It would be really difficult to run out of places to eat and drink in the Berkshires and especially around Great Barrington. The below list isn't exhaustive but are some of our favorite places to go. We are downright regulars at a couple of them.

Breakfast + Lunch (Sometimes Dinner)

• Marjoram + Roux 
• The Great Barrington Bagel Co.& Deli Recommend ordering ahead on their website and picking up. This is an extremely popular breakfast spot, and waits can be as long as 30 minutes for a bagel sandwich
• Fuel Bistro & Coffee Coffee, pastries, sandwiches, salads, soups
• Bear Butter Smoothies and acai bowls
• Bistro Box (Seasonal) DO NOT MISS!!! If they are open you must go!
• Rubiners Cheesemongers + Rubi's Cafe (down the alley) - Get all the makings of an epic cheese board or a grilled cheese like no other down the alley at Rubis
• The Southfield Store This is a great stop heading back towards NYC or out on an adventure as its about 20 minutes from the house, but the coffee is strong, pastries are flaky, and the food is delicious. 
• Roberto's Pizza Located in the quaint town of Sheffield 
• Manhattan Pizza
• Juju's! Popcorn chicken + cauliflower, great salads and yummy soft serve ice cream

Dinner (+Lunch)

• Fiddleheads Grille Really close to the house and where the locals eat. Good food, nothing fussy.
• The Pub New place owned by Roberto's Pizza in Sheffield
• cafeADAM Fine dining, locally sourced and grown ingredients. Worth a visit, if you can get a reservation
• Prairie Whale Foodies rejoice and sip a cocktail while you play cornhole and wait for your table
• No. 10 Classic steakhouse. great bar and really large whisky selection
• The Elm Great cocktails, oysters and burgers. Swanky and fun vibe.
• The Well Elevated pub food, friendly accommodating staff, TVs to watch the game
• GB Eats Elevated diner menu, very family friendly.
• Aegean Breeze Mediterreanean and Greek cuisine. They have vegan, vegetarian and gluten free options. 
• Bizen Japanese Restaurant & Sushi Bar
• Xicohtencatl Mexican Restaurant Upscale mexican cuisine with extensive tequila selection

Places to Sip + Sometimes Snack

• The Miller Small sports bar with a limited menu of bar snacks
• Big Elm Brewery Taprooms in Sheffield and Great Barrington, serving beer and hard seltzer
• Barrington Brewery & Restaurant The beer is brewed using solar power!
• Berkshire Mountain Distillers Small batch craft spirits
• Les Trois Emme Winery
• Moon Cloud Inventive yummy cocktails, pickled veggie boards and salumi. Don't miss the blue fish dip
• Lucys Rendezvous Looking for late night, Lucy's might be your spot

Sweets

• SoCo Creamery
• Modern Milk Bar
• Robin's Candy
• Patisserie Lenox
• JuJu's!

Farmers Markets

• Great Barrington Farmers Market:  Every Saturday 9a-1p May-November ✨ service pets only 🐕‍🦺18 Church Street
• Sheffield Farmers Market:  Kick-off May 23rd, Fridays from 3:00 pm- 6:00 pm in the Old Parish Church parking lot (125 Main Street, Sheffield, MA 01257). 
•  Farmers' Markets in the Berkshires 
•  Berkshire Farmers Markets | Fresh Food & Community 

Grocery 

• Big Y: within 5 minutes, full pharmacy, sushi, pizza, bakery, wine + liquor store closes at 9pm. There is a Big Y store card on a key ring on the hooks in the hallway
• Guidos: Upscale market with hot bar, burrito bar, florist, kitchenware store, wine + liquor, cheese shop
• Berkshire Food Co-Op: Located in downtown Great Barrington with a hot bar, cafe and groceries

Hiking

• Appalachian Trail, go right out of the driveway (about a 1000 ft) look for the trail marker 
• Great Barrington, Massachusetts Trails & Trail Maps | TrailLink 
• 10 Best trails and hikes in Great Barrington | AllTrails 
• The best Hiking in and near Great Barrington, Massachusetts 
• From Lakeside to Mountaintop: 15 Great Barrington's Hiking Spectrum - Thebostondaybook.com
• Hiking Trustees properties

Biking

•  Great Barrington, Massachusetts Trails & Trail Maps | TrailLink 
•  Great Barrington, Massachusetts Mountain Biking Trails | Trailforks 
•  Thunder Mountain Bike Park - Berkshire East Mountain Resort 

Fishing

•  Fly Fishing Trips & Lessons in the Berkshires, MA 
•  Fishing around Great Barrington, MA 
• Three Mile Pond

Kayaking + Canoeing

• Benedict Pond Boat Launch
• Housatonic River Access - Brookside Road
• Housatonic River Access - Division Street
• Housatonic River Access - East Sheffield Road
• Housatonic River Access - Covered Bridge Lane
• Lake Mansfield Boat Launch
• Three Mile Pond

Swimming

• Lake Mansfield Park

Zipline + Adventure Park

• Catamount Zipline Tour
• Aerial Adventure Park
• Scenic Chair Lift Rides

Skiing

• SkiButternut
• Catamount Mountain Resort
• Berkshire East

Whitewater Rafting

• Zoar Outdoor

Playground

• Giggle Park  located behind Great Barrington Town Hall

Farm Visit

• High Lawn located in Lee get homemade ice cream, cheese, butter and maybe even pet some real cows

• Mahaiwe Performing Arts Center
• The Barn
• Tanglewood
• Mass MoCA
• Guthrie Center & Foundation
• The Lions Den

• W.E.B. Du Bois National Historic Site - Great Barrington, MA
• Mass MoCa - North Adams, MA
• Norman Rockwell Museum - Stockbridge, MA
• Naumkeag - Stockbridge, MA
• The Mount, Edith Wharton's estate - Lenox, MA
• Hancock Shaker Village - Pittsfield, MA
• Ventfort Hall - Lenox, MA

• Thirsty Cat Festival (July) - Catamount Mountain Resort
• Berkshire Arts Festival (July 4-6) - Ski Butternut
• Daffodil and Tulip Festival (April-May)- Naumkeg

• Shopping on Main Streat, Great Barrington
• Cove Bowling & Entertainment
• The Triplex Cinema
• Guthrie Center & Foundation
• Asia Barong
• And All That Jazz Antiques

•  Great Barrington, MA Travel Guide: The Most Charming Town in the Berkshires | Vogue 
•  36 Hours in the Berkshires, Massachusetts: Things to Do and See - The New York Times 
•  Celebrating the Berkshires’ Housatonic River - The New York Times 
•  The Berkshires: A Weekend of Things to Do | The Strategist