Chapel Street, An Original State Toll Road

May 15, 2020

Today when you stand on the corner of York and Chapel Streets you are at the heart of a busy downtown intersection. Surrounded by the Yale University Art Gallery, Rudolph Hall, the Yale Repertory Theater, bookstores, delis and restaurants it doesn’t resemble an outer boundary of the city. But until the 1840s that’s exactly what it was.

The city limit ended at York Street and everything west of that intersection along Chapel Street was once owned and operated by the Derby Turnpike Company. After the American Revolution, turnpikes were the region’s first “highways.” They were an interconnected series of (mostly) improved overland toll roads that dependably linked towns and communities throughout the area. Nearly all were private stock companies that were chartered by the state. This means that these main roads were privately owned and operated. At the time, private companies were more nimble and could raise capital quicker than the state or local governments. Keep in mind that most of the government’s structures were brand new and in the process of figuring out exactly how they were going to operate immediately after the country had won its independence from Great Britain. As we are experiencing today bureaucratic governance was not an overnight creation and not very smooth at first in practice. These toll roads were simply the physical ties that strung together a new country.

The Derby Turnpike Company was chartered in 1798. The toll road ran 8 miles from York Street to the Derby Landing, located at the confluence of the Housatonic and Naugatuck Rivers. Derby was a growing port village at the time and a direct connection to New Haven was advantageous to both towns, along with the taverns and farms that operated in between. With $7,500 in capital the road was cleared and a toll house established on a berm just next to the Maltby Lakes. The road was 18 feet wide allowing for stagecoaches and wagons to pass with some degree of comfort. The term “turnpike” was actually literal. At the toll house there was a gate or pike, and once payment was collected the pike was turned open and people were allowed to pass.

Turnpike companies as well as canals were generally hard pressed to turn a large profit for shareholders. Upkeep and maintenance ate into the profits. Through the 1800s, New Haven continued to grow into a regional economic and cultural draw, which drew investments away from Derby and the turnpike, centralizing capital in New Haven. In the 1840s, the Derby Turnpike Company sold off their holdings within the New Haven city limits. Derby Avenue became West Chapel Street, and the neighborhoods surrounding the intersection of York and Chapel Streets quickly expanded in density.

Across Connecticut the private toll roads eventually became public access ways. These were the templates for our modern automobile routes and highways. The Derby Turnpike remained in operation until 1897, making it the longest running private highway in Connecticut. In the 1940s, Route 34 was constructed on the original route of the turnpike. Today this road is still used by thousands of people daily, who are unknowingly still following the path of one of the first prominent roadways in the United States.

Jason Bischoff-Wurstle
Director of Photo Archives, New Haven Museum