Three Shorter Berkshire Hikes

There are some great shorter hikes to enjoy in the area when you don’t want to spend the entire day on the trail. Here are three of my favorites. I want to offer a couple of alternatives to the ever popular Monument Mountain hike in Great Barrington. It’s a lovely hike but it can get crowded there. These hikes are a little more off the beaten path.

Tyringham Cobble

Disclaimer: I live in Tyringham and think it’s the most beautiful town in the Berkshires so this was an easy pick.

The Tyringham Cobble Loop from the Trustees of Reservations parking lot takes me about an hour. You will hike through a gorgeous meadow that depending on the season will be filled with Apple Blossoms, Goldenrod, or Fringed and Bottle Gentian flowers. My favorite approach is to take the loop in the clockwise direction. Once the trail goes into the woods, you’ll see the famous Rabbit Rock formation. After the rock you begin your ascent. At your first rock outcrop if you look to the east end of the Tyringham Valley you can sometimes make out the pillars of Ashintully Gardens (where Jebb and I are caretakers). Continuing  up to the summit you will be on the Appalachian Trail as well as the Cobble Loop Trail and check out the view of the Tyringham Church, cemetery and usually beautiful hay fields that make you feel like you are in a Monet painting. The trail loops down through hardwood forest and back to the meadow.

Length: 2.1 Miles. There are some more moderate/strenuous parts and even so I was able to take my niece and nephew on the hike when they were 5 and 7 with no trouble whatsoever.

You can extend the hike about another 2 miles by parking at the Appalachian Trail parking on Main Rd. I love the AT section here because you are in the heart of the valley on boardwalks and you get to take in the full scale of the landscape. This extension makes it more of a lolly-pop loop. I’ve even done sections of this hike on my Altai Hoks and it was great fun! Here’s a picture from the AT section in the meadows.


Hemlock Hill to Laura’s Tower 

This hike is a little longer than the Tyringham Cobble Loop. It’s about 5.5/6 miles round trip, but once you get up on the ridge, its great for moving at a good pace, so it is doable in about 3 hours. It starts in South Lee near the Oak and Spruce resort off of Pine Street. There is not much signage for this hike so you have to be a little adventurous. Where Pine Street meets Beartown Mountain Road there is a forest road gate on your right and a small parking area on your left. Shortly after you walk past the gate, on your left is a sign that says Laura’s tower 3 miles. It sharply begins to ascend the hill.

On a side note, this area was Beartown Mountain ski area and the trail basically follows up the old Panda Trail which was the beginner slope of a bygone era. After about 25 minutes the trail gets up on the ridge taking you through a breathtaking old growth Hemlock Forest. With some ups and downs you will pass an old stone town markers for Lee and Stockbridge.

The trail eventually meets up with Laura’s Tower, a steep metal staircase up to a beautiful look out. I like this hike because it’s longer and less travelled than the Laura’s Tower trail and it was on a “lost ski area” which always piques my imagination. The views from the tower are great and on a clear day you can see Mount Greylock to the north as well as Mount Everett to the south. There is a cool dial in the middle of the tower that shows where you are looking. Although the trail isn’t on the DCR map, the trailhead is located near the railroad hashes on north end of this map. The topo is accurate for the ridgeline. Here’s a shot from the tower last winter.


Round Mountain at McLennan Reservation

Another great Tyringham Hike! Again this hike is more on the short side where it takes me about an hour. You can always do it on a Wednesday or Saturday morning and then double up your visits and come visit me at Ashintully Gardens (June-Oct). What I love about this hike is the quiet feeling of solitude you get. There’s no road traffic sounds, just the sounds of the forest. It’s a very enjoyable winter hike and I highly recommend it in the spring because the waterfall will be rushing. I personally do this one year round; even in summer, it has never been too buggy. If you want to get your climb on, go counter clockwise; if you want a gradual ascent go clockwise on this loop.

In addition to the waterfall, there is an impressive beaver dam at Hale Pond with a nice bench to sit and birdwatch or rest. What I find interesting on this hike are all of the old stone wall and cellar holes from the former residents of Fenn Road who must have farmed here in the 1800’s.

I like to park (my bicycle usually) at the end of Fenn Road and walk up the road to add a mile to this 1.5 mile loop. It’s good for trail running too. The Trustees have posted wild life cameras here last year and I’m obsessed with this picture of my neighbor the bobcat.IMG_1200

One Reply to “Three Shorter Berkshire Hikes”

  1. 💙💙Wonderful descriptions – wish I was there!

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