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There’s so much delicious local food in the Berkshires of western Massachusetts. This is a fantastic destination for healthy family travel.
The Berkshires of western Massachusetts is a region that’s worth visiting during every season of the year. Spring and fall offer stunning colors as nature comes to life in spring and fades with the foliage in autumn. Summertime in the Berkshires is a festive season with so many special activities to enjoy. And in the winter, the Berkshires offers outdoor fun on the slopes and indoor recreation at museums and other cultural attractions.
After a summertime visit last year, I knew I wanted to return during the winter months with my family. Even with the bare trees and hay-colored fields, the Berkshires offers breathtaking scenery in the winter. There’s something special about being in a mountain landscape during this slower time of year.
Applegate Inn Bed and Breakfast in Lee is a wonderful central location for a visit to the Berkshires. Perched atop a hill near downtown Lee, Applegate is a 1920’s estate converted into a B&B. They’re members of Berkshire Grown, and they source local ingredients for the delicious daily breakfast spread. In the summer, they use produce grown in the gardens on their large estate. We received such a warm welcome here, and it felt like home as we were able to spread out in a comfortable two-bedroom suite. My kids loved playing games in the fancy living room and lounging around the suite during the evenings.
Allium Restaurant in downtown Great Barrington is one of the best restaurants to visit if you’re looking for amazing locally sourced food in the southern Berkshires. My family had our best meal here, and we loved everything we tried. The hen of the woods mushrooms and fried pickled red onions were followed by fish and pork tacos, an epic burger, and a delicious bowl of pasta and sausage. The food and ambiance were both exceptional.
Prairie Whale in Great Barrington is a rustic restaurant that serves comfort food straight from the farm. The setting and menu are relaxed enough to bring the kids, and the wood stove makes for a cozy atmosphere on a cold winter night.
John Andrews Restaurant is a renowned farm-to-table establishment in South Egremont. Located in an old farmhouse, this menu features ingredients from many local farms throughout the Berkshires, the Hudson Valley, and northern Connecticut. It looks like a great place to celebrate a special occasion.
51 Park Restaurant and Tavern in Lee is a cozy restaurant that serves homemade comfort food. Located just down the hill from the Applegate Inn, we enjoyed dinner here our first night in town. The chopped salad, risotto, and lobster macaroni and cheese were all highlights. This family-friendly restaurant isn’t far from the Mass Pike, so it’s a good alternative to highway food if you’re passing through the area.
The Red Lion Inn has been an institution in the Berkshires for over 200 years. This beautiful old inn is home to multiple restaurants that offer casual and formal farm-to-table dining experiences. They use many local, sustainable ingredients on their menus, and outdoor dining is available in the courtyard during the warm weather months.
Markets and Cafes
Rubi’s Cafe in Great Barrington looks like a wonderful spot for breakfast or lunch. Their menu features classic breakfast dishes including local eggs and carefully selected cheeses, plus house-made lunch meats for sandwiches. I want to visit here during our next trip so I can test their claim that they have the best grilled cheese anywhere.
Taft Farms in Great Barrington is exactly the kind of place I’m looking for at lunchtime when I’m on vacation. This small market has a deli with delicious sandwiches made from store-roasted meats, local veggies, and homemade bread. In the growing season, many dishes are full of vegetables from the fields at Taft Farms. We enjoyed four of their delicious sandwiches for lunch on our ski day. My husband got the avocado sandwich, and the woman at the deli cut into 3 or 4 avocados before she found one that looked good enough to put on the sandwich. It’s refreshing to eat at a restaurant that goes to such trouble to make sure the ingredients are high-quality.
Marketplace Kitchen and Cafe in Sheffield is a casual cafe serving sandwiches, flatbread pizzas, and salads made from locally sourced ingredients. They offer weekly movie nights and family dinner nights to help bring the community together. We had a great meal at their sister store in Pittsfield last summer.
Berkshire Mountain Bakery in Housatonic makes delicious, easily digestible sourdough bread in several different varieties. My family took a tour of the bakery and learned about the baking process from owner Richard Bourdon. This bakery was featured in Michael Pollan’s documentary, Cooked, and it’s a model for how bakeries can produce healthy bread in large quantities. We sampled the cherry pecan bread, the sesame loaf, and a variety of cookies. All were delicious!
The Bistro Box is a roadside shack in Great Barrington. Open for lunch and dinner during the warm weather months, they serve affordable, locally sourced food including grass-fed burgers, fries, soup, paninis, and fair trade coffee. This is a great place to pick up an affordable meal in spring, summer, or fall.
The Berkshire Co-Op Market in Great Barrington is full of healthy, natural food options. Their cafe is open for breakfast and lunch, and it features organic, sustainably grown fruits and vegetables. This is also a good place to stock up on healthy snacks for the road.
SoCo Creamery is a destination for ice cream in Great Barrington. They serve handmade micro-batch ice cream made locally in the southern Berkshires. We had a delicious sampling from their menu after our dinner at Allium. The ice cream is so rich and delicious!
Berkshires Between Meals
During the winter, there are lots of indoor and outdoor activities to enjoy during a trip to the southern Berkshires. Skiing is the first thing that comes to mind for many families this time of year. The Berkshires is a central place to meet up for a ski date with friends or relatives from New York, New Jersey, Connecticut, and Massachusetts. The ski mountains in this region tend to be less crowded than the mountains in northern New England, and they’re very family-friendly.
My family enjoyed a beautiful ski day at Catamount Ski Area. Located on the border between Massachusetts and New York, skiers can actually pass from one state to the other while skiing down the mountain. This was such a great location for our ski day given the range of abilities in our group.
It’s been a rough season for ski areas because of the light snowfall amounts, but Catamount is known for the care it takes in grooming the trails despite the weather challenges. The trails were beautiful and the lift lines were minimal even though it was a beautiful day. My son declared it one of his favorite ski mountains, so I’m sure we’ll be back before long.
When you’re ready for a break from skiing, downtown Stockbridge and Great Barrington are beautiful old New England towns worth exploring. Antique stores, book shops, and other unique businesses make for a fun afternoon of window shopping. Stockbridge is also home to the Norman Rockwell Museum, which has the largest collection of original Rockwell paintings in the world.
While it’s not located in the southern Berkshires, the Magic Wings Butterfly Conservatory is a worthwhile detour on your way out of town if you’ve got kids in the car. This butterfly oasis in South Deerfield is a fun place to come in out of the cold and get an up-close view of butterflies in their natural tropical vegetation. After our visit to Magic Wings, we stopped at Paul & Elizabeth’s Natural Foods Restaurant for lunch in nearby Northampton for some healthy food before heading home.
Local Food in the Berkshires
We enjoyed so many local food experiences during our weekend in the southern Berkshires, and we’re already talking about our next visit to western Massachusetts. It’s so close to Boston, but it feels like a world away!
Disclosure: My family was hosted by the Berkshires Visitors Bureau and several of the businesses mentioned in this post. All opinions are my own.