The Greylock Recovery: Therapy in Boots Hike is a full-day, community-based hiking event designed to support and celebrate recovery through nature, movement, and connection. We’ll be hiking up Mt. Greylock—the highest peak in Massachusetts—via the scenic and accessible Cheshire Harbor Trail.
No distractions. No buzz of phones. Just the sound of the wind through the trees, birds, and your own thoughts. It’s grounding. It’s a day to help you slow down and reconnect with yourself. Plus, sharing the experience with others on a similar path—laughing, struggling, encouraging each other—builds bonds. You’re not doing it alone. You never have to.
This event is open to anyone in the recovery community, those supporting loved ones in recovery, and allies looking to engage in a meaningful day of reflection, growth, and camaraderie in nature.
Time: 9:00 AM Start
Location: Cheshire Harbor Trailhead – West Mountain Rd, Adams, MA
Trail: Cheshire Harbor Trail (out-and-back)
Length: 6.4 miles (round trip)
Elevation Gain: 1,922 feet
Estimated Total Time: ~3 hours 51 minutes
Difficulty: Moderate – appropriate for beginner to intermediate hikers with basic fitness
8:30 AM: Arrival, check-in, light stretching/warm-up
9:00 AM: Hike begins
Midday: Arrival at summit and recovery circle/reflection time
Summit Celebration: We are planning to have a food truck (Chef Chris Bonnivier) at the top to provide a nourishing and celebratory meal after the hike
Afterward: Group photo, informal hangout, optional journaling/personal reflection time before descent
Wear comfortable, weather-appropriate hiking clothes and sturdy shoes
Bring a reusable water bottle, sun protection, and any personal snacks or medications needed