From Middletown's earliest days, the Connecticut River shaped the town's character and development. By the 1660s, shipyards here were busily building vessels, and Middletown merchants soon developed a thriving trade with ports along the East Coast, in the West Indies, and in Europe. By the late 18th century, maritime trade had made it Connecticut's most populous city, while thousands of local men and boys became sailors, many dying in shipwrecks or from tropical fevers. Steamboats plied the river as early as 1815, and in 1822 William C. Redfield piloted his side-wheel steamer between Hartford and New York, stopping here on the way. For over a century, steamboats carried passengers and freight in and out of Middletown, supporting local manufacturers whose goods could be shipped widely. Families began settling across the river in East Middletown, now Portland, before 1700, and ferries provided regular crossings from 1726 until bridges gradually replaced them. The Air Line Railroad's swing bridge opened in 1872, a drawbridge linked Middletown and Portland in 1896, and the Arrigoni Bridge of 1938 now crosses at about the same place. Middletown's connection to the river waned in the 20th century, especially after Route 9 separated downtown from the river, but the river still draws people to its banks and each autumn brings thousands to watch the Head of the Connecticut Regatta.