover the islands in 1614. And yet it was not until 1716 that colonists claimed land grants of the islands. Colonial owners occupied the last of the islands by 1773.
During the colonial period, local farmers treated the islands as a source of seaweed, for fertilizer.
That said, commercial fishing remained a major form of commerce until World War I.
Oyster connoisseurs celebrate Stony Creek oysters, pulled from these waters.
The Thimble Islands as Connecticut’s most exclusive resort destination
By the mid-1800s, the islands became a tourist attraction with steamboat excursions and a hotel.
On his Pot Island property, local resident William Bryan built the Thimble Island Hotel in 1846. Bryan drew both tourists and treasure hunters by exploiting the legend that Captain Kidd buried his treasure on the islands. Within a month, day-trippers flocked to the steamer Hero for tours of the islands. Bryan expanded his hotel the following summer, adding two bowling alleys, boating, swimming, and fishing. The railroad that ran between New Haven and New London in the 1850s made the trip convenient for those living in nearby cities. The islands became a popular resort area offering a respite from busy city life.
Within a few decades, people were building homes and cottages on the highly desirable shores of the islands.
Changes were most notable following the war, including laying:
- Water pipes
- And telephone cables
The Thimble Islands continue to provide a safe haven for weary people looking for a place to escape. Provided no winter storms or hurricanes are headed their way, anyway.
That said, many of those who summer here occupy small summer cottages passed down from generation after generation. There are a total of 81 houses on the inhabited islands:
- There is only one house on each of 14 of the islands. Rogers Island has a 27-room Tudor mansion, tennis and basketball courts, and a caretaker’s residence on its 7.75 acres.
- Governor Island has 14 houses
- Money Island, measuring 12 acres, is home to an entire village of 32 houses, a church, and a post office, all hidden among tall trees
- And the rest have between two and six houses
Of the inhabited islands, only six islands get electric power delivered via underwater cables.
Things to do on the Thimble Islands: 9 Top Picks
With a bit of the archipelago’s history in hand, what is there to do on the Thimble Islands?
Quite a bit, provided you’re looking for a destination more akin to Maine than a location a short drive from New Haven and New York City, for that matter. Before you plan your day trip to one of most unique spots in Connecticut, check out the most popular activities.
Take a Cruise on the Sea Mist Thimble Islands Cruise
Thimble Islands cruises take you out on open waters. There, you can appreciate the distinctly mauvish hue and dotted land that makes up this iconic American vacation spot.
After all, the only way to know you’re on an island is to see it from the water!
The Sea Mist is located at the Town Dock in Stony Creek Harbor. Their boat tours are the best way to see the wondrous line of islands.
You’ll hear lofty stories, both rumored and confirmed, that took place on the islands. Some of the most interesting include:
- The possibility of Captain Kidd hiding his treasure here
- Tom Thumb’s favored dating spot on Cut-In-Two Island
Some of the island names alone can provide entertainment for your cruise.
Meanwhile, the sheer opulence of other islands are a tribute to the pursuit of happiness.
Case in point: Rogers Island.
This 7.5-acre private island is the backdrop for an 8,746-square-foot Tudor mansion, with tennis and basketball courts, a caretaker’s residence, and a putting green that Jack Nicklaus designed himself.
And of course, there is Davis Island, the cherished summer spot of President Taft.
Take the Thimble Island Ferry to the Stewart B. McKinney National Wildlife Refuge
You’ll find Stewart B. McKinney National Wildlife Refuge on the outermost Thimble Island, appropriately named Outer Island.
Southern Connecticut State University uses Outer Island for ecological research. And during the summer months, Outer Island is both open to the public and staffed with volunteers.
Here, you’ll discover why another name for the Thimbles are the pink granite islands. You can take in the majestic pink boulders and unusual cobblestone beach as well as spot birds and waterfowl who call the island home.
Get away from it all and spend quality time with nature, all while taking impressive selfies of yourself at one of the most beautiful spots on Earth.
