Hiking Bear Mountain; 3 Routes Up CT’s Tallest Peak!

woman and dog on top of bear mountain in connecticut in summer

Located in picturesque Litchfield County, Connecticut, Bear Mountain stands proudly as CT’s highest peak at 2,354 ft. In this post, we will outline three different routes you can take to hike Bear Mountain in Salisbury, CT.

Whether you’re a Connecticut local like me, live in a neighboring New England state, or visiting from far away – Connecticut’s tallest mountain is an essential and fun hike to put on your list!

I’ve hiked Bear in all conditions from a really hot summer day (actually was concerned I didn’t bring enough water that day 👀) to snowy conditions in winter where you couldn’t see a thing from the peak.

Remember that Bear Mountain is located in the hills of northwest Connecticut on the Appalachian Trail. So if you’re coming from lower and more central locations in CT like me, it will be colder and is often the first area to see snow in the winter.

So to help you complete your Bear Mountain journey, we will explore 3 distinct routes to the top.

We’ll also review parking information for Bear Mountain as this can be a popular hike on weekends.

⬇️ Quick breakdown of the 3 hikes up Bear Mountain🐻

Route 1: Bear Mountain Trail Loop

  • 🥾6.1 miles, 1,693 ft elevation
  • ✅ Long but beautiful route along the Appalachian Trail
  • ❌ Parking crowded on weekends, overflow parking is along Route 41
  • 🚙 Navigate here: 42.02876, -73.42887

Route 2: Bear via Mount Washington

  • 🥾2.9 miles, 574 ft elevation
  • ✅ Shortest route, loop
  • ❌ Not accessible from Connecticut if going in the winter. The CT side of East St is closed in the winter and you have to go up into MA first & access East St from there
  • 🚙 Navigate here: 42.04936, -73.4671

Route 3: Sage’s Ravine & Bear Mountain

  • 🥾 4.59 miles, 1,138 ft elevation
  • ✅ See multiple waterfalls in Sage’s Ravine
  • ❌ Don’t pick this one if you’re not great at reading the map or navigating trails! 🙂
  • ❌ Not accessible from CT in the winter. Must access thru MA
  • 🚙 Navigate here: 42.04936, -73.4671

Guides for each of the 3 hikes up Bear Mountain! 🐻⛰

1. Bear Mountain Trail Loop (longest route)

  • Miles: 6.1 mile loop
  • Elevation Gain: 1,683 ft
  • Time: ~3.5-4 hours
  • Difficulty rating: Hard (short scramble if coming down from summit going clockwise)
  • Parking: Navigate here: 42.02876, -73.42887 (parking lot on Rt 41/Under Mountain Rd)
  • Dog-friendly: yes

This route begins in northwest Connecticut, with parking off of Under Mountain Road in Salisbury. If the lot is full, you can park along Under Mountain Road on the side of the road, parallel to traffic. You will see cars lining the street here on a popular weekend day like Mother’s Day or the first mild Saturday in spring.

After parking- let’s begin the loop which takes you up and over Bear Mountain’s craggy summit in just over 6 miles.

After a tough 1.1 miles in and 700+ feet of elevation you’ll come to the start of the loop section. Taking the loop clockwise, bear left and walk for about 0.7 miles at which you will come to and met up with the white blazed Appalachian Trail.

You’ll turn right onto the AT here and follow the AT northward where you’ll reach Bear’s summit in 0.8 miles.

At the summit, climb up (easy climb!) the large pile of rocks to take in the panoramic views of the surrounding landscape including views of North and South Lake in Salisbury.

At the top, you’ll notice a stone plaque at the base of the pyramid or pile of rocks.

plaque on top of bear mountain in ct

According to the Historical Marker Database, Mason Owen Travis built a stacked-stone pyramidal tower at the summit of Bear Mountain in 1885 and placed the stone marker.

“Over the years, the tower deteriorated and began to collapse. After attempts at restoration the eastern corner disintegrated in 1978 and much of the tower collapsed, leaving the plaque in the ruins.”

So when ready to complete the loop climb down the big pile of rocks and continue on the trail running behind it and heading north on the AT.

It’s heading down after the summit of Bear where things get a little tricky! 🧗🏽🪨

This is where the rock scramble is as you descend a tricky 500 feet in under half a mile. Get your poles or a big stick ready! (The dogs have always been fine running up or down this but smaller dogs could have a hard time).

trail sign at bear mountain in CT

Just past the bottom of this scramble (about 0.5 miles from Bear’s summit), you’ll reach a trail juncture.

(See sign pictured here),

Take a right onto the trail here, leaving the Appalachian Trail!

As you can see from the sign, RT 41 where you parked is about 3 miles away now. 🙂

Once you leave the AT, you’ll be on this new trail for about 1.8 miles until you reach the first trail you were on.

From here, turn left and follow the path back towards your car. Congrats, you made it and hiked Connecticut’s tallest mountain! 😍👏

2. Bear Mountain in CT via Mount Washington State Forest in MA

  • Miles: 2.9 mile loop
  • Elevation Gain: 574 ft
  • Time: ~1.5 to 2 hours
  • Difficulty rating: Moderate (short scramble going UP to summit if you take the loop clockwise)
  • Parking: Navigate here: 42.04936, -73.4671 (parking on East St/Mnt Washington Rd)
  • Dog-friendly: yes

⚠️❄️Note: East Street is not well maintained in winter. It is also a very bumpy and rough road that can have lots of potholes. My Prius was able to handle it without any snow on the ground. But if this area gets a lot of snow, it may not be passable and the road may be closed.

