Follow the dirt path from the parking area to a bulletin board that posts the most recent trail information. Brochures provided by the Connecticut Chapter of the Appalachian Mountain Club detailing parking, camping and routing information can be picked up here.
To begin your hike to the summit of Bear Mountain, head into the woods on the blue-blazed Undermountain Trail, one of the most popular access trails to the Appalachian Trail in the state. Walking along a narrow woodland path, you will notice that it begins to ascend gradually, gently at first, but soon turns into a steady, upward climb. As the trail widens it becomes apparent that this was once an old woods road that was used to haul charcoal made in these hills to Salisbury's iron ore blast furnaces. The trail continues to ascend for 1.1 miles through a mixed hardwood and pine forest to Paradise Lane.