Guidebook: Berkshires Country Retreat
My favorite dinner spots
Delicious new American, farm-to-table cuisine set in a gorgeous updated farmhouse, less than a ten-minute drive from the house. There's a patio and firepit perfect for outdoor dining/cocktails.
99 locals recommend
John Andrews
224 Hillsdale RdDelicious new American, farm-to-table cuisine set in a gorgeous updated farmhouse, less than a ten-minute drive from the house. There's a patio and firepit perfect for outdoor dining/cocktails.
Great local pizza spot right in the heart of downtown Great Barrington. Perfect for dine-in or takeout!
121 locals recommend
Baba Louie's Sourdough Pizza
42/44 Railroad StGreat local pizza spot right in the heart of downtown Great Barrington. Perfect for dine-in or takeout!
Elevated American cuisine set in a 1700s-era refurbished grist mill. Less than a ten-minute drive from the house, Old Mill has an elegant, yet rustic atmosphere with great food and drinks.
75 locals recommend
Old Mill
53 Main StElevated American cuisine set in a 1700s-era refurbished grist mill. Less than a ten-minute drive from the house, Old Mill has an elegant, yet rustic atmosphere with great food and drinks.
A warm and inviting local steakhouse with great food and cocktails. Located in downtown Great Barrington, this is probably our most frequented restaurant!
7 locals recommend
Number Ten
10 Castle StreetA warm and inviting local steakhouse with great food and cocktails. Located in downtown Great Barrington, this is probably our most frequented restaurant!
My favorite breakfast & lunch spots
A quaint and toasty local cafe -- a great spot for breakfast, brunch, or lunch!
21 locals recommend
Pleasant and Main Cafe General Store
1063 Main StA quaint and toasty local cafe -- a great spot for breakfast, brunch, or lunch!
The best sandwiches and burgers in town! There can be a long line on the weekends, but I promise it's worth it! Note that this a roadside eatery with plenty of outdoor seating (no indoor dining available).
47 locals recommend
The Bistro Box
937 S Main StThe best sandwiches and burgers in town! There can be a long line on the weekends, but I promise it's worth it! Note that this a roadside eatery with plenty of outdoor seating (no indoor dining available).
Great local towns
Adorable local town that's the perfect spot to spend an afternoon/evening, featuring a walkable downtown with lots of shopping and restaurants.
86 locals recommend
Lenox
Adorable local town that's the perfect spot to spend an afternoon/evening, featuring a walkable downtown with lots of shopping and restaurants.
Lively downtown area with shopping and restaurants. Only ten minutes from the house!
188 locals recommend
Great Barrington
Lively downtown area with shopping and restaurants. Only ten minutes from the house!
Fun things to do and see
Perfect place to spend a fall afternoon! Apple picking is the big draw, but they also have wine tasting and a little cafe/shop with amazing apple cider donuts and other items for sale. The setting is also gorgeous -- views from the orchards are incredible!
41 locals recommend
Hilltop Orchards Home of Furnace Brook Winery
508 Canaan RdPerfect place to spend a fall afternoon! Apple picking is the big draw, but they also have wine tasting and a little cafe/shop with amazing apple cider donuts and other items for sale. The setting is also gorgeous -- views from the orchards are incredible!
One of our absolute favorite local spots. Enjoy a flight of wine, live music, and beautiful views! Perfect for groups.
29 locals recommend
Balderdash Cellars
81 State RdOne of our absolute favorite local spots. Enjoy a flight of wine, live music, and beautiful views! Perfect for groups.
A family-friendly ski resort that's only a ten-minute drive from the house! Known as one of the best mid-sized ski areas on the East coast.
329 locals recommend
Catamount Mountain Ski Resort
78 Catamount RdA family-friendly ski resort that's only a ten-minute drive from the house! Known as one of the best mid-sized ski areas on the East coast.
Great local spot for live music and drinks. Less than a ten-minute drive from the house!
50 locals recommend
The Barn
17 Main StGreat local spot for live music and drinks. Less than a ten-minute drive from the house!
Popular hiking spot with beautiful, sweeping views of the Housatonic River Valley.
53 locals recommend
Monument Mountain
Popular hiking spot with beautiful, sweeping views of the Housatonic River Valley.