An Afternoon in Stockbridge

A few weeks ago we took a road trip pit-stop in the Berkshires in western Massachusetts. I’ve been out in the Berkshires only twice, once for cross-country skiing in the middle of the winter, and for a James Taylor concert at Tanglewood. Both times driving through the surround area was a big lovely tease! After all these years of speeding through the Berkshires on our way to visit family, it was time to check it out.


The town of Stockbridge is a sleepy quasi-resort Americana town. Beyond the beautiful Berkshires, the area is best known for being the adult home of famous American Painter Norman Rockwell.


We stopped at the Elm Street Market for lunch, as the Yelp-recommended Once Upon a Table restaurant had already closed for the afternoon. The sandwiches were nothing to write home about, but if you are going on a picnic (or have arrived to Tanglewood unprepared) the Market has lots of picnic-size fixings.
There were a few small shops to pop into which, naturally, were filled with Norman Rockwell souvenirs. I’m hoping to return this winter for another ski trip and make sure I visit the Norman Rockwell Museum next time! (Information for admission and museum hours here.)


But my favorite reason to head out to western Mass is to visit Tanglewood! Tanglewood is an outdoor amphitheater with gorgeous Berkshire views from every angle! It’s widely known as the summer home of the Boston Symphony Orchestra. James Taylor also plays at Tanglewood every 4th of July – which is a blast if you can make it! There is a concert hall area with traditional seating, but why do that when you can picnic on the lawn!? Picnic-ers go all out – with small tables and champagne and candelabras.



Does it get more classic America than James Taylor and Norman Rockwell? Everyone has a different favorite Norman Rockwell painting. He has so many amazing pieces – some powerful, some silly. I had this one hanging in my bedroom growing up.

What’s your favorite Norman Rockwell painting?