My memories of growing up in Littleton during the 50/60's was so different as compared to today. The norm was to be outdoors. At the time television was just evolving with only 2-3 channels to watch, so there little reason to stay indoors. Parents would encourage their children to go outside, make friends and play. So we did. We played baseball, explored, swam, fished, built forts, went sledding or just hung out
The Clubhouse
Clubhouse hill is a very steep rise where at the very top "The Clubhouse" was once located almost adjacent to the water standpipe. The Clubhouse was owned and operated by the Long Lake Association and used for various Lake community events. At the time everyone knew about Clubhouse Hill and for all intents and purposes most thought that the road was its namesake. In fact it wasn't until about 15 years ago did I learn the true road name Emerson Drive.
During the mid to late 1950's I recall dances and even a boxing event held at the clubhouse. Historical records stated the clubhouse's large dance floor with comfortable wicker furniture allowed for dances with bands from Acton and the popular Farmer's Swing band from Littleton. Many romances between Littleton residents (townies) and folks from cities like Somerville and Arlington were kindled there.
Boyhood trials were achieved on this hill. Most boys were dared or challenged to ride a bike in the summer or a sled in the winter from the top of the hill. Someone would be on the lookout below watching for cars and giving the OK to go! Your first trip down was indeed quite scary and on bike one didn't stop until you reached Pops. Another fun memory is watching cars trying to climb the hill during a snowstorm; most cars failed and we would cheer and laugh.
The Clubhouse stopped functioning in the late 50's, then taken over by the town and razed in the mid 1960's. Today a private home sits on the old site.
Parking is limited at the trailhead. You are looking for a camo pill bottle that is winter friendly