Bear Mountain


For the sure of foot and sound of wind, trek on a rugged forest path and scramble up steep ledges to the 2316 ft. summit of Bear Mountain, the highest mountain peak entirely within the bounds of Connecticut. Reaching the crest of this windswept mountain will inspire a feeling of accomplishment, and reward you with magnificent views of three states.


At the junction of Rte. 44 and Rte. 41 in the center of Salisbury, follow Rte. 41 north for 3.2 miles to the hiker parking area on the left. The entrance to Undermountain Trail is just beyond the parking area.

Walking Time: 5 to 6 hours

Level: Challenging

Distance: 6.7 miles


To reach the summit of Bear Mountain, you will follow the blue blazed Undermountain Trail and the blue blazed Paradise Lane Trail to the white blazed Appalachian Trail. To descend, follow the white blazed Appalachian Trail to the blue blazed Undermountain Trail to the parking area where this loop began. All white and blue double blazes in Connecticut are off set in the direction of travel with the top blaze. The entrance to the Undermountain Trail is just beyond the hiker parking area on Rte. 41. Keep to the trail's defined footway; travel in groups of ten or fewer, and carry out what you carry in.


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.

At the well signed intersection of Undermountain Trail and Paradise Lane (both have blue blazes), take a right onto Paradise Lane to continue your ascent up the mountain on a narrow forest path that evens out as you reach a high plateau.

Along the way, you will pass a beautiful Black Spruce Bog, a small pond and a swampy area peppered with colorful examples of rare flora and fauna. Look for mature American Chestnut tree's, some with diameters that exceed 8 feet. Hiking in late fall or winter, reveals views of the steep north side of Bear Mountain, on the left. As you traverse an open ledge, edged with mountain laurel and blueberry bushes, you cross the unmarked border between Massachusetts and Connecticut.

Soon you will come to a lovely grove of hemlocks located high above the steep south bank of Sages Ravine, well-known for its unspoiled natural beauty.

Following the blue blazes the trail begins to descend for 1/3 of a mile to the intersection of Paradise Lane and the Appalachian Trail, easily identified by its' white blazes.

Turn left onto the Appalachian Trail (don't turn right on the unmarked trail which leads to private property) and continue following the white blazes to the most challenging part of this hike.

Here, you will have to traverse steep slopes of ledge that go straight up for almost 1/4 of a mile. As you begin to climb look for natural hand and toe holds to help you scramble up Bear Mountain's steep rock face for the final 1/3 of a mile (500 vertical feet). As you ascend the face of Bear Mountain, look to the north, over your shoulder, for expansive views of Connecticut's beautiful Litchfield Hills and beyond.

Perched on the summit of Bear Mountain, is a monument commissioned by Robbins Battell of Norfolk in 1885, and built by a Salisbury stone mason to proclaim this spot as the highest point in Connecticut. It is said that Robbins Battell could see this monument, from his living room at the Whitehouse in Norfolk. Today the Whitehouse is the site of the Norfolk Music Festival and Yale Summer School of Music and Art. Since the advent of World War II, it has been determined that the state's highest point is on a shoulder of Mount Frissel, whose summit is in Massachusetts.

This exhilarating trek rewards those that reach this windswept mountain top with a panorama that is breathtaking. The summit is surrounded by picture perfect peaks, rolling hills and glistening lakes. To the west is Mount Frissell, Round Mountain, Brace Mountain and the Catskills, to the east is Salisbury's Twin Lakes and Canaan Mountain. The southeast reveals stupendous views of Mohawk Mountain in Cornwall and Haystack Mountain in Norfolk. The north offers views of Mount Everett (the mountain with the tower), Race Mountain and Mount Greylock.

Begin your descent by following the white blazes. In ten minutes you will reach another splendid view to the south & west. A rock to the right of the trail provides a perfect vantage point to look down on Riga plateau and beyond to a stunning view of Mount Gridley, Brace, Mountain and Round Mountain.

Following the white blazes, your descent continues on a rocky path that can be tricky in inclement weather. When you reach an old woods road, turn left onto the road and continue following the white blazed Appalachian Trail.

Soon you will reach a T junction, known as the "Riga Junction", where the Appalachian and the Undermountain Trails meet. Take a left onto the blue blazed Under Mountain Trail and follow its steep descent through a mixed hardwood and conifer forest for 1.9 miles to the hiker parking lot where this loop began.


It is always safer to hike in the mountains with a companion. It is advised that you bring along the following items: fresh water, a picnic lunch, a small flashlight, a compass, and a camera.