Best Outdoor Dining in the Berkshires

These open-air restaurants in the lush Berkshire Hills offer tantalizing food, views, and amusements.

By Kim Knox Beckius

Aug 06 2018


The Courtyard at the Red Lion Inn | Best Outdoor Dining in the Berkshires

Photo Credit : Courtesy of the Red Lion Inn
In the Berkshires region of western Massachusetts, where landscapes and townscapes look like paintings come to life, it’s only natural to want to spend as much time outdoors in the summer as possible. So why head inside at mealtimes? There’s something about dining outdoors — sunlight sparkling off water glasses, breezes tickling napkins, sounds and scenes vibrant and alive — that elevates a meal to an experience. When the weather turns warm, these eight Berkshire-region restaurants put their own playful spin on outdoor dining.

8 Best Spots for Outdoor Dining in the Berkshires

Best Outdoor Dining in the Berkshires
The Courtyard at the Red Lion Inn | Best Outdoor Dining in the Berkshires
Photo Credit : Courtesy of the Red Lion Inn

The Courtyard at the Red Lion Inn

If Willy Wonka had a garden café, it would look something like this: red, bubble-shaped umbrellas; lion statuary; abundant flowers in every known shade of pink; director’s chairs lined up in front of the cutest backyard bar. The bartender would conjure up a rainbow of icy cocktails. And a petite menu of temptations would fulfill every wish, whether you’re craving something light or something hearty, locally raised meat or a creative vegetarian dish. Luckily, you don’t need a golden ticket to dine in the outdoor courtyard of this venerable Main Street inn. (Reservations, though, are a good idea.)

Trattoria Rustica

Is it the courtyard setting, with its brick walls, leafy plantings, and billowy white market-style umbrellas? Or the scrumptious bread, baked crisp every day in the sort of brick oven you’d see in Italy? Either way, dining outdoors at this authentic Italian restaurant is a transportive experience. You could drive by this restaurant every day and never realize there’s a green oasis tucked inside, where patrons clink wine glasses and salivate over heaping pasta plates and brick oven–roasted favorites like veal loin chop rubbed with red wine, vinegar, garlic, and herbs.
Best Outdoor Dining in the Berkshires
The Bistro Box | Best Outdoor Dining in the Berkshires
Photo Credit : Kim Knox Beckius

The Bistro Box

When you see baskets filled with Frisbees and lawn dice hanging from shade trees, you know you’ve found a fun place to dine outdoors. And when you learn the chef has a policy of not cutting sandwiches in half — because the presentation won’t be as attractive — you realize this is no ordinary roadside grab-and-go (if the perpetual line out front wasn’t already a dead giveaway). So take a plastic knife to that toasted sub roll stuffed with sirloin, sweet onions, and cheddar ale sauce if you must share. Or plan to arrive hungry and with time on your hands because you don’t want to miss the seasoned handcut fries or the ice cream from local Maple Valley Creamery, either. Plus, there are rounds of cornhole to be played, and six bucks gets you a bucket of balls for the golf driving range.

The Old Inn on the Green at the Pillow

That’s a mouthful of a name for the Berkshires’ ultimate fine outdoor dining experience: a collaboration between one of the region’s top chefs and Jacob’s Pillow, where dance fans flock each summer. Peter Platt, chef-owner of the Old Inn on the Green in New Marlborough, brings his finesse with the Berkshires’ bounty to this open-air tent on the Jacob’s Pillow campus. Even if you don’t have tickets to a performance, make reservations for a full-service, farm-to-table brunch or dinner adventure beneath this enchantingly lit canopy, where you can pair dishes like lemon polenta with grilled summer vegetables or grilled rib-eye with caramelized onion bordelaise with a dozen wines available by the glass. Try to time your visit to coincide with a free performance on the Pillow’s outdoor stage.
Best Outdoor Dining in the Berkshires
Prairie Whale | Best Outdoor Dining in the Berkshires
Photo Credit : Kim Knox Beckius

Prairie Whale

One look at the worn lawn around the ping-pong table and cornhole boards, and you’ll know some epic games have been played in the front garden at this homey restaurant, set back from Great Barrington’s busy Main Street. String lights give the outdoor patio a festive look, and daily-changing dinner and weekend brunch menus here are equally whimsical. Restaurateur Mark Firth, an urban escapee, raises some of the kitchen’s raw materials at his own Berkshires farm. Foodies struggle to select from such farm-to-table inventions as scallops with paprika tomato fish broth, fried potato, squash, and basil, and brick chicken with roast sweet potato, grilled scallions, and spinach. Order a Salty Fairy — mixed with Berkshire Mountain Distillers’ Greylock gin — and take your time deciding.


Every outdoor table at Sloane’s has a view of beautifully manicured greens and tree-lined fairways. You don’t have to play 18 or even nine holes at the Cranwell Spa & Golf Resort’s 1926-designed course to dine on the deck at this casual restaurant, but there’s something satisfying about earning your Ipswich clam po’ boy, frothy beer, and bucket of sweet potato fries. Half a dozen vegetarian items and even more gluten-free options make the menu universally pleasing.
Best Outdoor Dining in the Berkshires
Terrace Café at the Mount | Best Outdoor Dining in the Berkshires
Photo Credit : Sarah Edwards

Terrace Café at the Mount

There are few views in the Berkshires to rival the one that novelist Edith Wharton fashioned at the estate where she lived from 1902 to 1911. The formal, French-style flower garden with its 3,000 blooms and the Italianate hidden garden were conceived by Wharton to provide a visually pleasing transition between her elegant home and the distant lake and woods. Imagine dining on the mansion’s back terrace, looking out over this glorious scene. Thanks to a culinary partnership with Main Street Hospitality, you can. It’s one of the Berkshires’ best-kept secrets that the Terrace Café at the Mount is open each day during the summer season between 11 a.m. and 4:30 p.m., and there is no admission fee required to dine on the fresh, light fare du jour.

Stone Hill Café at the Clark

The framed scenes that hang inside the Clark Art Institute have nothing on the views from this seasonal outdoor patio at the museum’s Stone Hill Center. Look north toward Vermont’s Green Mountains, and west toward New York’s Taconic Range. The cool mountain air will ignite your appetite for lunch delights and fresh-baked treats, prepared with rural ingredients and city sophistication. Starr Events, the catering arm of Stephen Starr’s New York City restaurant empire, provides the culinary masterpieces. Your meal will fuel you if you’d like to hike trails through this 140-acre campus: They’re open free to the public. Where’s your favorite place for some outdoor dining in the Berkshires?

SEE MORE: Where to Stay in the Berkshires | Hotels & Inns Guide to Mass MoCA | New England’s Ultimate Art Experience5 Favorite Outdoor Activities in the Berkshires