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.
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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!
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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.
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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!
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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!
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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).
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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.
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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!
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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!
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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.
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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.
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Kituo cha Ski cha Mlima wa Catamount
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!
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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.
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Monument Mountain
Popular hiking spot with beautiful, sweeping views of the Housatonic River Valley.