This 1768 Bill of Lading stipulates the details of an agreement between prominent Windsor shipbuilder and merchant Ebenezer Grant (1706-1797) and shipping agent Joseph Forbes to transport Grant’s cargo aboard the ship Hartford bound for Barbados. WHS collections 2003.28.1

The word Connecticut translates roughly to “long river” in Algonquian, but despite its great length, few portions of the river drop to a significant depth. The first European vessel to travel along its banks was the makeshift Dutch yacht Onrust, captained by Dutch explorer Adriaen Block. The Onrust was a shallow-keeled ship, which allowed it to successfully navigate the treacherous sandbar at the mouth of the river, as well as its shallows that are little more than several feet deep in various locations.

In the decades following the river’s discovery, as various settlements grew in Connecticut, New York, and Massachusetts, the numerous shallows and oxbow bends of the Connecticut continued to limit the river’s potential as a trading hub. However communities along the river built relatively small, slow, and clunky ships with low decks and high waists, nicknamed “Horse Jockeys” that allowed them to successfully navigate both the open ocean and upriver as far north as the impassible Enfield Rapids.

Throughout the 17th, 18th, and early 19th centuries, maritime trade along the Connecticut River slowly and steadily grew, yet the state remained a backwater in comparison to both Massachusetts and New York. Exports consisted mainly of raw resources such as lumber, grains, and meat, while imports consisted of luxuries such as European goods, sugar, and rum. The most lucrative trade destinations for ships from the Connecticut valley were the British-owned islands of the Caribbean. Amazingly it would often take these ships just as long to travel up and down the Connecticut River as it would to travel from the shoreline all the way to the Caribbean. Crews would often be forced to sink an anchor upriver or tie a line to a tree at a bend and literally pull the ship along in order to make headway.

The Connecticut River’s depth shrinks to impassability a little north of this view, which shows Palisado Avenue, Macktown Road, and Hayden Station Road running alongside the river. WHS collections 2003.41.65, photo by Philip F. Ellsworth.

While trading upriver was certainly arduous, there were certain silver linings to Connecticut’s situation. Merchants faced smaller startup costs here, and as the British increasingly tightened mercantile trade restrictions throughout the 1700s, they often overlooked the smaller Connecticut ports in favor of Boston and New York. These qualities helped the towns along the Connecticut River collectively develop into the most significant shipbuilding and trading hub between New York and Boston by the time of the American Revolution.

Windsor Historical Society interprets and gives tours of two historic houses, the Strong- Howard House and the Hezekiah Chaffee House, and both the Howard and Chaffee families had strong connections to maritime trade. Captain Nathaniel Howard was one of the ship captains who mostly transported goods between the Caribbean islands and Connecticut. Across the street John Chaffee partnered with merchants and Palisado Green neighbors Horace and James Hooker to form Hooker and Chaffee, a maritime trading company which operated successfully from the 1790s to 1804.

When thinking of the serene New England towns and villages that line most of the Connecticut River today, it is difficult to imagine that at one time trade ships carrying goods from the Caribbean and Europe traveled its waters. While the natural limitations of the Connecticut River hampered the growth of trade, it is important to remember that the early economies of communities such as Windsor depended on shipping and trade along the river.


by John Mooney, education and outreach manager, 2017