Back in the day, about 100 years back, this hill hosted the Winter Carnival. You wouldn’t know it now, but people came by the train load from as far as Boston & Worcester to take part. There were local hotels and inns for lodging, all gone now, some lost to fires.
It was a different time, no better, no worse than now. The hill still hosts sledding and has been set aside from development, but people’s tastes changed, train lines fell out of use and the carnival ceased to be. Cars allowed people to held to larger places to ski, and many of those places have ceased to operate as people have preferred ski resorts. It is the relentless march of time and trends.