At the edge of the driveway to the Bennington Museum
When wealthy North Bennington resident Trenor Park purchased the Bennington-Rutland Railroad, he found that the railroad "barons" of the Troy and Boston Railroad refused him access to the New York lines. Rather than fight this monopoly, Park built a rail line from Bennington to Lebanon Spring, NY, where he could transfer his trains to southbound rails while bypassing Troy. The dozens of turns over 40 miles of hilly terrain gave this stretch of railroad the name "Corkscrew." Passenger service was canceled in 1931 and the line was officially abandoned in 1953. Remnants of the old rail bed can be seen where it crossed the highway at this point.
Railroads (Stephentown Genealogy.com)
Corkscrew Recreational Path Feasibility Study