The Griswold Inn

The Griswold Inn was founded in 1776, the same year the Oliver Cromwell, the first American Revolutionary warship, was built just down the street in Essex Harbor. Its famous Tap Room occupies Essex's first schoolhouse, built in 1738 and moved to the site by a team of oxen on rolling logs in 1801. British troops captured and used the inn during the War of 1812, and during Prohibition it operated as a speakeasy supplied by river rum runners; a copper still was discovered in the kitchen ceiling during a 1980s renovation. Only six families have owned the inn in 250 years, and it houses one of the largest privately owned maritime art collections in the country. It marked its 250th anniversary in 2026, having never closed through war, Depression, or Prohibition.

Every Monday night since 1972, the inn has hosted sea chantey singalongs led by the Jovial Crew, a tradition of more than half a century celebrated by Atlas Obscura.

What to order: House-made Hot Buttered Rum (the inn sells its own all-natural mix of grass-fed butter, brown sugar, molasses, and spices) served in the Historic Tap Room.