What To Do In the Berkshires

...and where to eat, for seriously advanced planners.

Museums, Historic Sites & Gardens

  • Norman Rockwell Museum in Stockbridge, MA. Experience Norman Rockwell’s original paintings and discover changing exhibitions of other masters of illustration. A top regional attraction.
  • Visit the mansion and breathtaking gardens of The Mount, Edith Wharton’s renowned Lenox, MA estate. 
  • MASS MoCA, in North Adams, MA, about an hour drive. Housed in a restored 19th century factory, it is the country’s largest center for contemporary visual and performing arts. A very popular destination for Berkshires visitors. 
  • Take a stroll through the Berkshire Botanical Garden in Stockbridge, MA. One of America’s oldest botanical gardens featuring 23 seasonal display gardens, classes, and special exhibits.
  • The Berkshire Museum in Pittsfield, MA. Art, history and natural science. Aquarium, antiquities, fine art, Hall of Innovation with activities for all ages. Growing up, James was a particular fan of the dinosaur statues out front. 
  • The Clark in Williamstown, MA. Fine arts museum of Williams College, often with excellent seasonal exhibits.
  • Spruce Ridge Farm Alpacas in Old Chatham, NY.  Alpacas + interesting & unusual breeds of cattle, pigs, chickens, guineas, a few dogs and cats. A farm shop full of alpaca yarn, clothing, toys rugs and more.

Performing Arts

  • Even though the Tanglewood season officially opens the following weekend, there is usually something exciting happening. Classical, popular, and jazz concerts June to Labor Day at the summer home of the Boston Symphony Orchestra and the Tanglewood Music Center. If nothing's doing, still worth going for a stroll through the grounds and checking out the views of the Stockbridge Bowl.
  • Shakespeare & Company in Lenox, MA. 4 to 6 shows daily Tues.-Sun. May-March. The best Shakespeare & new plays. Picnic on 30 acres. Free family shows. 
  • Williamstown Theatre Festival in Williamstown, MA. Tony Award-winning theatre offers performances each summer featuring top national talent. 
  • Jacob's Pillow Dance Festival in Becket, MA. International dance festival and Nat’l Historic Landmark; 300+ free and ticketed performances, talks, exhibits, tours & onsite dining.
  • Barrington Stage Company, Pittsfield, MA. Award-winning theatre presenting top-notch musicals, masterful classics, thought-provoking new work and youth theatre on three stages.
  • Mahaiwe Performing Arts Center in Great Barrington, MA. Year round arts center & restored historic theater presents films & live events.

Nature & Recreation

  • Hike Mt. Greylock (an hour drive), the largest mountain in Massachusetts. Or drive to the top, enjoy the lookout, and walk around the short trails without having to exert yourself, like we do.
  • Pick organic strawberries at Thompson-Finch Farm in Ancram, NY. 
  • Golf at our local public courses: Cranwell Golf Club in Lenox, MA, Greenock in Lee, MA (9 holes), or Donnybrook (9 holes).
  • Arcadian Shop in Lenox, MA. Arcadian shop, equipping adventurers for 30+ years with gear, clothing, footwear & travel needs. Bikes, kayaks, lots of rentals, with trails out back.
  • Appalachian Trail, 90 miles of footpaths that run through western Massachusetts.
  • Undermountain Farm in Lenox, MA. Lovely farm near Tanglewood. Licensed instruction hunt seat & dressage. Guided trail rides. Riding day camp. Indoor/outdoor arena. Boarding & turnout. We've not been, but sure sounds nice.
  • Berkshire Scenic Treks & Canoe Tours in Lenox, MA. Guided canoe and kayak tours. Enjoy the Housatonic’s abundant untouched beauty. Daily/evening. 

Yoga & Spas

Shopping

  • Guido's Fresh Marketplace in Pittsfield, MA. Our favorite! They were Whole Foods before there was Whole Foods. High quality fruits, vegetables, meat, fish, healthy prepared foods & groceries. 
  • The Berkshires Farmers' Markets. Located throughout the region, official farmers' markets and roadside stands.
  • Bartlett's Orchard in Richmond, MA. Berkshires Best Apples. Mostly we go in the fall. But they have good stuff all year, especially their cider and cider donuts. Seasonal vegetables and pumpkins. We ship apples.
  • Soma in Richmond, MA. Our wedding caterers! They also have this lovely storefront with ready made dishes, and high quality local groceries.
  • Go antiquing in Hudson (45 min drive).
  • Charles H. Baldwin & Sons in West Stockbridge, MA. Est. 1888. World famous vanilla! People come from far and wide for this. Extracts, maple syrup, & more in an-fashioned country store.
  • Berkshire Co-Op Market in Great Barrington, MA. Natural foods store & café featuring local & organic produce, meat & seafood, prepared foods & extensive wellness department.

