Bear Mountain

This popular 5.2-mile out-and-back hike climbs approximately 1,555 feet to the summit of Bear Mountain, the highest mountain peak located entirely within Connecticut. The hike begins at the Undermountain Trailhead parking area on Route 41, north of Salisbury. The Undermountain Trail ascends steadily through a hardwood forest and crosses several small streams. After passing the intersection with the Paradise Lane Trail—which offers options for loop variations—the trail reaches the Riga Junction and intersects with the Appalachian Trail. Turning north onto the Appalachian Trail, the ascent becomes steep and rugged, requiring hikers to scramble over steep rock ledges. The 2,318-foot summit features a large, historic stone pyramid monument built in 1885. This vantage point offers panoramic views of the Taconic Range, the Berkshires, and the Twin Lakes.