Lifestyle / POSTED 21-Aug-2025;

Exploring Long Island Sound

WRITTEN BY: Gary Caputi
From the Southern Connecticut shore to Rhode Island’s historic Point Judith, you’d be hard pressed to find a more exciting place to enjoy boating. There are islands, quaint towns, tidal rivers, historic buildings and lighthouses, bird watching and great fishing for serious anglers or boaters who simply want to hang a baited hook over the side to catch dinner. Join us for a look at some of the places we have enjoyed over the years. 

Our first stop is the Norwalk Islands home waters of Yamaha pro angler and renowned fly-fishing guide Captain Jeff Northrop. Like many generations of Northrop’s before him, he grew up boating here and knows the coast and islands intimately. 

“The Norwalk Islands are a chain of twenty-five islands that stretch about six miles from the southwest to the northeast loosely paralleling the coast,” Jeff told us. “Created by the terminal moraine from the last ice age, the islands are close to shore, only about one to three miles, and an easy run from the Norwalk and Saugatuck Rivers. The various islands offer a range of recreational activities including camping, kayaking, swimming, bird watching and, of course, fishing. I strongly recommend you have the most up-to-date charts in your plotter before you head to these islands so you can avoid the seemingly endless boulders and shallows that surround them. In years past these hazards made the Western Sound notorious for dinged props and ruined lower units, but with the latest marine electronics those days are pretty much over.”

Norwalk - Serene Views of Long Island Sound and Sandy Shores in Connecticut.


The largest island in the chain is Chimon at 59 acres in the center of the chain and only a mile from the entrance to Norwalk Harbor. It is part of the Stewart B. McKinney National Wildlife Refuge, a disconnected group of protected areas that includes shorelines, marsh and island habitats. While much of the island’s shoreline is strewn with boulders, you can beach your boat at the three-acre beach at the northwest shore during the day. Access to the rest of the island is restricted from April 1 to August 15 during nesting season. No overnight camping is allowed. 

Cockenoe (pronounced “koh-kee-nee) is owned by the town of Westport and is Northrop’s favorite for its beauty and the site fishing for striped bass that can be found there in late spring. It is home to most of the bird rookeries in the chain with great blue herons, egrets, and black cormorants nesting there. Overnight camping is allowed by the Westport Conservation Department, but only four parties per night are permitted. Cockenoe has a shallow horseshoe shaped cove on its west side facing the mainland with a sand beach and beautiful scenery. It’s a great place to anchor, wade, swim and enjoy the environment.

Once called Ram, this 45-acre island was renamed Shea to commemorate Daniel Shea, a Medal of Honor recipient from Norwalk who died in the Vietnam War. Owned by the City of Norwalk, it connects to Sheffield Island at low tide. Both Shea and nearby Grassy Island are open to the public from May through Columbus Day with camping by permit. Two solar-powered restrooms are available in season, and there are 16 campsites. The entire shoreline is strewn with rocks and boulders, making it a more difficult place to approach by boat so caution should be exercised. 

Sheffield Island is the second largest island in the group, and the most southerly. Much of the shoreline is shallow and punctuated with large rocks and boulders with the exception of the lighthouse area so approach by boat requires caution. Many bird species nest on the island and it is one of the best places to see seals in the fall and early winter. It is also part of the Stewart B. McKinney National Wildlife Refuge and is controlled by the US Fish and Wildlife Service, which closes it to the public most of the year to protect the nesting areas. Public access is restricted to the 3.5 acres around the historic stone Sheffield Island Lighthouse. Built in 1868 and in use until 1900, the light is beautifully preserved and maintained by the Norwalk Seaport Association which arranges tours for the public during the summer months. There is a dock, small beach and picnic facilities with a dozen picnic tables under a large roof that provides a respite from the sun. 

The Norwalk Islands chain includes two dozen smaller islands that you can sail around, some privately owned so research which are private property before you consider going ashore. The entire chain and area shoreline is surrounded by rocky shallows and reefs that are home to commercially productive oyster beds. The oysters are considered to be the finest found anywhere in the country and Northrop family members are still involved in the oyster business today as have generations of Northrop’s before them.  