Restaurants (by town & roughly in order of our familiarity)

  • Mario's Restaurant in New Lebanon, NY. A Waldinger family favorite for generations. Family built tradition since 1964 serving fine Italian-American cuisine. 
  • Spoon in Lenox, MA. We've had great breakfasts and lunches here. Unique breakfast, lunch & ice cream from the best ingredients available, sourced locally, organically & humanely. Foodie owned and operated.
  • Patisserie Lenox in Lenox, MA, & Great Barrington, MA. AMAZING pastries and lunch sandwiches & salads. A delicious French-Russian family fusion. 
  • Church Street Café in Lenox, MA. American bistro under new mgmt, creative menus for lunch/dinner. Fresh local ingredients, extensive wine list, al fresco dining. Owner operated.
  • Firefly in Lenox, MA. Vibrant, chef-owned Church St. landmark.
  • Nudel, Lenox, MA. People rave about this one (we've not been). Nudel is a creative American pasta bar which takes its inspiration from the bounty provided by the local farms and producers of Berkshire County.
  • Alta Restaurant & Wine Bar in Lenox, MA. Mediterranean cuisine with a variety of local and organic ingredients. Extensive wine list. A Lenox favorite.
  • Baba Louie's Pizza in Great Barrington, MA, PIttsfield, MA, and Hudson, MA. Great casual place for pizza and salads. Wood fired organic sourdough pizza, creative soups, salads & sandwiches made from the freshest local ingredients. Vegan/gluten free options. Good for kids too.
  • Rubi's Coffee & Sandwiches in Great Barrington, MA. Hole in the wall place off a parking lot that has great coffee & sandwiches. 
  • Allium Restaurant + Bar in Great Barrington, MA. Farm-to-table, seasonal menu of contemporary American cuisine, paired alongside small-production & biodynamic wine list. 
  • Castle Street Cafe in Great Barrington, MA. Casual cafe, award-winning wine list. Piano jazz bar with live music nightly. Seafood, pasta, steak. Chef owned.
  • Cafe Adam in Great Barrington, MA. Winner of Wine Spectator Award of Excellence, "a sanctuary for quality food and drink," featuring locally grown and organic ingredients and both classical and modern cooking techniques. 
  • Six Depot Roastery & Cafe in West Stockbridge, MA. Our recent favorite. Outstanding coffees, teas, sandwiches, salads. A really cool space too, complete with a neat art gallery. If you're passing through West Stockbridge, make sure to stop by! 
  • Rouge in West Stockbridge, MA. Per Zagat's: "Chef William Merelle's "mouthwatering" French cuisine coupled with spouse Maggie's "warm hospitality" makes this West Stockbridge bistro a "popular" "go-to" for the "elite and hoi polloi" alike; a relatively recent expansion doubled the rouge-accented space, although it still gets "jammed" in the "lively" bar where the less "expensive", "interesting tapas menu" is "a treat", leaving only "loud" decibels and sometimes "lackadaisical service" as issues."
  • The Old Inn on the Green in New Marlborough, MA. World class dining in restored 1760 Inn, candlelit dining rooms with fireplaces. Seasonal dining al fresco on outdoor terrace.
  • John Andrews Farmhouse Restaurant in South Egremont, MA. Fancy & good. New American regional cuisine. Wine Spectator award for excellence & Zagat’s best of the Berkshires. Dinner, bar & farm menu. 
  • The Old Mill Restaurant in South Egremont, MA. The Old Mill has been a Berkshire dining favorite for thirty-five years. Chef-Owner Terry Moore serves seasonal, contemporary New England cuisine as well as traditional favorites. Rustic elegance in a 1700’s grist mill.
  • The Red Lion Inn in Stockbridge, MA. James Beard House-honored chef, 3 restaurants, contemporary regional cuisine, elegant & casual indoor & outdoor dining, award-winning wine list. The Lion's Den At The Red Lion Inn is traditional pub fare & drinks in a casual setting.
  • Mezze Bistro + Bar in Williamstown, MA. Farm-to-table contemporary American cuisine emphasizing seasonal & local foods.