People complain about Connecticut’s roads. I get it. The potholes. The detours. The construction that begins in April and somehow ends in April of the following year. But before you curse your GPS, consider this: getting anywhere in colonial Connecticut could be genuinely life-threatening.
We’re talking about a time when “road conditions” meant snakes, waist-deep mud, fording unbridged rivers, and a footpath barely wide enough for a horse. And yet, Connecticut built America’s first great transportation network. It started with the King’s Highway.
In 1672, New York Governor Francis Lovelace had a problem: getting a letter from New York to Boston took forever and often arrived mangled, late, or not at all. Sound familiar? His solution was a monthly postal route, and in January of 1673, the first rider began to blaze what would eventually become the Boston Post Road, US Route 1.
Here in Connecticut, that route followed an ancient Pequot trail, a path Native Americans had kept clear for centuries, it’s said, by burning back the brush each November. So we didn’t build the road. We inherited it. And then we paved over the history with good intentions and, for a while, added toll booths.
In 1792, Connecticut solved the pesky problem of “who pays for roads” the way it still does: user fees. The Mohegan Turnpike was the state’s first, and the country’s second, turnpike: proof that Connecticut has always been eager to be an early adopter of charging people money to get somewhere. Over the next four decades, roughly 100 private turnpike companies laid some 1,400 miles of toll roads across the state. Most of those concerns eventually went bankrupt.
By the early 1700s, Connecticut had three branches of the Post Road threading through the colony: the Upper route through Hartford and Springfield, the Lower route hugging the Sound through Stratford and Saybrook, and a Middle route cutting diagonally through Bolton and Woodstock. The road system was, for its time, impressive. Travel was still agonizing… a trip from Hartford to Boston could eat up several days.
It’s said that in 1753, Benjamin Franklin himself drove the Lower Post Road in a carriage fitted with an odometer, standardizing postal rates by distance and ordering stone mile-markers placed along the route. Connecticut’s General Assembly then required every town to erect them. Imagine that: State Government mandating infrastructure improvements while arguing about who pays for it. Some things never change.
But the real transportation superhighway of colonial Connecticut wasn’t a road at all. It was the water.
Long Island Sound was our I-95, only it actually worked. New London, blessed with deep water and a protected harbor, was one of the colony’s busiest ports. In a single year, 1748 to 1749, 62 vessels departed for foreign ports. Norwich and Middletown, reached by river, funneled the colony’s farms and forests down to waiting ships. New Haven moved goods both north and south.
And what were they shipping? Horses, cattle, lumber, salted beef, and barrel staves, all headed to sugar plantations in the West Indies. What came back in exchange? Molasses, rum, coffee and, shamefully, enslaved human beings. The slave trade made Connecticut both prosperous and complicit in equal measure.
Much of this water commerce ended, suddenly and violently, in September 1781, when Benedict Arnold sailed into New London harbor and burned it to the ground. The King’s Highway survived. The waterfront never fully recovered.
So, next time you’re stuck on I-95 wondering why our state can’t seem to get transportation right, remember: we’ve only been at this for 350 years. And we’ve always moved, but never moved quite fast enough.
