Essex

We walked into Essex from the parking lot on Main Street and Lia stopped almost immediately, phone half-raised, at the sight of a white Federal-style house with black shutters and a widow’s walk facing the river. It turned out to be one of dozens — Essex has one of the best-preserved concentrations of colonial and Federal architecture in New England, a legacy of the shipbuilding wealth that once flowed through this bend of the Connecticut River. Main Street runs gently downhill toward the water, lined with elms and gift shops and the kind of general store that still sells penny candy from glass jars, ending at a marina where sailboats bob against a backdrop of tidal marsh.

The waterfront and the Connecticut River

At the foot of Main Street, the Connecticut River Museum sits on a dock built where, in 1776, American colonists launched the Turtle — the world’s first submarine used in combat — against a British warship in the harbor. We wandered the small exhibit and then out onto the museum’s own dock, where the river widened lazily toward Long Island Sound and ospreys worked the shallows. Essex has been a boatbuilding town since the 1700s, and that heritage is still visible in the yacht yards and sail lofts lining the shore; we watched a wooden Herreshoff sloop glide past, its varnished hull catching the afternoon light, looking like it had sailed straight out of another century.

The Essex Steam Train and river marshes

The next morning we boarded the Essex Steam Train, a vintage 1920s locomotive that still runs on the old Valley Railroad line, hauling wooden coaches north through tidal marshland thick with egrets and red-winged blackbirds. The engine hissed and clattered exactly as it must have a century ago, cinders drifting past the open windows, and we connected at Deep River Landing with a riverboat cruise up to the Gillette Castle bluffs before looping back. It was unabashedly touristy and we loved every minute of it — Lia said it was the first time a train ride had made her nostalgic for an era she’d never lived in.

Getting There

Essex sits roughly halfway between New York City and Boston, about a two-and-a-half-hour drive from either via I-95 and Route 9. Amtrak’s shoreline service stops in nearby Old Saybrook, ten minutes away by car or taxi, and Bradley International Airport near Hartford is the closest major airport, about fifty minutes north. The village center itself is compact and best explored on foot, with the steam train depot in neighboring Essex station and the harbor just a short stroll from Main Street.