Posted by: Jack Spratt | July 18, 2009

Getting Wonderfully Lost in the Berkshires of Massachusetts

The Berkshires in Massachusetts is a place once you visit you keep going back because you’ll find it soothing to get wonderfully lost in the atmosphere.

The view most people see of the region is from the Mass Pike as they travel to New York State going west or heading to Boston going east. And that’s about as far as it goes, and that’s a shame as it holds many riches as I discovered a number of years ago.

I love to weekend hike and prefer hills and mountains that are enjoyable to walk rather than prepare me for the next ascent of Everest. The Berkshires is perfect for my abilities and needs. I can even cope with the likes of Mount Greylock.

I have a few favorite places in the Berkshires that I’ll share with you today. You know things to do and places to stay.

One thing I enjoy doing in this region is just driving around picking out villages and small towns to stop for awhile and find a general store or a place to grab a coffee and sandwich and hang out. There are plenty of these as you travel south on route 8 which you can pick up at the town of Adams and then work yourself across and back up along Route 23, Route 112 and finally Route 116 back to Adams.

Favorite villages for me include: Cheshire, West Stockbridge, Sheffield, Monterey, Otis, Blandford, Russell, Huntingdon and Ringville on the road to Worthington. These places are about as far away from the larger towns in the Berkshires as you can get and a world removed from Boston and Springfield.

If you’re like me and enjoy walking but maybe not the fittest person in the world then you’ll enjoy Bartholomew’s Cobble in Sheffield and Mount Washington State Forest in Mt. Washington. The oddly named Bartholomew’s Cobble is ponds and easy rambling trails and a few hills to climb for views. Mount Washington State Forest has Bash-Bish Falls which I imagine would be spectacular during the foliage season. One of my goals is to get to the region during fall foliage season.

My final time spent when I visit is indulging in a little culture. I’d read this area is known for its outdoors during the day and cultural entertainment at night. However, I’m not a great Shakespeare or dance person but do enjoy galleries and in North Adams you have the Mass MoCA if contemporary art is your scene. This is a huge place and known for its controversial exhibits.

A short trip further north to Williamstown – another scenic town close to the Vermont border – you can visit the Williams College of Art and the Sterling and Francine Clark Institute. You may need a weekend to do these places and the town justice especially if you include Mass MoCA.

Of course there is all the other stuff such as Norman Rockwell Museum in Stockbridge and the Hancock Shaker Village but now you’ll need a week.

The Berkshires has a number of old stagecoach roads that were once used as overnight stops on the way to Albany when this was more of a pioneer region. Inns used to dot the coach roads and while many have vanished a few are left and reasonably priced if you’re looking for a weekend getaway.

The Red Lion Inn in Stockbridge and the Merrell Inn in Lee fit the olde New England stagecoach inn perfectly. The Red Lion Inn is large and does evening dining along with traditional bed and breakfast. The Merrill Inn only has eleven rooms last time I checked and offers just bed and breakfast. And for something special there is the Inn at Stockbridge.

I’m not sure when I’m going to get to the Berkshires again to tour around, but we haven’t picked a weekend fall foliage destination yet and as I’m writing this you know it sounds awfully tempting to spend it in my Berkshires. We’ll see.

Jacky “dude” Spratt



  1. […] Massachusetts: Cape Cod is quiet and beautiful in the fall but for color I have to pick the Berkshires. Ideal time to visit is around Columbus Day – second Monday of month – when peak foliage has arrived or is close to the rolling hills of this area. Consider the hike or drive up to Mount Greylock and the surrounding area of North Adams. See my recent post on the Berkshires here. […]

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