During the 1700s, Middletown entered a golden era driven primarily by maritime trade, becoming by 1750 the most populous and one of the richest towns in Connecticut. At its riverside docks, sea captains loaded ships with wheat, beef, pork, cheese, corn, horses, pigs, and lumber for ports such as Boston, New York, Philadelphia, and the West Indies, returning with sugar, coffee, rum, spices, and imported European goods that brought substantial profit. Merchants and captains sometimes made fortunes, but the sea was dangerous and unpredictable, and storms could destroy cargoes, sink ships, kill crews, and leave some vessels lost forever. Much of the town's livelihood was tied to the sea, as shipbuilders constructed hundreds of vessels, sailmakers stayed busy, bakers prepared ship's bread, and Philip Mortimer operated a ropeworks in the North End. Middletown's success drew merchants from distant places, even as its area was reduced by roughly half in 1769 when residents east of the Connecticut River formed the separate town of Chatham, including present-day Portland and East Hampton. When the American Revolution began in 1775, Middletown strongly supported the colonies by supplying the army with goods from guns to beef to mittens, while hundreds of local men served in the Continental Army or state militia and others built and manned privateers authorized to capture British vessels. At least a dozen African Americans from Middletown served in the Revolution, either as free men or as enslaved men promised freedom for enlisting, and Black participation in the war helped pave the way for Connecticut's 1784 gradual emancipation law; by 1800, most of Middletown's African American residents were free. The Wangunks, whose way of life had already been under increasing threat, sold much of their ancestral land or left for Native settlements in New York State, and by 1800 only a handful remained in Middletown, some having married into local African American families. Religious freedom also expanded, with an Anglican parish formed in 1750, a Methodist society in 1791, and a Baptist church in 1795. By 1800, Middletown had become a bustling river port and one of Connecticut's first four incorporated cities, with wealthy merchants and sea captains in riverfront mansions and a prosperity that supported 22 grocery stores, 11 dry goods stores, two bookstores, two goldsmith shops, and three furniture makers.