Fall Foliage Runs in Massachusetts

North Main St., Lanesborough

Photo by Henry R. Dondi

There’s an incredible wealth of fall foliage routes in western Mass. and the Berkshires. This one’s a bit of the beaten track, courtesy of the folks at Berkshire Sports.

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 all their unspoiled glory.


  • 5 miles
  • 585 feet
  • Intersection of Greylock Road and North Main Street split
  • Parking in town