Distance

6.5 Miles

Elevation Gain

1800 Feet

Activities

Hiking

Skill

Advanced

Season

Spring, Summer, Autumn

Type

Loop

Easy Parking
Forest
Scenic

Bear Mountain is the highest peak in Connecticut. The trail connects with the Appalachian Trail, scrambles over some great rock sections, and you've got to see the remains of the stone tower on the summit.

At 2,316 feet, Bear Mountain is the highest peak in Connecticut. The peak is about a half-mile south of the Massachusetts state line on the Appalachian Trail. The views are great. On a clear day you can see some of the peaks in southern New Hampshire. The remnants of a stone tower are on the summit. It was built in 1885 to mark the highest "ground" in CT. It is the highest peak, but the highest ground is actually the shoulder of Mt. Frissell just to the northwest of Bear Mountain. The 1885 marker at the top also gives the elevation at 2,354 feet (not bad for a 1880s survey, but we now know it's 2,316 ft).

I've hiked the trail in both summer and fall. The view from the top comes alive with shimming golds, glowing oranges, and deep reds during autumn.

There are some wild blueberry bushes along the Paradise Lane trail. If you're lucky and the bears and birds haven't eaten all of them you might get a handful, yum! I also crossed passed with several north bound AT thru-hikers.

Difficulty

This is a tougher hike. There is a good deal of elevation gain and some slick footing on exposed steep rock on the northern side of the mountain. If it's hot, bring plenty of water. The bugs can be out in force in the spring or early summer.

Directions

Start in the parking lot off Route 41 (Under Mountain Road) in Salisbury, CT for the Undermountain Trail (look for the blue oval sign). Follow the blue-blazed trail. You'll hit the intersection with Paradise Lane Trail. Follow the Paradise Lane Trail under the mountain until it intersects with the Appalachian Trail at the MA border. Turn south on the AT (white blazed) and start scrambling up some steep rock sections. Arrive at the summit of Bear Mountain. Follow the AT south to the junction with the Undermountain Trail. Follow the trail back to the parking lot.

Always practice Leave No Trace ethics on your adventures and follow local regulations.

Nearby Lodging

From $150/night

Glacial Erratic at Moore Brook

Salisbury, Connecticut

From $150/night

Echo Hill

New Marlborough, Massachusetts

From $100/night

Driftways Farm

Millerton, New York

Reviews

Leave a Review

Overall rating: 

Great CT Hike

I did this hike Sunday (8/21/16) and I'm still wondering why it took me 21 years of my life in CT to summit Bear Mountain! Beautiful hike with nice rock features towards the top and grand vistas. I'll definitely be using this mountain as training for larger summits in the future. Can't wait to get back in the fall and see the foliage...It looks spectacular based on your images.

Distance

6.5 Miles

Elevation Gain

1800 Feet

Activities

Hiking

Skill

Advanced

Season

Spring, Summer, Autumn

Type

Loop

Nearby Adventures

Adventure

Hike Mount Frissell to Brace Mountain

Adventure

Climb Alander Mountain

Adventure

Hike Alander Mountain

Adventure

Hike Mount Everett

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