What we know today as the State of Connecticut is actually comprised of three colonies, Connecticut, New Haven, and Saybrook, which merged in the 17th century. One of the reasons New Haven and Saybrook didn’t make it as independent colonies was the failure of larger towns to develop at their locations, in spite of sitting where rivers intersected with Long Island Sound.
Founded in the mid-to-late 1630s, New Haven and Saybrook had very little time prior to the English Civil War to attract new immigrants. Other than an odd brand of extreme Puritanism in New Haven, they didn’t offer enough to entice enough Puritans out of Massachusetts. Saybrook Colony quickly merged with Connecticut, which was establishing itself as a kinder, gentler Puritan colony built around farming, not fishing, and one that even let Anglicans (Episcopalians) vote. This was unacceptable to the Puritans of New Haven Colony, some of whom left and established Newark, New Jersey when the English forced New Haven to merge with Connecticut in the 1660s. The New Haven Colony didn’t just include what is now the City of New Haven, but much of the surrounding county, and the coastline as far as Greenwich. This was one factor that led to Connecticut developing a “panhandle” near its border with Westchester County.
But within New England, this ultimately created an unusual situation where the insignificant Charles River produced a major city at Boston, and the best the mighty Connecticut River could come up with was Hartford, which was 40 miles inland. Moreover, the largest Connecticut city in 1800 was not New Haven, Hartford, or future-Investment-Banking-outpost Stamford. Rather, it was New London. New London had a far less impressive river than Old Saybrook, but it became a far more important center of business activity in the early 19th century.
Something was clearly going on in Connecticut that meant its extensive coastline could only produce mediocre ports. Never mind Boston — by the 1790 census, and long after the Puritan Paradise years, the Massachusetts towns of Salem, Marblehead, Gloucester, Newburyport, and Nantucket were all larger than any place you could find in Connecticut.
The lack of major cities in Connecticut had nothing to do with the size of the state itself. After the Revolutionary War ended, it had four times as many people as Rhode Island, but not a single city as large as Newport or Providence.
A major problem for Connecticut’s urban growth was Long Island. The Sound in between them pulls in freshwater, and ends at the East River in New York City. Now imagine you’re a whale — is this is a spot you’ll swim towards?
We talk a lot about cities needing to attract people, but what about animals? The towns developing along the Southeast coast of New England needed to attract whales, because their economies were as centered on a single industry as Detroit was in the 1920s. New Bedford, Nantucket, Newport, and New London might as well have been Whale OPEC. Whale oil, and the even fancier Sperm oil were the original fuel of America, used for lamps and candles.
New London, located near the eastern edge of Connecticut and its largest town in 1800, didn’t have as bad a “Long Island” problem the rest of the state did. Today the salinity of the Sound there is not much lower than the 35 parts per thousand found in the Atlantic, while around New Haven and west salinity drops by 40%. This is a big problem when you’re trying to build an economy around saltwater sea life.
The lack of whales willing to swim towards the Bronx wasn’t the only issue plaguing the growth of Connecticut towns. Many of the successful ports elsewhere in New England, were north of Boston, and not part of the whaling industry further south. But as time went on, they too depended on a single industry to distinguish themselves from Boston, and that industry was lumber. It was no coincidence that Portland, Oregon was named after Portland, Maine; both got their start selling and shipping trees. Yet here again, Connecticut towns were at a disadvantage, too far away from the deep woods of Northern New England.
Given the importance of saltwater sea life to colonial New England’s urban development, Long Island played a major role in slowing Connecticut’s urban growth. And unlike their peers in Massachusetts and Rhode Island, no Connecticut city has ever been among the country’s ten largest.