Hop on the other Thimble Island ferry service, Volsunga IV, to hit-up this wildlife refuge.
Paddle Around the Thimble Islands
If you’re feeling particularly sporty, a perfect way to explore the islands is by kayak. You can spend a few hours taking a leisurely 4-mile paddle so relaxing it won’t feel like exercise at all.
Provided there’s no wind, at least.
Arms tired? Pull up at a quiet spot to take in the beauty of the area.
A few local outfitters for paddling and kayak rentals include:
Visit Stony Creek Quarry
With so much pink granite around, it’s no surprise that in the mid-1860s a few thousand people made a living at the flourishing rock quarries. Here they toiled, removing the highly prized granite, processing and carving it to bring out its pink speckled beauty.
Architects viewed it as a highly durable material with a unique undulating veining that made it seem alive. The pink granite graces many American landmarks including:
- The Statue of Liberty
- The George Washington Bridge
- Grand Central Station
The allure and hard work of the island quarries drew author Ayn Rand to the area when researching stone works for her book, The Fountainhead.
Lucrative offers for prime waterfront land were too tempting for many former quarry owners to pass up.
Stony Creek Quarry hosts the sole surviving quarry here today.
Stop By the Stony Creek Museum
Curious to learn more about the history of Stony Creek and the Thimble Islands?
Then while visiting Stony Creek Quarry, be sure to visit the Stony Creek Museum. It is the perfect way to finish your day with some well-rounded information about the quarry and insights into life in a quaint Connecticut coastal village.
Bask in the Sun on Stony Creek Beach
The beach might be tiny, but it’s a lovely spot to get your beach bunny groove on.
Don’t forget a book, mysterious sunglasses, a sexy broad-brimmed hat à la Katharine Hepburn, and some cool drinks on ice.
Some other great nearby Connecticut beaches include:
- Jacobs Beach, in Guilford
- Hammonasset Beach State Park, in Madison
- Clinton Town Beach
- Harvey’s Beach in Old Saybrook (Ms Hepburn’s favorite haunt)
Admire the Granite Detailing at Willoughby Wallace Memorial Library
A visit to the Willoughby Wallace Memorial Library provides the perfect opportunity to see why pink granite became such a high-demand architectural detail.
At risk of beating a dead horse about the local pink granite, it truly is lovely. And the library is a perfect refuge if it happens to rain during your visit.
Set in until the storm passes, curled up in a comfortable chair with a book, and you will have found your slice of heaven. You can also take a peek at the tiny, impressive art gallery in the foyer.
Buy a Thimble Island souvenir or two
I love punny business names as much as the next hipster.
If the name alone isn’t enough to get you to drive out to Taken For Granite, the unique souvenirs and thoughtful displays should do the trick.
And if you’re not up for a drive, Seaside Home and Gifts is worth a browse to find not just gifts, but housewares and clothes. A close neighbor to the Stony Creek Market you’re sure to find something for someone – even if just for yourself. Don’t forget to grab a slice of pizza at the market or enjoy one of the assorted dishes prepared fresh every day.
Hop on Over to Stony Creek Brewery
Craft beers are all the rage today, and the Branford River waterfront is home to the Stony Creek Brewery. There’s plenty to do to while away a few hours:
- Sample artisanal beer at their indoor-outdoor taproom
- Grab a bite at their cleverly planned rotating array of food trucks
- Play games at their game pit
This top Connecticut brewery is a great place to end your Thimble Island day trip.
Keep exploring the Connecticut shoreline
With a day trip to Stony Creek and the Thimble Islands in the bag, what’s next?
Keep planning your visit to the Connecticut shoreline, some excellent nearby points include:
- Yale University and more attractions, activities, and things to do in New Haven, Connecticut
- More charming Connecticut towns in New Haven County
- Discover the best beaches in Connecticut
- And find even more unique and quirky attractions in Connecticut, from Greenwich to Stonington, in our Connecticut Travel Guide
And for a local’s introduction to another exclusive section of Connecticut, explore our guide to things to do in Greenwich, Connecticut.