Old Saybrook, CT to Gardiner's Bay, NY

Explore the Longest River in New England

New England

THE CONNECTICUT RIVER, one of only 14 American Heritage Rivers, is the longest river in New England, beginning north of the Vermont/Canadian border and ending its flow more than 400 miles later in Old Saybrook, CT, where it spills into Long Island Sound. The estuary at the mouth of the river is graced with grassy marshes and woodlands, migrating birds and ongoing beauty. The sandbar here impeded industrialization and, as a result, it has remained a wonderful and natural watershed.


This idyllic place, originally as shallow as its Old Saybrook counterpart, South Cove, has been dredged by the U.S. Army Corp of Engineers since 1969. Their purpose has been to provide a harbor of refuge between Point Judith, RI, and New Haven, CT. The dredged area accommodates about 150 boats, whose owners have waited on a list at Old Saybrook Town Hall for up to 10 years for a mooring assignment. Anyone may come into the cove and pick up a vacant mooring with a yellow tag for up to 48 hours, at no charge.

The Cove is bordered by private residences, a town boat ramp, a town dock with water and the North Cove Yacht Club. For a nominal fee, launch service and use of the yacht club facilities are available to visitors.

Aerial view of North Cove Yacht Club | Old Saybrook | Marinalife
Aerial view of North Cove Yacht Club

From the shore, a nice walk up Sheffield Street intersects with Main Street. Here you discover shops, restaurants, groceries, liquor and the Katharine Hepburn Cultural Art Center. Walt's Food Market, where Kate herself shopped, has provisions and delicious sandwiches and soups. Liv's Oyster Bar offers fabulous dinners, Penny Lane Pub is a local gathering spot and Jack Rabbit's serves delicious hamburgers. The Old Saybrook Chamber of Commerce Visitors Center at the Rt. 1 Junction provides any assistance you may need.


North Cove to Coecles Harbor - 17.2 NM

As you leave the Connecticut River, cross the eastern most end of Long Island Sound, and enter Gardiners Bay, which separates the North and South Forks of Long Island, NY. The passage into the bay is called Plum Gut, marked to starboard by the Plum Gut Lighthouse (affectionately named The Coffee Pot, owing to the boiling water often encountered in the Gut as the depth changes from 323 feet to 67 feet).  To port is Plum Island, a U.S. government facility and site of the Plum Island Animal Disease Center and the former U.S. military installation, Fort Terry. When wind opposes tide in Plum Gut, it is challenging. Mariners should plan accordingly and realize this is not the place for a small vessel.

Just inside the channel to Coecles Harbor to port is the anchorage. Excellent holding in mud and good protection make this a relaxing weekend destination. While there, dinghy over to Taylor's Island, owned by the Taylor's Island Foundation. You find a dinghy dock, and visitors are welcome. The island gives dogs a place to run, and you can learn a lot about this historic cabin and its restoration.

Just beyond Taylor's Island, in the southwest corner of the harbor, head into Congdon's Creek by dinghy or kayak and explore. More kayaking and hiking trails are in the Mashomack Preserve, located in the southeast section of the harbor in the anchorage area. The beaches at either side of the channel, Reel Point to the north and Sungic Point to the south in the preserve, are wonderful shelling beaches.

Dockage and mooring are also available at Coecles Harbor Marina. Anchoring boats pay to dock their dinghies here and take the less than one-mile walk to The Whale's Tail Ice Cream and Mini Golf. Another shoreside option is a stroll from the marina to the ferry to Greenport and lunch at Claudio's.

For a special evening, make a reservation for dinner, or drinks and tapas on the lawn, at the Ram's Head Inn. This gorgeous inn has operated since 1929 and offers fine dining to the public. It is located on Ram's Head, adjacent to the anchorage, with dinghy docking on site.


Coecles Harbor to Sag Harbor - 4.6 NM

A short cruise from Coecles Harbor to Sag Harbor provides a very different, yet appealing destination. You enter the Peconic River at Cedar Point, marked by the historic Cedar Island Lighthouse. Following the twisting channel, you arrive in Sag Harbor Bay and the Village of Sag Harbor, part of both Southampton and East Hampton. Megayachts dock here, but many weekend cruisers dock, take a mooring or anchor here as well. A range of services are available from pump out, fuel, launch service and dinghy dock to provisions, restaurants, Amtrak and airport.

Relaxing at anchor in Sag Harbor Bay

On shore, the visitor's center is a few steps away inside a windmill and leads up to Main Street. The Hamptons is filled with unique boutiques, but you can also find one of the best hardware stores around. At the top of Main Street, the road forks. To the left is Il Capuccino Ristorante, an authentic old-world Italian restaurant, which is often our main reason for coming to Sag Harbor. The town has a history rich in whaling that can be explored after the road forks to the right at the Sag Harbor Whaling and Historical Museum.

Dinghying or kayaking past the dinghy dock presents an enjoyable exploration and brings you to Foster Memorial Town Beach or around Brush Neck into The Little Narrows and Morris Cove. Havens Beach, by the Sag Harbor Bay anchorage, is also a nice spot for swimming and picnics.

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