Remnants of a Bygone Era : Deep in the woods of the Steep Rock Preserve, sits one of the few remaining landmarks of what once was the Shepaug Railroad. The Shepaug Railroad was chartered in 1868 between Litchfield and Hawleyville, CT and began operations in 1871. The Line was renowned for its route, it was said that it took 32 miles of track to travel 18 miles. There were reportedly 192 curves between Litchfield and Hawleyville which works out to be about 6 curves per mile. In 1891 The Housatonic RR took over operations of the line and eventually the line would be leased and operated by the New Haven RR from 1898 to 1948. In 1949 the line was abandoned with all of the track and most of the major bridges removed. This 235ft curved tunnel is one of the last major landmarks left of the rail line. The only traffic this tunnel sees now is the many hikers, mountain bikers, and horseback riders that utilize the old ROW as a trail on the Steep Rock Preserve.
