If you stood here in the late 1700s looking east toward the Connecticut River a forest of ship masts would bob before your eyes. On docks lining the riverside, sailors and merchants bustled back and forth to tall ships which had just arrived in port, or would soon set sail. Ferry Boats
From Middletown's earliest days, the river had shaped the town's character and development. By the 1660s, shipyards here were busily building vessels. Soon Middletown merchants developed a thriving trade with ports along the East Coast, in the West Indies, and even in Europe. By the late 18th century, the maritime trade had made this Connecticut's most populous city. Thousands of local men and boys became sailors, many of whom never returned to Middletown, dying in shipwrecks or from tropical fevers.
Steamboats plied the river as early as 1815. In 1822 a Middletown man named 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, encouraging local manufacturers who could now ship their goods all over the World.
The first bridge spanning the Connecticut River at Middletown was the Air Line Railroad's swing bridge that opened in 1872 and still stands today. In 1896 a drawbridge linked Middletown
and Portland; today the graceful suspension bridge of 1938, the Arrigoni Bridge crosses the river at about the same place.
Middletown's connection to the river began to wane in the 20th century especially after the construction of Route 9, which separated the downtown from the river that once gave it its character. But the river still draws people down to its banks-now a restful public park-and each autumn brings thousands of spectators to watch college crew teams race in the Head of the Connecticut Regatta.
Families began settling across the river in East Middletown (now Portland) before 1700. In 1726, a small ferry provided regular crossings. As the community there flourished, rowboats and canoes no longer answered its needs; by 1830 a large flat-bottom ferry carried the growing numbers of passengers, along with livestock, carts and carriages. In the 1850s, steam-powered ferryboats took over. Until the first passenger bridge opened here in 1896, ferries remained indispensable, crossing the river approximately where the Arrigoni Bridge stands now.
For decades, the steamboats travelling between Hartford and New York stopped in Middletown, docking at the foot of College Street. Raymond Baldwin, who grew up here in the 1890s (and later became Governor of Connecticut) recalled the evening ritual of "the arrival and departure of the New York boat... That was announced by the long blast on the whistle to open the highway bridge and the railroad bridge. Then another long blast as the steamer approached the dock. There was a clanging of bells, a churning of water and throwing of the heavy lines and the hauling of the ship into the dock and the running out of the gangplank. Then these fellows, the 'roustabouts' with hand trucks... they'd take aboard the steamer heavy hardware from Wilcox and Crittenden's, the big crates from the Russell Manufacturing Co. and boxes from the Starr Mill and other manufacturing concerns around the town. The big freight house would be emptied in the course of ten or fifteen minutes. Then the old steamer Middletown or Hartford, whichever it happened to be, would blow a whistle and cast off the lines. There would be more ringing of bells and the churning of water and she'd start down the river, a majestic sight."