Essex -The Perfect American Small Town

A dignified, Revolutionary War—era spirit lingers in Essex, a mint-condition one-traffic-light village on the Connecticut River, where early colonial and federal houses tell of the town’s shipbuilding heyday. On Main Street, white picket fences frame many landmark buildings, a mix of grand private homes and specialty stores.

You can learn about the town’s seafaring heritage at the waterfront Connecticut River Museum, which sits 5 miles north of where the river empties into Long Island Sound. It comprises an 1870s steamboat warehouse filled with ship models and maritime artifacts, including a full-scale replica of America’s first submarine, The Turtle, built during the Revolutionary War. Train buffs will enjoy touring the lower Connecticut River valley in vintage 1920s Pullman cars, riding the Essex Steam Train north to Deep River, where passengers can either return to Essex by train or continue aboard a three-deck Mississippi-style riverboat to East Haddam.

One of the most celebrated buildings in Essex is the Griswold Inn, the oldest continuously operating inn in Connecticut. Opened in 1776, the “Gris” is most famous for its Tap Room, originally the town’s schoolhouse, built in 1738. A potbellied stove sits at its center, and its wood-paneled walls are lined with maritime memorabilia and original Currier & Ives prints. Much of the inn’s buzz (not to mention Dixieland jazz and banjo music) emanates from here. Overnighters can hang their hats in any of the handsome guest rooms; many lodgers stay for the weekend just to partake of the inn’s Sunday Hunt brunch, an enormous affair said to have been initiated by the British, who commandeered the inn during the War of 1812.

It’s just a few minutes’ drive inland to liny Ivoryton’s classic Copper Beech Inn, which occupies the former homestead of one of the community’s most esteemed merchants. The 7 acres of gardens are stunning, and the 13 rooms equally dazzling, many with soaring cathedral ceilings and deep tubs. Most of the rooms are in a handsomely restored carriage house, with just four in the Main House, also the site of a stellar restaurant, serving the likes of lobster bisque with shaved trulfles and pork tenderloin with blue-cheese mashed potatoes and fava beans.

You may experience a moment of century adjustment if you’re in the area mid-July, when nearby Deep River hosts its annual Fife & Drum Muster, said to be the largest in America. More than 70 units play their hearts out as they march down Main Street during the event’s three-hour parade of uber-Americana.