Bartholomew’s Cobble – A Hidden (Must-Do) Berkshire Hike!

Hidden amongst gently curving country backroads at the southernmost tip of the Berkshires in Sheffield, Massachusetts, sits a 357-acre peaceful preserve to explore. Well removed from Route 7, you’ll find Bartholomew’s Cobble with views you would never have imagined!

I lived in the Berkshires for four years and never hiked here nor recall ever hearing about it.

One reason it could be a hidden gem is that (I’ll tell you about its one negative upfront!) it does not allow dogs for the protection of wildlife that have made a home there.

Another reason could be that it’s located in the southernmost part of the Berkshires – drive any further south and you’ll be in CT!

Nevertheless, Bartholomew’s Cobble is a Berkshire hike that had me in awe from the moment I set foot on the trails. From the moment I pulled into the lot and pristine grounds surrounded by scenic rolling hills and farmland, I could tell I was someplace special.

About Bartholomew’s Cobble:

Location: Located in Sheffield, MA. Click here for directions to the parking lot.

Designated as National Natural Landmark designation in 1971 because of its immensely diverse flora, Bartholomew’s Cobble is one of the special properties owned and maintained by The Trustees.

Not only does one of North America’s greatest and most wildly diverse collections of fern species and flowers call this wilderness home, but there is an awe-inspiringly epic view from atop this preserve’s highest point.

Bartholomew’s Cobble Views ⛰

The northerly facing panoramic vista awaits welcomingly atop Hurlburt’s Hill, which rises 1,000 feet above a beautifully preserved twenty-acre field on the Massachusetts-Connecticut divide.

The view gives you an up close and detailed look of the Riga Plateau to your left, and stunning longer-range views of the southern Berkshires to your center and right.

The mountains you see in the distance include Bear Mountain (CT’s highest point!), Race Mountain, Mount Everett, and Jug End. All of these are totally worth the hike if you’re up for a challenge someday! 🙂

Bartholomew’s Cobble Loop Trail 🥾

There are 5 miles of trails you can hike here but the most popular that takes you by the river and up to the view is the Bartholomew’s Cobble Trail.

It’s a 3.5-mile loop with about 472 feet of elevation gain. While labeled as ‘easy’ on AllTrails I would still wear sturdy boots as there are rocks and roots and there can be muddy sections as well.

Bartholomew’s Cobble Highlights 🥾

🌊 Housatonic River: A true highlight that adds to the Colonial mystique of this property is the gently ambling Housatonic River that coils along the banks of these trails.

Creating beautiful oxbows through the farm fields and general landscape, from a thousand feet skyward, the waterways look like a giant serpent, although absent any malice or Slytherin-ish intent. 🙂

I’m a major sucker for a river walk so this type of feature on an adventure hits me just right! 

🌲250 yo Cottonwood Tree: Another highlight of this trail loop is the 2nd oldest Cottonwood Tree in the state of Massachusetts at about 250 years old! This beautiful beast is certainly worth checking out and commands respect as a veteran of the Revolutionary War. 

⛰😍 View from Hurlburt’s Hill: Rising property’s 1,000 feet, Hulburt’s Hill is the Cobble’s highest point. Walk up this 20-acre upland field that features panoramic views northward up the Housatonic River Valley.

Bartholomew’s Cobble Loop Details 🗺

Check out the Bartholomew Cobble map to follow along!

This is a beautiful, family-friendly area, with very well-maintained, wide trails, suitable for all walks of life to enjoy safely.

I was surprised to learn and am disappointed to have to share with you that our furry companions are not allowed to enjoy all the natural wonders here with us…

The only silver lining I can imagine here is that if you ever need a break from your needy, adorable hounds, Bartholomew’s Cobble would certainly fit the bill as a quiet, meditative getaway and remains on my list of most beautiful and accessible places around. 

To start the hike you’ll head to the left of the cabin where you park and begin the trail.

There are a few trail choices when you begin the hike here but if you just stay straight you’ll be on the main loop which will be leading you first to the Housatonic River after just 0.1 miles.

(Or, if you want to walk right to the hill with the view then take the trail to the right of the parking lot and walk for just a mile. I plan to take this route to catch a sunset someday!)

But back to the main loop, the trail will wind its way clockwise with the entire first mile or so being entirely on the banks of a wide-flowing tributary. 

It’s along this first section, around .6 miles, where you’ll spot the great Cottonwood lording over a trail crossroads.

From the wild and lush lowlands you’ll head into the shaded wonder of the woods at about 1 mile in.

You’ll reach the Hudson River Valley panoramic vista at 2.4 miles.

When walking back down the hill, stay to your left and soon you’ll find yourself approaching your car. 

Where to eat after your Bartholomew’s Cobble Hike:

If you need a snack (I always am!) following your 3.5-mile trek, head just north to Great Barrington’s Guido’s Fresh Market Place. Guido’s is like a mini town within a town, boasting a fully functional food court, cafe, bakery, craft shop, and ever-present cheese samples!

Enjoy!