Cruising Stories

Cruising Connecticut's Eastern Shoreline


After living full time aboard TAPESTRY, our Kadey Krogen trawler, for well over six years, we’ve become dirt dwellers again. We returned to New England to resume seasonal cruising where the opportunities are varied and beautiful, the climate is temperate, and harbors are within easy reach. Eastern Connecticut is a part of this area, and where we’ll take a mini cruise in this article.

Starting Point: Old Saybrook, CT

We start our cruise in Old Saybrook, at the mouth of the Connecticut River. Whether you dock at Saybrook Point or pick up a mooring in North Cove, there are wonderful inlets and rivers to kayak, row or dinghy around on both the Old Saybrook and Old Lyme shores. The birds here are varied, many making this area their permanent or seasonal home.

At Saybrook Point, just north of Saybrook Point Resort & Marina, a town park lies on the river offering a great place to fish and picnic. If you’ve just transited from the south or north, Old Saybrook offers good provisioning options and availability of marine services. In addition, you’ll find many restaurants, shops and the Katherine Hepburn Cultural Arts Center.

Essex River Entrance

Stop 1: Essex, CT

Estimated Mileage: 5 NM

Essex is an historic and charming little town situated upriver, an excellent choice if the seas are up on Long Island Sound. Dock space and moorings are both available from the yacht club and marinas. As you head north on the Connecticut River past the Rt. 95 bridge, Calves Island will be on your right. This island is a bird heaven where you can even spot bald eagles. Every fall, around 400,000 tree swallows congregate here from all over New England to feast on insects in the reeds for a few weeks before starting their migration to Cozumel, Mexico. It is an amazing sight and draws many to anchor or kayak over from Old Lyme for the sunset ballet. Swallows fly in every night. Right before the sun sets, they disappear up and then dive down into the reeds in a tornadic display.

The village is comprised of many delightful shops, art galleries and restaurant choices along Main Street, where The Connecticut River Museum is also located.

Stop 2: Fishers Island, NY

Estimated Mileage: 24 NM

At the eastern most point of Long Island Sound lays Fishers Island, which is actually part of Southold, in Suffolk County, NY. The designation is only political as the island’s ties are with Connecticut. For example, the only ferry service from the island goes to New London, CT, the high school sports teams play only Connecticut teams, many island kids attend school in Connecticut, trash from the island goes to Connecticut, and the residents harken mostly from old New England gentry.

West Harbor offers some moorings for rent inside the breakwater and anchoring is good outside. Dinghies are allowed to be left by the yacht club. Most of the island’s eastern end is gated and composed of old mansions owned by the DuPonts, Rockefellers and other old-money families, as well as a prestigious golf course and the Fishers Island Club. The western end provides interesting rural roads where you’ll find a vegetable stand and Toppers, the island’s ice cream parlor, along with a hardware store and small grocery.

Mystic, CT.

Stop 3: Mystic, CT

Estimated Mileage: 5 NM

Located on the Mystic River, Mystic is a village in the towns of Groton and Stonington. Shipbuilding was a significant endeavor, with more than 600 ships built here in the late 1700s. Mystic Seaport depicts that era and has docks available for transients. Anchorage for a few boats is also just north of the seaport. Docking at the Mystic Seaport Museum is a real treat. Not only are the exhibits educational and fun, but while docked you enjoy access to the grounds even when the museum is closed. It’s magical, especially for kids.

Farther downriver, a bascule bridge crosses the road in the hamlet of Mystic. Many marina choices are nearby, allowing dinghy and kayak access to town and the museum. The town offers a wide variety of excellent restaurants as well as an art museum, local history and old New England architecture. If you’re heading upriver and have a hankering for seafood, Abbott’s Lobster in the Rough is on the western shore of the lower end of the river and has transient dockage. Just keep an eye on your plate as the seagulls get hungry, too!

Stop 4: Stonington, CT

Estimated Mileage: 3 NM

Stonington was voted one of the “Top 10 Prettiest Coastal Towns in New England” by Yankee Magazine. Get a mooring or dock space from Dodson Boatyard, and you’ll be right in the heart of the Borough. The harbor is mostly protected by a breakwater from the fetch across Fishers Island Sound where it joins Block Island Sound.

After a short launch ride to shore, you’ll see eclectic shops, beaches for swimming and sunbathing, The Lighthouse Museum for exploring the area’s maritime and agricultural history, and many restaurants offering fresh, seaside dining. A walk to the point of the peninsula offers panoramic views of New York, Connecticut and Rhode Island, as well as a rosy sunset.

Stop 5: Watch Hill, RI

Estimated Mileage: 3 NM

Watch Hill, RI.

Full disclosure, Watch Hill is actually a village in Westerly, RI. It is included here, because it is accessed by water from Fishers Island Sound. The entrance to the harbor is a long and narrow one east of the Stonington Borough peninsula. It is protected from Block Island Sound by Napatree Point, a 1.5-mile-long sand spit extending west of the Watch Hill business district. Napatree is the southernmost and westernmost point of mainland Rhode Island and is a wildlife preserve and popular beach.

Watch Hill, or Napatree as it’s often referred to by boaters, provides a large harbor area where many raft up for a summer weekend. A word of caution, it is open to the southwest, so avoid anchoring when storms approach from that direction. A walk on the Point will offer exercise, gorgeous views and lots of bird sightings, many spending time here while migrating.

In town is the Flying Horse Carousel, the country’s oldest suspension carousel, built in 1876. The ponies are hand carved, with leather saddles and real tails and manes. Kids love trying to catch the brass rings as they ride. St. Clair Annex offers locally made ice cream and great gelato. If you’re looking for old-fashioned luxury, a visit to the Ocean House is a must. There you’ll find a lovely old-school croquet court with a Croquet pro, a private beach with cabanas, wine tastings, and pastel- colored bikes and Mercedes vehicles for guests to explore the area in style. But even if you never leave your boat, Watch Hill is a wonderful place to visit.

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