Blankets, Baskets, and Boots: A Proper Picnic in the Berkshires

Whether you’re a seasoned al fresco aficionado or just someone who loves a good sandwich on a gorgeous day, the Berkshires is brimming with perfect picnic spots—from winery lawns to sculpture gardens to riverside trails. Here’s where to lay down your blanket and dig into summer.

Balderdash Cellars tucked into the hills of Richmond, has generous tasting hours as well as a rotating lineup of food trucks and music on the weekends. Bring a blanket, good friends, and enjoy incredible views for miles. 

Les Trois Emme Winery in New Marlborough is open Saturday and Sundays, 12-5, and offers tastings, occasional live music, and some of the friendliest hosts in the region. Before you sample some Grenache Rose, stop by The Southfield Store (yes, it’s in Southfield just a stone’s throw away) and treat yourself to one of their epic sandwiches and heavenly pastries–mini apple pie, salted caramel coffee cake, pistachio croissants. 

Norman Rockwell Museum

Of course, the most iconic Berkshire picnic experience is catching a show on the Tanglewood lawn. Over the years, devotees have upped their picnic game to include candelabras and brocade tablecloths, but don’t sweat the food. Just bring a blanket or chairs and a side of take-away-gourmet from Guido’s Fresh Marketplace, Berkshire Food Co-op, or the Marketplace Specialty Store, all located in Great Barrington. And since it’s on the way, stop by Spirited in Lenox for some serious craft beer or Cotes du Rhone Rouge. Want to go all out? Call ahead and order one of their custom charcuterie baskets for the road/show. 

For the first time in a few years, the art stars have aligned in the region, and several major museums and historic properties–including TurnPark Art Space in West Stockbridge, Norman Rockwell Museum in Stockbridge, Chesterwood in Stockbridge, The Mount Edith Wharton’s Home in Lenox, and The Clark in Williamstown–boast vibrant outdoor sculpture exhibitions framed by monolithic whimsy. These exhibitions are (mostly) free to visit, and wandering is highly encouraged, as is picnicking. If you are visiting up north, Craft Food Barn in North Adams prides itself on having full-to-the-gills patrons, or grab a hummus wrap or some classic chicken salad (and a specialty coffee) at Wild Oats Coop. 

The Mount, Edith Wharton’s Home

If you are a picnic traditionalist, and only the great outdoors and a blanket in the sunshine will do, lace up your hiking boots to find the perfect spot along your trek. Many vista roads and conservation properties in the region are open for the season, including the C.M. Gardner State Park in Huntington, which has trails and picnic spots along the Westfield River. The Pleasant Valley Wildlife Sanctuary in Lenox boasts 1,000 acres of forests, meadows, mountains, wildlife, and birdsong. A recently completed all person’s trail makes this a property that everyone and anyone can enjoy. 

Wherever your picnic takes you—winery, museum, mountaintop, or music lawn—don’t forget the essentials: bug spray, good food, and sensible shoes. Oh, and don’t forget the sandwich. 

Explore more cuisine #intheberkshires here!

Return to the Berkshire Blog.