Commuting is nothing new to Nutmeggers. But to appreciate our current challenges in “getting there,” consider what it was like centuries ago.

As early as 1699 roads had been laid out on routes still used today. But where today those roads are now lined with trees, in the mid-1700’s those trees were gone as most of southern Fairfield county had been cleared to allow for farming.

Jim Cameron

In the 1770’s the maintenance of Country Road (now known as The Boston Post Road) was the responsibility of the locals. Every able-bodied man and beast could be drafted for two days each year to keep the roads in good shape. But traffic then consisted mostly of farm carts, horses and pedestrians.

At the end of the 18th century it was clear that Connecticut needed more roads and the state authorized more than a hundred privately-funded toll roads to be built. Yes, friends… toll roads are part of our DNA.

The deal was that, after building the road and charging tolls, once investors had recouped their costs plus 12% annual interest, the roads were revert to state control. Of the 121 toll-road franchises authorized by the legislature, not one met that goal.

One of the first such toll roads was the original Connecticut Turnpike, now Route 1, the Boston Post Road. Another was the Norwalk to Danbury ‘pike, now Route 7.

On the Post Road four toll gates were erected: Greenwich, Stamford, the Saugatuck River Bridge and Fairfield. No tolls were collected for those going to church, militia muster or farmers going to the mills. Everyone else paid 15 cents at each toll barrier, about $4 in today’s money!

The locals quickly found roads to bypass the tolls which were nicknamed “shun-pikes.” Sound familiar?

Regular horse-drawn coaches carried passengers from Boston to New York. And three days a week there was a coach from coastal towns to Stamford, connecting to a steamboat to New York.

The last tolls were collected in 1854, shortly after the New York & New Haven Railroad started service. An early timetable showed three trains a day from Stamford to New York City, each averaging two hours and ten minutes. Today Metro-North makes the run in just under an hour.

The one-way fare was 70 cents vs. today’s $15.25 at rush hour.

In the 1890’s the one-track railroad was replaced with four tracks, above grade, thereby eliminating street crossings.

In the 1890’s the trolleys arrived. The Stamford Street Railroad ran up the Post Road connecting with the Norwalk Tramway; the latter also offered open-air excursion cars to the Roton Point amusement park in the summer.

Riders could catch a trolley every 40 minutes for a nickel a ride. There were so many trolley lines in the state that it was said you could go all the way from New York to Boston, connecting from line to line, for just five cents apiece.

The trolleys were replaced by buses in 1933.

Fast forward to the present where we are still debating tolls on our roads, possible trolley service in Stamford and T.O.D. (“transit oriented development”) is all the rage. Have things really changed that much over 200 years?

Posted with permission of Hearst CT Media. Jim Cameron is founder of The Commuter Action Group, and a member of the Darien Representative Town Meeting.

Jim Cameron is founder of the Commuter Action Group and advocates for Connecticut rail riders. He writes a weekly column called "Talking Transportation" for CT Mirror and other publications in the state. Read past Talking Transportation columns here. Contact Jim at

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    1. Nobody WANTS tolls, but most of us who want well-maintained, functional roads and bridges accept the necessity of actually paying for them. Tolls are user fees, and the added benefit is that we could collect substantial sums from out-of-state free loaders, reducing our own burden. Otherwise we’ll have to borrow even more money, driving down our credit rating and vastly increasing the debt we’ll pass on to our children. There is no free lunch.

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