One source says the Trolley Company which in this case would be the Berkshire Street Railway built two Amusement Parks. One in Pittsfield and one in Great Barrington. OK-- the one in Pittsfield was Berkshire Park (although actually in Lanesboro)...Pontoosuc Lake Park in Pittsfield was also a Trolley Park but it seems to not get mentioned as under the Berkshire Street Railway ownership. The Pittsfield Electric Street Railway did not go to Great Barrington but the Berkshire Street Railway did. In 1910 the Pittsfield Electric Railway although it seems still profitable was ordered by the courts to fix various section of line due to 'safety' conditions. They did not and the courts gave ownership to New England Investment and Securities Company which ironic was owned by the New York, New Haven, and Hartford Railroad. The 'New Haven Railroad' owned the Berkshire Street Railway so ?? Getting confused ? Pontoosuc Lake Park might have survived post 1910 but unknown. Pontoosuc Lake was the major local resort but personally I have not seen it listed in trolley records as owned by the Berkshire Street Railway.
Great Barrington ?? If an Amusement Park was there as a trolley park I would guess the Great Barrington Fairgrounds. There was a 'golf grounds' a 'short stop' later. There are odds there might have been a 'fixed' Amusement Park there in older days. There were baseball and football games. In 1903 trolley schedule it shows half hour service between the Fair Grounds and Pittsfield during the summer. I only raise a mild question when I read the Berkshire Street Railway owned a park in Great Barrington when I never saw it in trolley records. (but in a modern publication)
Otherwise FINE. MANY MANY Fairgrounds had more than just an annual event and I try to stay away from listing them --- Annual Fairs/Carnivals.
Gotta admit with all the trolley stops 365 days a year something must have been there.
The Great Barrington Fairground was a major stop on the Berkshire Street Railway.