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Our Berkshire Favorites

Food

Not only is the Berkshires known for its cultural scene, think Tanglewood, Nathaniel Hawthorne, Mass MoCA, and Berkshires Art Festival to name a few, it has also been popular for its farm to table culinary world. Below are only a few of our favorite places to eat and things to do. 

Pizza Favorites

  • Roberto’s Pizza – 113 Main St, Sheffield, 5 min ride. Great pizza selections or make your own. Our favorites are Hannah Bella and Pollo Loco. They also sell ice-cream from our favorite farm, High Lawn (see below for more info on High Lawn).

  • Baba Louie’s Pizza – 42 Railroad St, Great Barrington, 7 min drive. Great sourdough pizza spot. Best to put in your order earlier as they get very busy between 7-8 pm

 

Sandwich/Brunch/Quick Bite favorites

  • The Marketplace Cafe – 18 Elm Ct, Sheffield, 5 min ride. Delicious sandwiches, wraps, salads. There are a few locations of which one is in Sheffield and the other one is in Great Barrington. A favorite is the Oooh, Mexico sandwich.

  • Marjoram and Roux – 47 Railroad St, Great Barrington, 5 min ride. Delicious brunch spot using fresh and local farm products. Highly recommended

  • GB Eats – 282 Main St, Great Barrington, 5 min ride. Great better-than-a diner-type of restaurant with a variety of tasty food options. Luca loves their Mickey Mouse shaped pancakes.

  • The Red Lion Inn - 30 Main St, Stockbridge, MA 01262, 20 min ride. The Inn is one of the most quintessential Berkshire hotels in the area. Great for a dinner or brunch in their outdoor garden.

 

Mexican Restaurants

  • Agaves Mexican Grill - 389 Stockbridge Rd Great Barrington, 12 min ride. Our favorite Mexican place. Amazing food and great outdoor seating.

  • Xicohtencatl Mexican Restaurant - 50 Stockbridge Rd, Great Barrington, 12 min ride. Another great authentic Mexican spot. Delicious margaritas and lovely outdoor seating area.

 

Fine Dining Favorites

  • Café Adam - 420 Stockbridge Rd Ste 3, Great Barrington, 12 min ride. Amazing food and great outdoor seating available.

  • The Prairie Whale – 178 Main St, Great Barrington, 7 min ride. Pricey but great food. Plan ahead and make a reservation.

  • John Andrews Farmhouse Restaurant – 224 Hillsdale Road, South Egremont, 11 min drive. Selected as one of the World’s 25 Best Farmstead Restaurant Experiences by The Daily Meal. Beautiful outdoor seating available.

 

Casual Dining Favorites

  • Barrington Brewery – 420 Stockbridge Rd, Great Barrington, 11 min ride. Nice outside seating, great handcrafted beer selection, and a variety of food options.

  • The Egremont Barn – 17 Main Street South Egremont, 7 min ride. Our go to spot in the summer with outdoor seating and live music.

 

Bakery/Ice-cream Favorites

  • Soco Creamery – 5 Railroad St, Great Barrington, 5 min ride. A must stop for delicious locally made ice-cream.

  • Bakin’ Bakery - 117 Main St, Sheffield, 5 min ride. Instagram handle is bakinbakery413 where you can see their creations. Great cakes, cookies, baguettes, and more. Their seasonal cookies and cakes are awesome (Halloween, Christmas, etc.). Wonderful local business!

  • Pixie Boulangerie – 198, Main St. Great Barrington, 7 min ride. Great bread and pastries! The bakery is located in the new Flying Church building right next to the Prairie Whale restaurant.

 

Boozy Favorites

  • Big Elm Brewery – 65 Silver St., Sheffield, 7 min ride. Solar powered brewery that makes 6 of their staples year round plus tap room only releases. All of their beers are crafted to reduce gluten.

  • Berkshire Mountain Distillers – 356 S. Main St, Sheffield, 6 min ride. Not only do they produce a wide array of award-winning spirits, they also have a very diverse garden program. They focus on growing cocktail/spirit-centric herbs and botanicals in their greenhouses and gardens. Drop by for a visit, pick up some of their seasonal herbs, get some expert cocktail advice or just taste through their line of spirits.

  • Sunset Meadow of Massachusetts - 296 South Main Street
    Sheffield, MA 01257, 5 min ride. Sunset Meadow Vineyards is among New England’s largest producing vineyards, with over 170 acres of rich and fertile soil. Currently, with over 50 acres planted, they produce sustainably grown and estate-made wines that have made them one of the most recognized and awarded vineyards in the northeast.

 

Groceries

  • BigY – 740 S Main St, Great Barrington, 5 min ride. Standard supermarket with ‘normal’ prices and big selection of food/house essentials

  • Guido’s – 760 S Main St, Great Barrington, 5 min ride. Great local, fresh, and organic produce and food selection, pricier than BigY

  • Berkshire Food Coop –34 Bridge St, Great Barrington, 6 min ride. Lots of great organic food options and foods you likely won’t find at BigY and/or Guido’s, on par or more expensive than Guido’s

  • Rubiner's Cheesemongers & Grocers – 264 Main St, Great Barrington, 6 min ride. Our absolute favorite cheese shop that also sells the best bread around, specialty pasta, wine, and chocolate. This shop embodies everything that our family is. 

