Over 90 years have passed since the last electric trolley car rumbled on rails from Pittsfield to Great Barrington. At its peak in 1917, the local trolley company—known as the Berkshire Street Railway—was one of the largest in the United States. It operated 170 miles of track that extended from Canaan, Conn. through Berkshire County, and into the neighboring states of Vermont and New York.
Although the trolley ran right down the middle of Main Street in most towns, Stockbridge was an exception. Many Stockbridge residents were strongly opposed to the laying of tracks through the village center. After months of controversy, track construction was “detoured” at the South Lee and Stockbridge town line. There, the line crossed the Housatonic River, and then ran parallel to the New Haven Railroad tracks. The trolley again crossed the river next to the old Ice Glen bridge as shown in the early 1900s postcard view above. It then followed what is now Park Street to the trolley stand shown below, circa 1909. This building still stands at the entrance to the Stockbridge skateboard park, and is used by the town for storage. As the automobile became more popular, travel by electric rail declined. The final trolley passed through Stockbridge on January 28, 1930.
