Essex, Connecticut

Cruise one of America’s Best Small Towns and feel your blood pressure fall.

A quintessential New England small town on the banks of the tree-lined Connecticut River, Essex is a mix of white-picket-fence charm and colonial history, all with a heavy nautical overlay. Six miles up the river from Long Island Sound, Essex offers some protected and picturesque coves, an inviting Main Street, and a boating-centric culture that makes visiting cruisers feel more than welcome. Indeed, Essex today has more transient moorings for boats than it does parking spaces for cars. And if Essex itself isn’t enough of an attraction—even though it’s on almost everybody’s list of Best American Small Towns—then head up the river another mile and drop the hook in Hamburg Cove, one of the most protected and alluring gunkholes on the East Coast, if not the entire U.S.

Like many other great cruising destinations in the Northeast, Essex is easy to get to. On Long Island Sound, about six miles east of Duck Island Roads off Westbrook you’ll see the Saybrook Breakwater Light. It’s 58 feet high and on the end of a 1,000-foot-long breakwater. The wide channel between it and the matching breakwater to the east leads north up the Connecticut River to Essex, and then another 40 miles or so to Hartford, the state capital.

After the breakwater you’ll pass two large, full-service marinas off to port—Saybrook Point Marina and Harbor One Marina—and in two miles you’ll reach the Amtrak train tracks on the Old Lyme Drawbridge, with a vertical clearance of 19 feet. Contact the tender on Channel 13. Just north of the drawbridge is the I-95 car bridge, but it has an 81-foot vertical clearance.

This part of the river is rich in history. The Algonquin Indians fished and farmed here until 1590, when the more warlike Pequots from the north drove them out. The first

European recorded to have landed here was Adriaen Block in 1614 after he had explored Block Island farther east. Over the years, the small village of Essex grew and prospered because of its protected location with access to both Long Island Sound and to the increasingly productive Connecticut heartland. Essex also became a major shipbuilding center; by the time the Revolution ended Essex had launched some 600 vessels for the patriots.

But it was the War of 1812 that put Essex in the history books, largely as a result of one of the British Navy’s most successful raids of all time. During the war, Essex shipbuilders were busy producing privateers that attacked British ships in the Caribbean and western Atlantic. The British sent some warships to attack the town, but they couldn’t get past the sandbar off Old Saybrook. So on the night of April 7, 1814, 137 British marines rowed the 6 miles up the river on 6 well-armed boats, arriving off Essex at 3AM. The British captain in charge told the villagers that if they did not fire on his men he would not harm them, but he did intend to destroy all the privateers. Within a few hours, the British had burned 27 ships before rowing back down the river. For the past 46 years, Essex has honored this event with an annual Burning of the Ships Parade, complete with period uniforms and a fife and drum corps.

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Today, Essex (population 6,600) is a bastion of peace and tranquility. As you approach up the river, you’ll first pass the Essex Yacht Club and the Brewer Dauntless Marina on your port side, just north of marker R-26 in the middle of the Essex mooring field. Brewer has two first-class, full-service marinas in Essex. The first—Brewer Dauntless Marina—has 42 slips, a 150-foot fixed dock and 55 moorings with launch service. On your boat you’ll next pass the large Essex Island Marina—also a full-service facility—with 125 slips, a swimming pool and grills in a picnic area. Marley’s is a seasonal casual restaurant with carryout, plus breakfast and lunch all week and dinner on weekends. I’ve stayed at Essex Island Marina many times over the years, and when my children were younger they particularly enjoyed the 30-second ferry ride over the 20-yard passage to the mainland. Still heading north, the final marina is Brewer’s second facility in Essex—the Brewer Dauntless Shipyard—with 108 slips for boats from 20 to 100 feet, plus a swimming pool and all the usual first-class amenities. The Shipyard, as the name implies, is a major repair and maintenance operation.

Main Street is less than a five-minute walk from any of the marinas. You can’t go to Essex without at least stopping at the iconic Griswold Inn, which has been there since 1776. “The Gris” not only has a great taproom—rated as one of the best bars in America by Esquire—and restaurant, but it also has a major collection of marine art, with prints by Currier & Ives and Endicott & Co., and illustrations by Norman Rockwell.

For more casual dining, head up Main Street to the Black Seal Seafood Grille, one of my favorites, with a great bar (probably never mentioned by Esquire) and order a Dark and Stormy, a house specialty. The Black Seal also has memorable burgers, chili, and fish & chips, surrounded by fun nautical décor. If you want to pick up some delicious sandwiches or box lunches for the boat, go back down Main Street to Olive Oyl’s Carry Out Cuisine, a perfect spot for fast provisioning. In a white house almost next door, the Essex Coffee and Tea Company is the Essex version of a coffeehouse, with monthly displays by local artists. And if you want a casual breakfast, lunch or dinner with a waterfront view head back to Abbey’s Place just behind the Brewer Dauntless Shipyard.

When you’re through eating, walk down to the foot of Main Street to the Connecticut River Museum. You’ll find one of the best views of the river, great exhibits on shipbuilding and local geology, plus a full-size replica of the Turtle, the first American submarine, built by David Bushnell of nearby Westbrook in 1776.

For evening entertainment check out the Ivoryton Playhouse, a ten-minute cab ride away. Katharine Hepburn started there in 1931; it has also starred Eva Gabor and Marlon Brando. If you have more time, try the Essex Steam Train and Riverboat, which starts at the 1892 Essex train station and heads along the shoreline to Deep River Landing, where you climb aboard the Becky Thatcher, a three-deck Mississippi River-style riverboat for a ride farther up the river.

Before you leave the Essex area, cruise just a mile upriver to Hamburg Cove, with a narrow entrance east of Brockway Island. Drop the hook and feel your blood pressure fall; this is one of the prettiest and best-protected boating spots around. If you want to explore, you can follow the green markers to the end of the cove and find Reynolds Garage & Marine, a small freshwater marina. Mind the channel. I’ve bounced off the bottom there in my Grand Banks 36 several times, but I wouldn’t miss Hamburg Cove for the world.


Essex Island Marina
(860) 767-1267 • 

 Brewer Dauntless Marina
(860) 767-8267 •

  Brewer Dauntless Shipyard
(860) 767-0001 •

  Reynolds’ Garage & Marine
Lyme, CT
(800) 899-0028 • 

Griswold Inn
(860) 767-1776 •

 The Black Seal Seafood Grille
(860) 767-0233 •

 Olive Oyl’s Carry Out Cuisine
(860) 767-4909 •

 Essex Coffee & Tea Company
(860) 767-7804 •

 Abby’s Place
(860) 767-0560  •

 Connecticut River Museum
(860) 767-8269 •

 Essex Steam Train & Riverboat
(860) 767-0103  •

 Ivoryton Playhouse
(860) 767-7318  •

Peter A. Janssen, Southern Boating July 2014