Beautiful Berkshires: A Driving Tour

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.

You might also enjoy: Why We Love the Swiss Hutte Inn: Cozy and Affordable Berkshires Escape

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 StockbridgeLenox, 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!

You might also enjoy: A Guide to Jiminy Peak

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!

You might also enjoy: Berkshires Winter Get-Away: Catamount + Great Barrington



Suitcases and Sandcastles 




  1. January 27, 2017 / 7:43 pm

    So many great towns in the Berkshires! You have to try Northampton sometime, my favorite 🙂 !

    • January 28, 2017 / 3:56 pm

      Thanks for the tip, I definitely will!

  2. January 28, 2017 / 1:09 pm

    We love a road trip too – this sounds like an amazing area, would love to jump in a car and explore here.

    • January 28, 2017 / 3:58 pm

      It’s a beautiful place to have exquisite countryside though so I can only imagine the trips you must take!

  3. January 28, 2017 / 5:47 pm

    It does look a beautiful part of the world, Corey 🙂

  4. January 28, 2017 / 10:51 pm

    Beautiful photos, thank you so much for this lovely tour! I have been to Vermont, New Hampshire and New York several times and it is just beautiful! Warm greetings from Montreal, Canada. 🙂

    • February 9, 2017 / 11:55 pm

      Thank you so much, Linda! I really appreciate your kind words. I’m sorry for the delay in getting back to you – I’ve recently been making some changes to my site. All the best.

  5. January 30, 2017 / 10:14 am

    This looks a gorgeous place Corey – can see why you love the Berkshires! Has a French feel to it too and I love the look of that book shop. I’d lose myself browsing in there for hours! 🙂

    • January 30, 2017 / 3:41 pm

      Thanks Rosemary – it does have some Frenchness to it, if that’s a word, which apparently it isn’t according to my spellcheck but will leave it anyways..very charming, like the French :).

  6. January 30, 2017 / 10:41 am

    beautiful photos!

  7. January 30, 2017 / 8:31 pm

    It sounds eclectic, idiosyncratic, curious, colourful – what a wonderful variation of destinations.

    • January 31, 2017 / 2:46 am

      It is all of those words indeed :).

  8. Ruth
    January 31, 2017 / 2:40 am

    After my visit to New York and Pennsylvania during the holidays, I think I fell in love with the East Coast. The weather was not the best but it didn’t matter because I was able to drive around a lot of rural areas in Pennsylvania with my mom and my sister. We stopped by the cutest towns wit lively atmosphere and tons of places to eat. That gives me a desire to discover more of other states in the area. Now, I have included the Berkshires to my list!

    • January 31, 2017 / 2:48 am

      Aw, thanks so much! So glad you had such a great visit. PA is beautiful land – we were just there in November. Next time you make it back definitely find your way to the Berkshires!

  9. February 2, 2017 / 10:05 pm

    Looks like Gilmore Girls country to me. Hopefully you don’t feel less of me now Corey. It was my trash tv choice for a while! Love this countryside. All the villages look so relaxed and cosy… and with not a crab cake to be seen! Ha ha Thanks for joining us on #farawayfiles

    • February 3, 2017 / 9:31 pm

      I’ve actually never seen Gillmore Girls but I hear they’re coming back! Have a great weekend Katy.

  10. Clare Thomson
    February 3, 2017 / 4:07 pm

    This is exactly the kind of New England I’m so desperate to see! The perfect share for #FarawayFiles

    • February 3, 2017 / 9:32 pm

      Glad you enjoyed it Clare – have a good weekend!

  11. February 7, 2017 / 8:10 am

    Haven’t been to the Berkshires, but love traipsing around Vermont and New Hampshire – New England in the Fall is pretty much perfection! Thanks for sharing about this lovely area for #FarawayFiles Corey, cheers from Copenhagen, Erin

    • February 8, 2017 / 12:17 am

      We are off to Vermont later this month – haven’t been in ages – looking forward to it!

  12. February 8, 2017 / 6:30 pm

    I would love to go to the Norman Rockwell Museum – I didn’t know it was there! He was my favorite artist when I was younger and I’ve seen a few of his traveling exhibitions.

    • February 8, 2017 / 11:09 pm

      You would love the Norman Rockwell museum! I’m a big fan of his work too, and the museum is such a nice tribute to him.

  13. February 8, 2017 / 8:42 pm

    I’ve never been but New England has always been so fascinating to me – would love to visit the region one day, especially in winter!!

    • February 8, 2017 / 11:18 pm

      New England is so beautiful during the winter – charming at its best!

  14. February 24, 2017 / 3:32 am

    We haven’t made it to the Berkshires yet. The area is high on our Fall Leaf-Peeping to-do list but, honestly, we’d love to go anytime! Love your views of the towns – absolutely charming!

    • February 26, 2017 / 9:36 pm

      Thanks so much, Rob! Berkshires will be PERFECT for a fall trip ;).

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