Chris's Guidebook of The Berkshires
Coffee Shop
Great coffee shop in Lenox, try their lattes! Delicious and beautifully created :)
16 locals recommend
Lenox Coffee
52 Main StGreat coffee shop in Lenox, try their lattes! Delicious and beautifully created :)
This is my favorite coffee shop in the Berkshires!!!
82 locals recommend
No. Six Depot Roastery & Cafe
6 Depot StThis is my favorite coffee shop in the Berkshires!!!
Fuel Bistro/ Coffee Shop
293 Main StTunnel City Coffee
100 Spring StActivities to do with Children
Vast open space for kids to run, see animals, and beautiful scenery
161 locals recommend
Hancock Shaker Village
1843 W Housatonic StVast open space for kids to run, see animals, and beautiful scenery
Berkshire Museum
39 South StMASS MoCA
1040 Mass MoCA WayLive jazz concerts every Thursday evening in the summers. Best local skiing for kids in the winter!
115 locals recommend
Bousquet Ski Area
101 Dan Fox DrLive jazz concerts every Thursday evening in the summers. Best local skiing for kids in the winter!
Food scene
The Ostrich Room
10 Richmond Mountain RoadModern day speakeasy, great cocktails and funky atmosphere
This is a winery that you can BYOB food to! Most days provides food trucks in addition. Beautiful scenery overlooking Richmond pond!! One of my favorite spots. Also kid/dog friendly.
29 locals recommend
Balderdash Cellars
81 State RdThis is a winery that you can BYOB food to! Most days provides food trucks in addition. Beautiful scenery overlooking Richmond pond!! One of my favorite spots. Also kid/dog friendly.
Great local food market with delicious pre made foods and groceries. Fun just to browse around!
248 locals recommend
Guido's Fresh Marketplace
760 S Main StGreat local food market with delicious pre made foods and groceries. Fun just to browse around!
The Olde Heritage Tavern
12 Housatonic StLocal, fair prices, good pub food :)
Alta
34 Church StDelicious food, excellent customer service
Betty's Pizza Shack
26 Housatonic StBest takeout pizza in Lenox!
Great place to grab an after dinner cocktail or start the day there with delicious breakfast!
Ophelia’s
16 Church StreetGreat place to grab an after dinner cocktail or start the day there with delicious breakfast!
Haven
8 Franklin StYummy breakfast/brunch
Gateways Inn & Restaurant
51 Walker StExcellent brunches!
Firefly Gastropub & Catering Co.
71 Church StBistro Zinc
56 Church StBrava
65 Church StMazzeo's Ristorante
1015 South StClassic Italian food that is always on point!
This is a local favorite, ski bum spot. best wings in the Berkshires, hands down. Great beer selection and pub food. Rustic atmosphere!
39 locals recommend
Olde Forge Restaurant
125 N Main StThis is a local favorite, ski bum spot. best wings in the Berkshires, hands down. Great beer selection and pub food. Rustic atmosphere!
Patrick's Pub
26 Bank RowClassic pub food in Pittsfield
District Kitchen & Bar
40 West StCool atmosphere, good food, specialty cocktails
This is my husbands favorite take out pizza place in pittsfield, they don’t deliver, but pick up is easy.
South Street Pizza House
148 South StThis is my husbands favorite take out pizza place in pittsfield, they don’t deliver, but pick up is easy.
East Side Cafe
Another pittsfield classic pizza spots that is a must try. Only pick up available.
Jae's
1032 South StreetYummy sushi spot in Pittsfield
Wine shop and group activities
This is my wife’s BFF shop, they sell delicious hand selected wines and make the experience fun by offering wine tastings and activities!
Dare Bottleshop & Provisions
11 Housatonic StreetSightseeing
The Mount, Edith Wharton's Home
2 Plunkett StA must see, breathtaking views of the Berkshire mountains and Stockbridge bowl, a cool windy road leading up!
51 locals recommend
Olivia's Overlook
Hiking TrailsA must see, breathtaking views of the Berkshire mountains and Stockbridge bowl, a cool windy road leading up!
Mount Greylock
Tallest peak in the state of Massachusetts. Breathtaking views!
Neighborhoods
Such an awesome town to walk around, shop, and grab food! My favorite Berkshire town to visit.
188 locals recommend
Great Barrington
Such an awesome town to walk around, shop, and grab food! My favorite Berkshire town to visit.