As runners pass the first mile mark, they begin to leave the town of Litchfield behind and enter the bucolic landscapes of ponds and forests that are characteristic of the race. It is easy to be lulled into thinking that the landscape always appeared this way. This mindset, however, will cause the runner to miss a significant piece of the town’s history.

The entrance to the Litchfield Greenway on South Lake Street, once the route of the Shepaug Valley Railroad.

Reaching the bottom of Gallows Hill, the runner briefly turns on to South Lake Street. Here, the Shepaug Valley Railroad (later the Shepaug, Litchfield and Northern Railroad) crossed the road as it neared the end of its line at the Litchfield Station on Russell Street. A little over a mile of the railway’s path is preserved as the Litchfield greenway.

A receipt for stock in the Shepaug Valley Railroad purchased in 1870 by Captain George Colvocoresses of Litchfield. Courtesy of Litchfield Historical Society.

The construction of the railroad was both celebrated and feared by the residents of Litchfield. When Edwin McNeil surveyed the line in the 1860s, he was met with threats by armed farmers. Construction began in 1870, with one crew beginning work in Litchfield and another in the Hawleyville section of Newtown. By January 1872, regular rail service was running to Litchfield. What passengers most noted about the journey was how winding it was; in one stretch, 32 miles of track with between 150 and 200 curves were needed to cover what the crow could travel in 17 miles.

On this map of Connecticut railroads, the Shepaug Valley is depicted as a thin line between Hawleyville and Litchfield, indicating its relative traffic compared to the Housatonic to the west of the Central New England to the North.

Still, the railroad did provide greater access to the outside world for Litchfield residents. A passenger train that left Litchfield at 6:25 a.m. reached Hawleyville at 8:00 a.m., where a connecting train reached New York City’s Grand Central Station at 10:33 a.m. The line also transported iron, granite, manufactured goods, and ice from the county’s ice houses. The line went bankrupt twice in its first fifteen years, merged with the New York, New Haven and Hartford in 1898 (all the state’s railroads were eventually part of this line, known as “the Consolidated”), and ceased operations in 1948.

The Litchfield train station, on Russell Street. 

Runners will again encounter the remnants of the Shepaug Valley Railroad when they exit the Plumb Hill fields and turn right on to Whites Woods Road. Here the railroad crossed from one side of the road to the other. And when runners turn from Bissell Road on to Whitehall Road and enter the White Memorial Foundation, they will be very near the point where the SVR turned from running parallel to Route 202 and headed toward its termination at Russell Street.

For more information on the history of the Litchfield Road Race, see Lou Pellegrino’s forthcoming book A History of the Litchfield Hills Road Race: In Smallness there is Beauty. (Available May 2016)