The Keene Electric Railway opened for regular service in September 1900. The first day was a free-fare holiday on which the public took full advantage of the opportunity to test the new trolley system. Passengers packed the cars, standing three-deep inside, while those who were unable to crowd into the vehicles watched from the sidewalks. Dirt and gravel from the recent construction lay deep upon the new rails and, as the wheels ground the stones, sparks flew in all directions.
Open trolley cars during the warm weather and enclosed ones in the winter became brief fixtures in Keene. Band concerts held in Marlborough were a means of attracting business to the railway, and special excursions on the line delighted all ages. Youngsters of the summer park programs had an outing each season at the Wilson Pond recreation area (called the "Rec"), climaxed by a ride on the electric cars back through the Square to Wheelock Park, to Marlborough, and return. A motorman of one of the first electric railway cars, Clarence L. Wyman, became general superintendent of the road in 1909. In 1926 the road petitioned to substitute buses for the trolleys. This petition was granted and the first of the motor buses ran on June 29 of that year. The last trolley operated over the July 4th holiday; the next morning the buses took over full operation. In 1929 the Keene Electric Railway was succeeded by the Cheshire Transportation Co., organized by Clarence L. Wyman and Louis N. Harper.