Mt. Greylock from Lanesboro Wikimedia Commons

The team at Berkshire Sports are a wealth of information when it comes to athletics in Western Mass, and running routes are no exception. They recommend this hilly, but quiet and low traffic route through Lanesborough, starting where Greylock Road and North Main Street split. It’s mostly dirt, so the track is easy on the joints and super-scenic. Start by heading northwest on Scott Road for about half a mile before turning right on Kessler Road. This long stretch of road carries on for a secluded 4.5 miles, including one challenging hill, before it drops onto a multi-use path that connects with North Main Street. Take a right on North Main Street as it winds down a hill and back to the starting point (the last half mile or so is pavement). This lesser traveled route is a great way to experience the Berkshire woods in in all their unspoiled glory.

Essentials
  • 5.1 mile loop
  • 586 feet
  • Intersection of Greylock Road and North Main Street
  • Park on the island at the intersection