The historic village of Essex, Connecticut, has long served as a favorite stopover for coastal cruisers in New England, given its location just five nautical miles from Long Island Sound. Built around a trio of coves tucked into the western shore of the Connecticut River, Essex is home to three marinas and a yacht club, all of which offer transient slips and dockage for large vessels (moorings are also available). It’s a boater-friendly place, for sure, and Essex officials like to boast that the town has more slips than parking spaces.

Steps from the waterfront, pleasant tree-lined Main Street is home to an eclectic array of boutiques, gift shops and stores, as well as several places to dine. Chief among these is the Griswold Inn, which has been serving mariners since 1776 and is the oldest continually operating tavern in the country.

There’s plenty to do and see in and around Essex, starting with the excellent Connecticut River Museum, directly on the waterfront. The grounds are a lovely spot to relax and take in the river, while inside you’ll find fascinating exhibits on the history of Essex, including the 1814 British raid on the village and a replica of the first submarine ever built. Other exhibits explore the river’s former importance as an inland trade route for timber and farming products, and Essex’s past as an import center for African ivory.