About Guided Hike to Hurlburt's Hill

Trace the footsteps of history on this guided hike from the historic Ashley House in Sheffield, MA to the summit of Hurlburt’s Hill at Bartholomew’s Cobble. Begin your journey where Elizabeth Freeman’s courageous fight for freedom began, and follow scenic woodland trails through the heart of the Housatonic landscape. Along the way, your guide will share stories of the land’s natural and cultural history—from colonial-era legacies to the ecological richness of the Cobble. The hike concludes at the breathtaking meadow summit of Hurlburt’s Hill, offering panoramic views across the Berkshires and into Connecticut.

This tour will meet outside the Ashley House. While it is free, pre-registration is required.

Distance: ~3.5 miles round-trip
Difficulty: Moderate; includes some steady uphill walking
What to Bring: Water, sturdy shoes, bug spray, mosquito net if you have one

Join us earlier in the day for our Elizabeth Freeman Day Celebration!

Register