Skyline Trail Distillery

The Skyline Trail offers scenic vistas and access to some of the premier tourist attractions of the Pioneer Valley. However, many are surprised to learn of its secretive past as the main transportation route for many of the era’s early bootleggers.

The landscape of the surrounding rolling mountain forest is dotted by long-forgotten stills that once served as the main distillation spots for some of the finest moonshine of the time.

The Skyline Trail was then used to transport the bottled goods to the Chester train yard, where railcars would be loaded in the dead of night to supply the bustling speakeasies of Albany and Boston at their final destinations.

The cool, crystal-clear waters of Day Brook and Still Brook provided a smooth base that made this group of rag-tag bootlegger's product the most sought-after liquor of the time.

Eventually, the notoriety brought too much attention to the operation and it came to a violent, grinding halt. So ended the "prohibition trail" and a smooth, soul-warming alcohol that generations haven't been able to experience for themselves, until today.

Deep in the heart of Chester, off the beaten path of the paved modern Skyline Trail, down an old dirt road and hidden in a shadowy shoulder of the hill forest is one abandoned still that has been discovered and is being restored back to its former glory.