Beautiful Berkshires: A Driving Tour

We love driving in the Berkshires…

One of my favorite past times is to take road trips and go exploring. I love driving around and discovering new towns, whether it be in New England, out west, down south, wherever. I like to just bumble around in the car and see what’s out there, get the flavor for a region, a city, a village. Sometimes I don’t even get out of the car, but most of the time I do. It’s this insatiable curiosity I guess I’ve always had, and one I’ve subjected my family to for years now!

They’re used to it, and I think (I hope) like it just as much as I do now. One of the places we’ve become fond of driving around in is the Berkshires in western Massachusetts. This scenic, mountainous region with its quaint, artsy towns is ideal for exploring around – so if you enjoy road tripping like us, you’ll want to head here for some good old-fashioned New England charm.

The Berkshires is a beautiful area filled with small mountains, quirky villages and miles and miles of country land, trees and blue sky. City dwellers from Boston and New York have second homes and retreats here, and it’s known as an artists’ haven with museums ranging from MASS MoCA – one of the largest contemporary art spaces in the country – to the Norman Rockwell Museum. Tanglewood, the summer home and festival of the Boston Symphony Orchestra, is here, as are other cultural festivals and arts-related events.

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There are several towns in the Berkshires which dot the area, all filled with funky bookshops, crafts boutiques, charming inns and gourmet restaurants. Don’t let the countryside fool you – there is great food to be had in the Berkshires! (Our favorite to date has been John Andrews, a delicious farm-to-table restaurant located on the edge of Great Barrington near Hillsdale, NY). Country stores, old mills, mercantile shops and mom and pop diners are scattered about, all oozing that old-school charm you hope never goes away.

The first town we ever visited in the Berkshires was Great Barrington, full of good restaurants and antique shops, and from there we were hooked. We knew we had to drive around and explore more of this serene area, and so we have. There are the adorable towns of Stockbridge and West Stockbridge, Lenox, North Adams where MASS MOCA is, Egremont and Sheffield. There are many more towns, but these are the ones we have mainly been to.

You might also enjoy: Stockbridge, MA: Wintertime in the Berkshires

The funny thing is, we haven’t even driven around the Berkshires in the summer months, or the fall, which is when it’s at its prettiest with all of the fall foliage. We’ve only been there in the wintertime, to go skiing. But it’s just as lovely this time of year too, Christmas décor still lingering about, early morning frost lifting through the trees. Especially when it’s snow covered, some might say it’s just as picturesque to visit then as it is when it’s full of orange, yellow and purple hues.

Last winter when it was bitingly cold out and too freezing to go skiing, we holed up in Stockbridge at the historic and utterly charming Red Lion Inn, where we drank Bloody Mary’s – the best you’ll ever have, I swear – and ate French onion soup, all the while listening to live piano music. We visited the Norman Rockwell museum as well, and meandered about town, all of which prompted me to write Stockbridge: Wintertime in the Berkshires (see above).

This year we drove around tiny Egremont and got pancakes at Mom’s Country Café, took a country walk in West Stockbridge, ate lunch at the Red Lion again, drove through and stopped in Lenox to peruse the fabulous The Bookstore (with the greatest owner ever, who completely catered to my kids in their wonderful children’s section) and drove through scenic Sheffield, where the Berkshire School is located, for anyone wondering. We took the back roads where we found lake vistas, hiking trails and farmland, which I can only imagine is as green as can be during the warmer months. Long, winding roads that seemed to roll on forever brought us to one town after the next, one cozy meal after the next, one beautiful setting after the next. We really love the Berkshires!

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If you’re looking for a relaxing, country escape with both culture and picturesque drives, make sure to head to the Berkshires. Most towns are about 15-20 minutes away from each other, and to drive from the southern part of the Berkshires to the northern part is about an hour and a half. For a great list of scenic driving tours, check out Berkshire Scenic Driving Tours. I plan to use this as my guide in the fall for a foliage driving tour!

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