Thimble Islands

 
The Thimble Islands are found just off the coast of Stony Creek village in the city of Branford, Connecticut. This mini archipelago includes twenty-five small rocky, wooded islands topped with Victorian-era summer cottages replete with gingerbread trim. The sheer beauty of these tiny islands is akin to entering a different world in a different time.  While many of the islands are privately owned, the laidback homeowners co-exist with the kayakers, boaters, paddle boarders and sightseers in what is a relaxed atmosphere. The islands differ from most in the Western Sound because they are comprised of pink granite bedrock which gives the exposed areas an almost surreal appearance. 

The largest of the Thimble Islands is Horse Island at 17 acres. It is owned by Yale University and maintained as an ecological laboratory by the Peabody Museum of Natural History. Money Island at 12 acres is the second largest and is home to an entire village of thirty-two houses and a library. Governor Island is next and has fourteen homes while Rogers Island is one of several owned by billionaire Ray Dalio. Bear Island was home to a granite quarry that mined and exported high-quality pink granite to such construction projects as the Lincoln Memorial, Grant’s Tomb and even the base of the Statue of Liberty.  Davis Island was President William Taft’s “Summer White House” during his presidency, and Outer Island is part of the Stewart B. McKinney National Wildlife Refuge and can be visited during the summer season when volunteers conduct nature tours. 

Further north, off the coast of Gilford, Connecticut is Falkner Island, a three-acre rock that has been home to a historic lighthouse erected in 1802 commissioned by then President Thomas Jefferson. The beautifully maintained lighthouse is the second oldest in Connecticut. It was automated in 1978 and continues to operate as a navigational aid to this day. The island is also part of Stewart B. McKinney National Wildlife Refuge and hosts one of the largest nesting colonies of the endangered roseate terns in the country. The light keepers house is currently used by the USFWS for studying the birds. A few hundred yards to the south are the remnants of Goose Island now broken into three parts by erosion. We’re told the lush vegetation swept by the tides makes for a beautiful place to enjoy the sunset.

Fisher Island


As we approach Connecticut’s border with Rhode Island we find the largest island in the Sound. Fisher Island is nine-miles long, one-mile wide and is part of Southold Township, New York even though it is much closer to Connecticut, barely two miles off its coast. The history behind that claim dates back to colonial times and a dispute among noblemen but that’s a story for another time. Fisher Island is easily reached from the Thames River in New London, the Mystic River and the historic Mystic Seaport and from Watch Hill, Rhode Island. The island is known for its beautiful coastline and foliage and has two large sand beach areas. The Sound side has a harbor and large coves that make for sheltered access, anchorages and picnic areas. Fisher is the only island we’ve covered that is exposed to the open Atlantic on its eastern shoreline and as a result it has been ravaged by hurricanes and storms numerous times in its history. One such storm wiped out buildings and took down nearly every tree on the island but one hundred years later the trees had regenerated, and the island is beautifully forested once again. It has a small year-round community that swells to several thousand during the summer months. 

At the island’s western tip is the imposing Race Rock Light. This impressive granite lighthouse erected on a mostly submerged ledge that juts from the island, it was completed in 1878 after seven years of determination on the part of the engineers and builders. Strong, fast currents at this location (hence the name The Race) and conflicting seas are the normal conditions here where Long Island Sound, Block Island Sound and Fishers Island Sound all meet. Due to the large losses in lives, ships and cargo on the ledge over the years it was decided that a lighthouse was essential regardless of the difficulty and expense in building it. The Race is equally famous for the massive striped bass that are caught there each season so if you plan to go there bring along some ample fishing gear. 

Mystic Seaport

With Fisher we bring our island-hopping tour to an end but there is much more to see. If you’re in the area, Mystic Seaport, which catalogs the history of boating and sailing in the New World, is a wonderful place to visit by boat. A little further northeast is Point Judith and its namesake historic lighthouse that sits on a promontory overlooking the waters where Long Island Sound meets Narraganset Bay and the open Atlantic. The historic fishing port of Galilee is still home to an active commercial fishing fleet. The Point features a sheltered refuge for boats behind miles of breakwaters, pristine beaches, a few wonderful eating establishments and so much more. We hope our introduction to the wonders of Western Long Island Sound will provoke your adventurous side and get you on the water to explore this diverse region that is truly a boater’s paradise.
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