This path follows the roadbed of the Savannah & Statesboro Railway (S&S RY), completed in 1899. It was created through the interests of timbermen and turpentiners and through the dreams of Statesboro citizens of becoming a railway center. The local depot stood near the corner of E. Vine and Railroad Streets. The company's secretary, J.A. Brannen, had an office at the Jaeckel Hotel. For 34 years, the S&S RY enabled residents to visit Savannah or take excursions to Tybee.
It also linked the county's farmers and merchants to railways serving the nation. Sites near depots, such as Brooklet and Stilson, became towns.
J.R. Anderson purchased the S&S RY in 1905. The Savannah & Statesboro RY operated at a profit for years and by 1910 owned 3 locomotives, 3 passenger cars, 2 baggage cars and 25 freight cars. In 1908, 4 trains ran daily between Cuyler and Statesboro with connections at Cuyler to Savannah. In 1911, the S&S RY bought the Savannah, Augusta & Northern Railway that operated 39 miles of track from Statesboro to Stevens Crossing. The company had planned to extend the rail line to Atlanta, but went out of business in 1933.