Beartown State Forest Ridge Road

Beartown State Forest’s Ridge Road system climbs through 12,000 acres of pristine Berkshire wilderness, following old logging roads that access some of Massachusetts’ most remote backcountry camping. The main route parallels Benedict Pond before ascending to Sky Peak via a series of technical switchbacks carved into steep mountainsides during the 1930s CCC era. The infamous “Rock Garden” section near the AT crossing tests approach angles and articulation as you navigate house-sized boulders and exposed ledge — locals call it the toughest technical section in western Mass.

This is expert-level terrain requiring serious 4WD capability, rock sliders, and preferably a spotter for the technical sections. Spring runoff creates dangerous washouts, and winter access is snowmobile-only. The payoff includes legal dispersed camping at high elevation with no permits required, plus direct access to Appalachian Trail shelters. Carry extra fuel and water — the nearest services are 45 minutes down the mountain, and cell service is nonexistent once you’re committed to the ridge route.