The Berkshires is in the far western part of Massachusetts, bordering New York; however, it’s only an easy 2 hour drive from the Boston area via the Mass Pike. It is a haven for artists who are looking for a low key lifestyle. It also provides an extensive amount of low key hiking (for the average hiker). Whenever, I’ve gone in the Berkshires, I feel a sense of community among the residents. It’s a small community that supports one another, advocates for social justice and the environment, and welcomes in all types of people.

I try to get out to the Berkshires for a few days every once in a while. Each time, I’ve set myself up in a different town and explored the local area. While it’s easy enough to navigate all of the Berkshires from one town, I’ve found that there’s more than enough to take in in each part of the Berkshires. If you look at the tourist magazine, you’ll see that they split the area up into 3 sections (north, central, and south), so I will do the same.

This post will focus on the Southern Berkshire area (from West Stockbridge to CT border)

For this year’s trip, I set myself up in Egremont – just south of Great Barrington because I wanted to explore Mt. Washington state forest – including Bash Bish Falls.

Bash Bish falls is the highest waterfall in Massachusetts. Until a few years ago, you could swim at the base & along the river; however, because people abused the area, this is no longer an option (since 2020). While this is disappointing, it means that when you get to the falls, you now have an unobstructive view of its beauty.

There are 2 hiking paths to get to the falls, so you’ll need to think about the type of excursion you’re looking for.

While you’re in the area, take a quick stop at Garret Gardens. This is a small arboretum featuring local trees and a labyrinth. It was a nice, peaceful addition to my Mt. Washington forest experience.

Mt. Washington State Forest is also how you get to the tallest point in Connecticut: the side of Mt. Frissell. While Bear Mountain is CT’s tallest peak, Mt. Frissell’s slope is the highest point at 2.380. Hiking this area can also include the Tri-state marker for CT, MA & NY. Mt. Frissell’s peak doesn’t have a view, but if you pair it with other mountains in the area (Round, Brace, Bear) & go on a clear day (unlike me), you should have some nice views.

Two other hiking spots I checked out during my visit are both Trustees of the Reservation sites: Monument Mountain & Tyringham Cobble.

Monument Mountain is just north of Great Barrington Center on rt 71. If you’re not a Trustees member, parking is $6 (pay by credit card). Monument Mountain contains a few trails, but the most popular one because its a loop & includes views it the 2.6 mile Hickey & Peeskawso Peak Loop w/Devil’s Pulpit detour. From the parking area, you’ll want to decide if you want an easy path up or down.

Either way, you’ll reach the rocky peak and look out over a nice view of the area. Be careful with the rocks and the cliff edge. These elements make this a little tricker of a hike. Also, bring bug spray.

Note: On the way to Tyringham Cobble, look out for Santarella (the Gingerbread house).

Tyringham Cobble includes a 2 mile loop that takes you above the rolling hills and orchards of the valley. It also allows you to walk a small – a very small section – of the Appalachian Trail. While I’m never going to take on the grand adventure of hiking the Appalachian Trail, I’ve always been intrigued by what it would be like. Getting out on sections of the trail and talking with people who are hiking it is as close as I’ll ever get to the experience. And on this hike, I was lucky enough to encounter a thru hiking couple to talk to about their experience. At this point they have 600 miles to go, which sounds like a lot to us lay people, but for those who have already completed more than twice that, it means that they are nearing the end. The hike includes a few viewpoints, blackberries if you’re hiking in the late summer, and an aptly named rock formation – rabbit rock.

About 5 minutes away from Tyringham Cobble is another Trustees property: Ashintully Gardens. Close to the road is a small well manicured garden set among the trees and flanking a small stream. While there aren’t many flowers here, the varied greens of the scene as well as the small reminders of the past make this a beautiful and peaceful site. If you’re up for a small hike, the property also includes the ruins of the “Marble Palace” – a mansion build by the Tytus-McLennan family in the early 20th century. Central to these ruins are a set of pillars that create a stark contrast to the rolling hills in the background.

One last Trustees property I checked out this time was Naumkeag in Stockbridge. Naumkeag was the summer home of the Choate family until the late 1950s. When Mable Choate died in the late 1950s, she bequeathed both the property and the furnishings to the Trustees, which means that all of the rooms are exactly as she left them over 75 years ago. The 1st & 2nd floor of the house and the gardens are open for exploration. Be sure to reserve your ticket ahead of time because parking is limited.

Built into a hill, the view of the valley creates a stunning backdrop to the grounds. It also makes for a challenging walk around, so be aware of this if you have mobility issues. The grounds are composed of different types of gardens – there is a Chinese, evergreen, and rose garden to name a few. The grounds also include a small woodland path (including a pet cemetery) as well as set of fountains built into stairs that are flanked by birch trees (this was my favorite viewscape).

