Bear Mountain (Connecticut) via Undermountain Trail Hiking Guide
Bear Mountain in Salisbury is the highest peak in Connecticut, though not the state's highest point: that sits on the south slope of Mount Frissell, whose summit is in Massachusetts. The usual climb follows the blue-blazed Undermountain Trail from Route 41 to the Appalachian Trail and then up a rocky finish to a stone monument on top. It sits in the state's far northwest corner and is the biggest day hike in this group.
The Climb in Numbers
Hiking Project maps the out-and-back at 5.4 miles with about 1,549 feet of climbing and rates it intermediate to difficult. A Lakeville Journal trail guide breaks the route into about 1.9 miles on the Undermountain Trail to Riga Junction and 0.9 miles on the Appalachian Trail to the top, which is a little longer, and suggests allowing about five hours round trip. Hiking Project's map tops out at 2,313 feet; the Lakeville Journal gives the summit as 2,316.
Route Description
The Undermountain Trail starts at a small lot on Route 41 in Salisbury. It climbs gradually and then more steeply through birch, oak and beech, crossing several small streams and footbridges, and passes the junction with the Paradise Lane Trail, which makes a longer loop possible. Wooden stairs lead up to Riga Junction, where you turn right onto the white-blazed Appalachian Trail. The last 0.9 miles is the hardest part, with rock scrambles before you reach the open summit and its views of the Berkshires, Mount Everett and Mount Greylock to the north and the Twin Lakes to the east.
Parking and Fees
The trailhead lot holds about a dozen cars, according to the Lakeville Journal, and SummitPost notes that it can fill on summer weekends. SummitPost's route page says no parking pass or fee is required. Arrive early, and if the lot is full, do not block the shoulder of Route 41.
Appalachian Trail Rules
The top of this hike is on the Appalachian Trail, which the Connecticut Chapter of the Appalachian Mountain Club maintains. The chapter limits day-hiking groups to 25 people, bans open fires anywhere on the trail in Connecticut, and allows camping only at designated sites. The National Park Service requires dogs to be leashed on the AT's federally administered land and recommends a leash everywhere else on the trail, so keep yours leashed the whole way.
Weather on the Ridge
The open summit takes the full force of passing storms. In September 2025, rescue crews had to bring an injured hiker off Bear Mountain during a tornado-warned thunderstorm, according to the Lakeville Journal. Check the forecast before you start, turn around early if storms build, and bring a layer even in summer.
Hiking tips for Bear Mountain (Connecticut) via Undermountain Trail
- Start early on weekends; the Route 41 lot holds only about a dozen cars.
- Budget around five hours for the round trip, including time on top.
- Turn right at Riga Junction onto the white-blazed Appalachian Trail.
- Keep dogs on a leash on the Appalachian Trail.
- Head down before afternoon thunderstorms reach the exposed summit.
Nearby trails to explore
- Heublein Tower Trail (Talcott Mountain State Park)
- Will Warren's Den Trail (Rattlesnake Mountain)
- Ragged Mountain Preserve Loop
Hike this trail with TrailMates
Bear Mountain is in the far northwest corner of the state, so it is worth carpooling from Hartford. Post a state high point hike on TrailMates, use the event's group chat to sort out rides and an early start, and meet at the Undermountain lot on Route 41. Download TrailMates on the App Store or Google Play.