The Long Trail is America's oldest long-distance hiking trail, running 438km along the spine of Vermont's Green Mountains from the Massachusetts border to the Canadian border. Near Killington, it shares its route with the Appalachian Trail for about 160km — the longest section where the two trails overlap. Sherburne Pass (Route 4) is a major access point for both trails, just 5km west of the Killington Access Road.
Day hikes from Sherburne Pass include the Deer Leap Mountain summit (excellent views with minimal effort) and the approach to Pico Peak. For longer walks, the trail shelter system along the Long Trail means it is possible to do multi-day sections with just a pack — the nearest shelter to Killington is the Churchill Scott shelter, about two hours north on the trail. In autumn, the hiking is spectacular but the trails are crowded; weekdays in September and October are much quieter than weekends.