STOCKBRIDGE, MA

“Quaint”

seems the correct word to describe this little town- but then you'd be missing out on all that it has to offer. Yes, the small town life is alive and vibrant - but you can't discount the rich history, the deep, professional art roots and the lush landscape that surrounds the town.

We start, as everyone should, with a stop for coffee at Stockbridge Coffee & Tea. Where you can browse for books while your cup is being prepared. Dogs are welcomed inside with a treat and a snuggle.

Next stop, the Lost Lamb, where a Le Cordon Bleu- trained pastry chef will dazzle and entice you with scents of fresh bread, butter croissants and an assortment of treats that all compete for your taste buds. The macaron (the size of a small salad plate) will keep you coming back as the flavors range from salted caramel and chai to raspberries and cream or pistachio with lemon curd.

Next, a little hike at Kennedy Park or Laurel Hill will get you hungry again for a sandwich or New England Clam Chowder in a fresh baked bread bowl at the Main Street Cafe.


A plethora of boutique stores and pop-up markets featuring locally-made, vintage and artistic finds will greet you here and in neighboring West Stockbridge, Great Barrington and  Lee, but save time for the Norman Rockwell Museum. This gem features hundreds of his Saturday Evening Post covers, a short documentary, dozens of large original works, and displays of his process. One of Rockwell’s former studios has been relocated to the grounds and a rotating exhibit featuring other artists also awaits you.

Here, you will also see his nearly 4 -foot long “Home for Christmas “ oil painting of Stockbridge’s Main Street. This piece is the centerpiece of the Stockbridge celebration, where for 4 hours, once a year, they bring in replicas of the cars in the painting to transport you to back in time. In fair weather, the event draws hundreds, but even in rain and cold, the event is charming, the people gracious, and the inclement weather provides the perfect excuse for ducking into the famous Red Lion Inn for a cozy chair next to a fire with a mulled cider or a Rockwell coffee.

What better way to start the holiday season in the Berkshires?


lifestyle, stills, travelJen Serena