This route has its trailhead right along the border of CT and MA in Mount Washington State Forest in South Egremont, MA. Taking the parking directions linked above, you’ll arrive at a pull-off along East Street.

If coming from MA, the parking area will be on your left and fits about 5-6 cars. If coming from CT, the parking area will be on your right.

The entrance to the trail is in the right corner next to a gate which makes it hard to miss. 🙂

Follow this AT connector trail for about 0.7 miles. I love this little walk. You’ll walk along a brook that feeds into Sage’s Ravine below and pass a large AMC cabin (AMC Northwest Camp) on your right. I’ve always wondered what it looks like around the camp but never ventured up there. Reservations are required and I never wanted to disturb campers who were already there!

So still along this initial 0.7 miles you’ll continue along until you reach the juncture with the AT. Turn right here on the AT (joining the white blazes). You’ll be heading south on the AT into and toward Bear Mountain in CT.

Here is where you’ll abruptly begin a steep 500-foot and 0.5-mile ascent to Bear’s summit. There is a short scramble at the very top but it can be easier going up rather than coming down.

The dogs have always been able to navigate this scramble up or down. It’s those of us on just 2 legs that have a tougher time!

After taking in the summit and views atop Bear, you will pick up with the rest of the trail. Climbing down from Bear Mountain’s pile of rocks take a left to continue your journey on the Appalachian Trail (white blaze!).

You’ll gently descend for the next 0.6 miles until you come to a trail juncture.

Turn right here (onto trail known as Bear Mountain Rd) to exit off of the AT and make the loop back to where you parked.

You can enjoy a nice, mainly flat, 0.8-mile walk until you reach East Street. Turn right and walk along the road for just a little bit (get dogs on leash at this point!) until you reach the small lot on your right where you parked.

3. Bear Mountain and Sage’s Ravine Falls 💦

  • Miles: 4.59 miles
  • Elevation Gain: 1,138 ft
  • Time: ~3.5 hours
  • Difficulty rating: Moderate, short scramble going up (and coming down) Bear
  • Parking: Navigate here: 42.04936, -73.4671 (parking on East St/Mnt Washington Rd, the CT side of this road is closed in the winter and you will need to access it by going up & into MA first. Access East St thru the Massachusetts side, not CT side)
  • Dog-friendly: yes
waterfall on sages ravine hike
sages ravine waterfall hike

This route combines a walk down to Sage’s Ravine where you’ll turn right and walk all along Sage’s Ravine Falls in Massachusetts. You’ll then go back up the way you came and head up to Bear Mountain!

Or, you can go up to Bear first and then take the leisurely walk down to Sage’s Ravine. You’ll love the sound of all the falls in there!

And dont worry, the walk up to Bear is only 0.4 miles and about 500 ft of elevation so it will be a bit steep but not for long! When we hiked here I remember it was 10:30 before we started the walk up Bear and I needed to be back at the car before noon and we were back shortly after 11:30.

👏Congrats! You just summited Bear Mountain, the tallest in Connecticut. 🙂 🥾🏆

Things to remember:

  • Challenging Terrain: The routes here have some diverse terrain and not wide flat paths. Rocky outcrops and challenging prolonged ascents add exciting elements to both journeys, making for robust and well-rounded adventures.
  • Seasonal Changes: Bear Mountain is a year-round destination, with each season providing its own unique charm. While spring offers blooming wildflowers (and mountain laurel!), summer brings lush greenery. Fall is beautiful but can be very crowded. ❄️Note that in winter the road from CT is closed and you will have to go up and into MA first to access East Street.
  • Encounter other friendly hikers: Since Bear Mountain is on the popular Appalachian Trail in CT, you’ll likely encounter other hikers (and likely through hikers hiking the whole AT in the summer).

Embrace the beauty of the highest peak of our state and the trails that lead you there! The Appalachian Trail is such a treat to walk on and offers a true New England hiking experience!

Once done, I hope you have a new appreciation for the rugged adventure and natural wonders Connecticut has to offer. 😍 🥾

Bear Mountain FAQs

How long does it take to hike Bear Mountain in CT?

The shortest loop outlined here can be completed in 1.5 hours. The longer 6.1-mile loop can be done in an average of 3.5 to 4 hours.

What is the elevation gain of Bear Mountain CT?

For the shorter loop, the elevation gain up Bear Mountain is just about 574 feet. For the longer loop the elevation gain is just under 1,700 feet.

When is the best time to hike Bear Mountain in Connecticut?

Due to the popularity of summiting the tallest mountain in Connecticut, it is best to hike Bear Mountain during non-peak times on weekdays or very early on the weekend. Going in winter is a great time to hike without the crowds!

Looking for more hikes on the Appalachian Trail in CT?! Check out this post here on 7 different day hikes on the AT in CT!

Hike Connecticut's Appalachian Trail 7 Beautiful Day Hikes

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