The staff provides historical walking tours of the house and grounds a few times a day, and are available for questions at any time.

The Berkshires is full of historical houses and walks. One of the notable figures from the area is Civil Rights Activist and scholar, W.E.B Du Bois. There’s a whole brochure that outlines a collection of notable places from his life in the area. I checked out 2 of them: the Housatonic Riverwalk & his Boyhood Homesite.

The Riverwalk goes from Cottage street to Bridge street in Great Barrington center. The walk is pretty short (just over 1/2 mile one way) & is broken up by a neighborhood stretch, but the plaques discussing W.E.B Du Bois’ love for rivers, William Stanley’s role in the history of electric power, tree and plant identification signs, and the peaceful view of the Housatonic river make it a nice quick detour from GB center. On the other side of Bridge street, the path continues as the riverfront path, so the walk can be extended.

Just south of Great Barrington center is W.E.B Du Bois Boyhood Homesite. While only the foundations of the house remind, UMASS has put together a 1/2 mile walk through the woods with plaques along that way that give a more extensive overview of DuBois’ professional work. The path also includes a commemorative bolder dedicated to Du Bois’ work in 1969.

Sheffield is also home to the Big Elm Brewing & Berkshire Mountain Distillers, so if you’re looking for local beer & spirits, check them out. Both places offer a large selection of drinks (Berkshire Mountain Distillers has more than 5 types of Gin alone as well as whiskey, rum, and bourbon) and are happy to talk you through your choices. Sheffield is also home to Roberto’s – a small pizza restaurant that boasts interesting ingredients and a friendly atmosphere.

The main street of Great Barrington & Stockbridge are places to spend an afternoon. Stockbridge is the smaller of the two, but has a handful of stores and cafes to check out. Also, the Red Lion Inn features an art gallery in its 2nd floor hallway ( British illustrator Ralph Steadman’s work was on display during my visit). The building itself is a New England picturesque with its grand front porch filled with people enjoying food and drinks with the view, a large front lobby and a back formal dining room. Just off the lobby is an old elevator encased in a steel cage. The stairs to the 2nd floor at its left.

Great Barrington center boasts more specialty stores than Stockbridge (cheese, wine, alpaca, books, etc.) and includes several restaurants both on its main street as well as a few side roads. Steam Noodle Cafe was one of the highlights of the culinary part of my journey. Just off the main street is the Berkshire Food Co-op, which is a nice place to get some snacks and food during your stay. I was also able to pick up some interesting spices from their bulk food aisle to take home.

One of the surprising finds in the Berkshires was the number of French style bakeries, so don’t miss out on picking up a croissant or tart along your journey.

If you’re looking to extend your day into the night, The Egremont Barn offers live music Wednesday – Saturday night. Their week starts with an open mic night every Wednesday night from 7-10pm. The Barn opens at 5pm & sign ups happen soon afterward, so if you’re interesting in performing (2 songs), make sure to get there early. This space is cozy with great acoustics and the audience is supportive to all the artists – from teenagers to retirees. On the grounds is also a rescue farm – Maggie’s Farm – when you can see some goats, cows, chickens and the like.

Before heading home, I decided to make one more stop in West Stockbridge to check out the Hotchkiss Mobile Gallery. Work by owner Joel Hotchkiss as well as other local artists are on display, and Joel even welcomes the public into is studio the process and to ask any questions. Just down the street is the old Shaker Mill, which housing Shaker Mill Books. The Mill building itself includes art installation constructed from books as well as some old and rare editions. Don’t forget to check out the stop motion video of what books do at night.

While West Stockbridge doesn’t’ have any lunch restaurants, No. Six Depot serves up some baked goods and coffee while West Stockbridge Public Market serves up some interesting hot and cold sandwiches.

Google Maps of places mentioned in this post

Recounting all of this makes me realize how much there is to do in the area, and there were still places that I didn’t have time to check out. Next time I’m in the area, I want to make sure to give myself time to check out the Berkshire Botanical Garden, Turn Park Art Space, and Laura’s Lookout Tower. If you have other spots that should be added to my Berkshires list, send them my way. It’s a beautiful area that I look forward to returning to.

The Trustees of the Reservations

I’ve mentioned The Trustees several times in this post, so I wanted to give them a shout out. Founded in 1890, The Trustees of the Reservations protects historical and natural spaces throughout Massachusetts. Every Trustees property I have been to has been well maintained, thoughtfully laid out and easily accessible. They have places throughout the state, so you should check out what they have to offer wherever you end up in Massachusetts.