Bear Mountain is an absolutely beautiful hike. It’s about 6.7 miles long and crosses into the Appalachian Trail for a small section. The summit is 2,323 feet high and offers stunning views of the surrounding area. A cool bonus about hiking Bear Mountain: it’s the tallest mountain summit in Connecticut! However, it’s not the state’s highest point—that honor belongs to a spot on Mount Frissell, whose actual summit is located in Massachusetts.
At the summit of Bear Mountain, you’ll find the remains of a stone building built in 1885. Standing about 8 feet high, these remnants look more like a giant cairn than a structure, but they’re still pretty fascinating. On clear days, you can enjoy views of nearby peaks: Mount Race and Mount Everett to the north in Massachusetts, Mount Frissell to the west, and Mount Gridley to the southwest. Along the trail, keep an eye out for blueberries during the season!
Bear Mountain in Connecticut offers a delightful and challenging hike for both humans and their furry companions. Starting from Route 41, the Undermountain Trail is a popular starting point. At the split, many hikers enjoy taking the Paradise Lane Trail, which provides a gentler route with plenty of watering spots to keep your pup hydrated and happy.
As you continue, you’ll join the famous Appalachian Trail (A.T.). Turning left will lead you toward the summit, but be prepared—this section becomes steeper with rocky inclines and switchbacks. While these parts can be fun and adventurous, they may require some extra caution. A steady, gentle pace is recommended for your pup.
For those seeking a less rigorous option, the Undermountain Trail offers an alternative. At the Riga Junction, marked by a prominent sign, take a right onto the A.T. for a less steep approach to the summit. Most dogs find this route more accommodating, and it’s a great way to ensure your furry friend has an enjoyable hike.
After reaching the summit and soaking in the views, you can retrace your steps for a comfortable return trip.
The hike begins at the Undermountain Trailhead, located on Route 41 in Salisbury, CT. Parking is available at the trailhead, but it can fill up quickly on weekends and during peak hiking seasons, so arriving early is a good idea. The trailhead doesn’t have restrooms or water fountains, so plan accordingly before you arrive.