The Berkshires

Clark Art Institute

The Clark Art Institute is a special museum situated in the rolling hills of the Berkshires where you can view world-class art. Featuring famous artists from both Europe and America, the collection of Sterling Clark is on full display for you to enjoy. Join us for our experience at this Berkshires Art Museum, and learn all about the Clark in Williamstown!

High Lawn Farm

At our on-site farm store, the Farmstead Creamery, we offer all of our artisanal dairy products as well as a variety of other locally produced goods. Enjoy a farm-fresh ice cream cone or artisanal cheese board at one of our picnic tables as our Jersey girls roam in the fields behind the shop. Then have a walk around our idyllic property, see where we milk our herd, and enjoy some of the best views in the Berkshires.

MASS MoCA

The Massachusetts Museum of Contemporary Art is a museum in North Adams, Massachusetts. It is one of the largest centers for contemporary visual art and performing arts in the United States. MASS MoCA exhibits art by both well-known and emerging artists, focusing on large-scale, immersive installations that would be impossible to realize in conventional museums.

The Mount, Edith Wharton's Home

The Mount is a historic house museum and vibrant cultural center with a variety of tours, programs, and events for you to enjoy. The Mount is one of the most authentic, restored Gilded Age cottages around. Enjoy lunch on The Terrace, serving seasonal fare and refreshments against the backdrop of the gardens.

Naumkeag Pumpkin Show

Explore our famous gardens as we transform Naumkeag into a celebration of autumn with over 1,500 jack-o-lanterns, hundreds of mums, pumpkins and countless gourds – most of which were grown right here at Naumkeag! Hot cider and fall treats will be available for sale on-site. Due to the age of the site and its steep and uneven terrain, Naumkeag is not ADA compliant and is not wheelchair- or stroller-accessible and may be difficult to access for guests with limited mobility.

Norman Rockwell Museum

A warm welcome awaits you at Norman Rockwell Museum. Be surprised and delighted at the magnificence of Rockwell’s large scale original paintings and discover the highly relatable world of American Illustration – the art that tells our stories. There’s always something new to enjoy with ten galleries of ever-changing special exhibitions, engaging programs, a scenic 36- acre campus, and more. Share memories and make new ones.

Wyndhurst Golf & Club

2023 Golf Rates Rates include cart usage fee April, May, October Midweek - $55.00 Weekend - $75.00 Twilight - $45.00 (2:00 pm)

Ashuwillticook Rail Trail

Discover this 10.8-mile point-to-point trail near Berkshire, Massachusetts. Generally considered an easy route, it takes an average of 3 h 15 min to complete. This is a popular trail for birding, cross-country skiing, and road biking, but you can still enjoy some solitude during quieter times of day. The trail is open year-round and is beautiful to visit anytime. Dogs are welcome, but must be on a leash.

Bash Bish Falls State Park

Bash Bish Falls is a great short hiking trail to the highest waterfall in the state of Massachusetts. Starting at the lower parking area off of Falls Road, this short hike follows a rugged trail along Bash Bish brook through mature forest and over boulders, tree roots, natural stone stairs, and long wooden steps.

Hilltop Orchards Home of Furnace Brook Winery

We invite you to visit our 100-year-old, family run orchard with breathtaking views of three states. Plan a day or an afternoon of apple cider sipping, wine tasting, cider donut eating, cidery touring, hiking, strolling, relaxing and rejuvenating at the foothills of the Berkshires.

Hancock Shaker Village

Home to the Shakers for more than 220 years, Hancock Shaker Village is now an outdoor history museum dedicated to preserving the Shaker legacy and making that story relevant and illuminating for today's visitors. Situated on 750 acres of picturesque farm, field, and woodland in the bucolic Berkshires of Massachusetts, the Village consists of 20 historic buildings, a working farm and heirloom gardens, and a premier collection of 22,000 authentic Shaker artifacts. The museum, Seeds Market Cafe, and Shaker Mercantile are open every day, 10-4 in spring and 10-5 in summer and fall.

Ioka Valley Farm

There is no general admission during our fall weekends. Our mini-corn maze is free, as well as our dress-me scarecrows, giant pumpkin house, and visiting the farm animals. If you pick a pumpkin from the patch you pay by the pound and if you choose a pumpkin from the gift area they are all pre-priced. We have three activities that we do charge to participate in: Family Fun Play Area, Wagon Train Ride, and Pumpkin Slingshot.

The Best Places to eat and Drink in the Berkshires

Chocolate Springs Cafe

The Café is a spectacular destination for chocolate lovers. Not only can you purchase and enjoy all our chocolates, confections, ice cream, gelato, and hot chocolate but we have comfy couches, tables for gathering, live music many evenings, newspapers and magazines. Open 7 Days a week, Monday-Sunday 9:00am to 9:00 pm.

Christiansen's Tavern at Jiminy Peak

Pub food at it’s finest! Giant nachos, burgers, bountiful salads, creative sandwiches and wraps, vegetarian specialties, award winning chicken wings and a huge selection of draft beers. Our rustic tavern awaits you.

Brava Wine Bar

Brava is an extremely popular wine bar located in the heart of Lenox. Kitchen serves food until midnight. Come in for our wide selection of wine by the glass, beer on tap, tapas, pizzas, cheese, and charcuterie. Seating is first come first served--we don't typically take reservations.

Haven Cafe Bakery

Heavenly—favorite for quick, casual. Open for breakfast and lunch: Monday through Friday 7:30am-3pm, Saturday and Sunday 8am -3pm.

Mario's

Enjoy made-to-order sandwiches on homemade bread at Mario's Restaurant in New Lebanon. Mario's Restaurant is a jackpot for those looking for low-fat and gluten-free meal options. Toast your evening out at this restaurant with a glass of beer or wine from their lengthy drink list. Bask in the sun (or moon!) light when you dine on Mario's Restaurant's outdoor patio.

District Kitchen & Bar

Mazzeo's Ristorante

Family-owned, Italian cuisine prepared with the freshest ingredients. Open for dinner daily, 4:00-9:00, Friday and Saturday until 10.

Proprietor's Lodge

The Lion's Den

Balderdash Cellars

Bringing food and non-alcoholic beverages to the winery is permitted, however, bringing alcoholic beverages (beer, wine, hard seltzers, spirits, etc, etc) is strictly prohibited.

Berkshire Mountain Distillers

An authentic, regionally focused maker of small-batch, award-winning craft spirits. Visit our distillery for a complimentary tasting and self-guided tour — Open Daily 11 am – 5 pm

Big Elm Brewing - Great Barrington Taproom

Guido's Fresh Marketplace

A family-owned independent marketplace featuring beautiful produce, natural and specialty food, prepared food, a full-service florist, meat and seafood, and wine and beer.

Shire Donuts

Warm, fresh, made-to-order donuts with hundreds of build-your-own topping combinations. It's not just a donut - it's an experience. Also serving coffee and daily baked-good specials. Treat yourself - because you deserve a better donut.

On A Roll Cafe And Catering

The caterer of our wedding and where Marja starting working as a waitress at 15 years old. On a Roll is an eclectic breakfast and lunch cafe located in the heart of the Berkshires, On a Roll Cafe and Catering Company has been serving fresh and exciting menu items for over 16 years. We strive to provide our customers with the highest quality food possible by making everything from scratch in-house; Monday-Saturday: Breakfast: 7 - 11, Lunch: 11-4. Sunday, Breakfast: 7-1