 

Farmers Markets

  • Sheffield Farmer’s Market – 125 Main St, Sheffield. Winter market at Dewey Hall 10am - 1pm on the second Saturdays of December 11, January 8, February 12, and March 12

  • Great Barrington Farmer’s Market- 18 Church St, Great Barrington. Every Saturday, 9-1 pm through November 13.

Food
Leaves
Adventure

There is so much to do in the Berkshires all year round. We have only scratched the surface with the below list. We will keep adding as we explore! 

Skiing

  • Catamount – Route 23, South Egremont, 10 min ride. Besides skiing, the mountain offers the longest zipline in the US, over 5,500 feet long and a vertical drop of over 1000 feet. 

  • Butternut – 380 State Rd, Great Barrington, 15 min ride

 

Swimming/Paddle Boarding 

  • Lake Garfield – 78 Tyringham Rd, Monterey, MA, 25 min ride. This is our favorite local lake with a public beach, parking passes are not needed. Lifeguards are on duty during the summer season. The beach is small but sandy and perfect for kids. The lake is perfect for swimming, canoeing, or paddle boarding. 

  • Benedict Pond – Benedict Pond Road, Benedict Pond Rd, Great Barrington, 30 min ride. This is a shallow man-made pond that connects to the Housatonic River. Previously a swamp, trees were cleared in the 1930s and a dam was built. The water is very clean and calm so perfect for swimming or paddle boarding. The area also has designated picnic areas with grills.

 

Hiking

  • Benedict Pond and the Ledges – 1.7 mile loop trail around the Benedict pond, 30 min ride. Hikers along this trail can enjoy water views almost the entire length around. It I beautiful all year round and we do it with our 5 year old.

  • Monument Mountain – Monument Mountain Reservation, 3.8 mile long trail of a moderate hike. We did it with our son and with some complaining we did it! In his defense, it was also snowing and very cold so a bit harder to summit it.

  • Bash Bish falls - 4G85+29, Mt. Washington, MA 01258, 25 min ride. Beautiful moderate 2.1 mile hiking trail. This is the highest waterfall in Massachusetts and a popular scenic destination. The dramatic final pitch of Bash Bish Brook drops about 80 feet into an emerald plunge pool. Enjoy a hike to experience the wonder and beauty of this deep, verdant gorge. Nearby, Taconic State Park in New York state offers more visitor amenities, picnicking, swimming, and camping.

  • Race Brook Falls, Lower Falls - 716-732 S Undermountain Rd, Sheffield, MA 01257, 11 min ride. Moderate 1.3-mile out-and-back trek that leads to a ~80-foot tall waterfall. Hikers will find parking directly off Route 41 in a small pull-off at the coordinates provided.

 

For the little ones

  • The Sheffield playground we often go to is located on 91 Fredrick Lane, 5 min ride. When you turn onto the Fredrick Lane you will reach a dirt road at some point. Keep going and a beautiful baseball field, basketball court, picnic area and very nice and new kids playground will be at the end of the road. It is usually not crowded at all and was a nice COVID playground for our son.

  • Great Barrington playground or Town Hall Park is located behind the Town Hall on 334 Main Street, 5 min ride. This is a perfect location because it is so close to all the restaurants on the Railroad.

  • Stockbridge playground is located on 52 Main St, Stockbridge, 15 min ride. It is within a walking distance from the main Stockbridge shops and restaurants so perfect for both the kids and grownups.

 

Entertain/Relax/Enjoy

  • Tanglewood - 297 West St., Lenox, Massachusetts 01240, 30 min ride. Tanglewood is the summer home of the Boston Symphony Orchestra and the Boston Pops. From spring through fall, Tanglewood hosts a large variety of live music performances.

  • Berkshires Art Festival - Ski Butternut, Rte. 23, Great Barrington, 15 min ride. This top East Coast summer art event is rated by the Berkshires Visitors Bureau as one of the 10 Great must-see Cultural Hotspots in Western Massachusetts.

  • Miraval Berkshires Spa and Resort -55 Lee Road, Lenox, Massachusetts, United States, 01240, 25 min ride. Perched atop 380 protected acres in the Berkshires, the digital device-free resort is home to several restaurants, a Life in Balance Spa, and multiple pools—making this bucolic hillside setting ideal for unwinding and relaxing. A must visit!

 

Farms

  • Taft Farms – 119 Park St N, Great Barrington. Open 7 days a week, 8am-6pm. Buy farm fresh produce or eat already made food by their chef on the farm using all of their own grown foods.  

  • High Lawn farm – 535 Summer St, Lee, 20 min ride. A must visit for both kids and grown-ups. The farm is huge with baby cows to pet, gorgeous views, and delicious food. Get a scoop (or two if you have a huge appetite) of their delicious ice cream or fresh ghee, milk, eggs, cheese, and a bunch of other delicious foods at their farm shop. We go there every weekend in summer.

  • Windy Hill farm - 686 Stockbridge Rd, Great Barrington, 20 min ride. Great for berry or apple picking. It is also a design and garden shop. Beautiful flowers and gorgeous views from their berry farm.

  • Hilltop Orchards - 508 Canaan Road / Route 295, Richmond, Massachusetts 01254, 35 min ride. Voted one of the top 5 places for pick-your-own apples in MA! Their secluded location offers beautiful views of the Berkshire hills. Wine tastings are also available as Hilltop is home to the Furnace Brook Winery. They make delicious cider and the most delectable freshly made hot cider donuts.

Adventure
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