Day Trip: Thimble Islands, CT

IMG_4714Let the countdown to Memorial Day begin!

My favorite time to live in this blue state will be here in just a couple of weeks. And, while most people are already familiar with Fairfield County’s beaches, just a half an hour east of New Haven is a the little archipelago known as the Thimble Islands.

Once known as the “The Hundred Islands” twenty five tiny, rocky islands dot the Long Island Sound, and although they are entirely inhabited by private owners (except Outer Island, an ecological preserve), and only accessible via private boat, it’s a great choice for a unique New England day trip, or a stopover on your way to the Cape.

Thimble Island CTSuggested Itinerary:

Getting to the Thimble Islands is easier than you might imagine. Driving is always an option, but public transportation is also a viable option.

Take the Shore Line East train to Branford and it is a short (and inexpensive) cab ride from there.

If you’re coming from New York City, you can take the Metro North train to New Haven and transfer to the Shore Line from there. 

Once you arrive, enjoy lunch where the islands get their namesake, The Thimbleberry. This local favorite is right in Stony Creek village and serves traditional American cuisine such as burgers, homemade soups, and locally made ice cream. 

After lunch, enjoy a relaxing 45 minute tour of the islands on Captain Bob’s Thimble Islands Cruise.IMG_4725

Operating daily (except Mondays), Captain Bob Milne is a longtime resident of Stony Creek, and is extremely knowledgeable about the islands and their (sometimes) famous residents. 

IMG_4727You’ll get up close to the beautiful Victorian-era summer cottages, and learn more about the natural flora and fauna of the area. Tickets for this tour are just $12 (cash only) and advance registration isn’t necessary.

Now that you are cooled off from the boat ride, it’s the perfect time to hit the beach. 

IMG_4717Stony Creek Beach is open to the public, and just a short walk from the dock. Here you can swim (lifeguards are on duty), enjoy a picnic, and launch a kayak or canoe for a closer look at the islands.  

After visiting the beach, I recommend getting out of the sun for a while and visiting the Thimble Island Brewing Company, just a 10 minute drive away.

Sample their seasonal brews along with their year round classics, because this beer is not easy to find outside of Connecticut. 

When you’ve had your fill of Thimble’s offerings, drive another minutes to the beautiful Stony Creek Brewery right on the shore of the Branford River. 

Stony Creek’s beer has big hop flavors and is perfect for the craft beer aficionado of your group. 

IMG_4715As the sun begins to set, this would be a good time to call it a day, or if you’ve had too much to drink, settle down for the night at the Thimble Islands Bed & Breakfast. This inn offers gorgeous panoramic views and comfortable guest rooms, and guarantees a delicious breakfast the following morning. 


1 Comment
  1. During the Victorian era, the Thimble Islands were hopping with people traveling on steamboats from New Haven to day trip or spend a weekend at one of the island hotels that sprung up during that period. At one point, there was such a demand for islands that people began building manmade ones.

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