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  • 36 acres of land with 2 hiking trails and an outdoor fire pit
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Background of wine on shelves with bottle and goblet of wine and grape bunches in foreground

Sip and Swirl Your Way Through 5 Great Berkshires Wineries

Save yourselves a trip to California and come sip and swirl your way through 5 great Berkshires wineries. Located within a 15- to 35-minute drive of our bed and breakfast in the Berkshires, these 5 lovely wineries offer an exceptional way to spend an afternoon exploring new wines and gorgeous scenery. Let us pack you a gourmet picnic basket to enjoy as you travel from place to place. And be sure to choose a designated driver for the afternoon’s vino adventure.

1. Balderdash Cellars

81 State Road, Richmond, Massachusetts 01254 | (413) 464-4629

Founded in 2011, Balderdash Cellars prides itself on producing great vintages from imported world-class California grapes. With whimsical names like Liar’s Bench, Joyride, and Truth Serum, the wines they produce all have a backstory. Their tagline, “wicked wines & tall tales” says it all. Situated on a beautiful lake in western Massachusetts, Balderdash is more than just a winery. Sample the offerings of onsite food trucks or bring your own. Stay for the afternoon and early evening to enjoy live music often playing on weekends throughout the summer.

2. Furnace Brook Winery

508 Canaan Road, Richmond, Massachusetts 01254 | (800) 833-6274

While Hilltop Orchards is more noted for its apple cider and cider donuts, they also produce some award-winning varietals under the umbrella of Furnace Brook Winery. The orchard is a year-round destination for hiking and cross-country skiing on an amazing network of trails. And their hilltop location offers some spectacular views of the Berkshire hills and valleys. Be sure to stop at the Farm Store for yummy apple cider donuts made daily and to pick up a bottle of their latest vintage.

Hard cider and apple orchard

3. Home Range Winery

146 Flints Crossing Road, Canaan, New York 12029 | (518) 610-6821

Family-owned and operated, Home Range Winery produces handmade wines in small batches. Perched between the Hudson Valley and the western edge of the Berkshires, the wines produced here come from grapes grown onsite at their Flatbrook Farm along with their homegrown raspberries, blueberries, and blackberries. Check out their calendar of events for visiting food trucks and entertainment.

4. Hudson-Chatham Winery

1900 State Route 66, Ghent, New York 12075 | (518) 392-9463

Hailed as the first winery to find a home in Columbia County, NY, Hudson-Chatham Winery established its roots on a former dairy farm in 2006. Now owned by 2 graduates of the Culinary Institute of America, the winery produces sustainably farmed wines from hybrid grapes. Book a curated experience for a seated tasting of 6 wines accompanied by seasonal snacks prepared in the vineyard kitchen.

Cluster of green grapes on the vine

5. Les Trois Emme Vineyard & Winery

8 Knight Road, New Marlborough, Massachusetts 01230 | (413) 528-1015

Relax in the rural setting of Les Trois Emme Vineyard & Winery in New Marlborough. This peaceful spot invites you to relax in the gazebo and taste a variety of excellent wines while noshing on complimentary hors d’oeuvres or the picnic you packed. Take home a bottle of Stingy Jack’s Pumpkin Wine, a family tradition crafted from white wine infused with pumpkin spices.

An afternoon spent sipping and swirling your way through 5 great Berkshires wineries will no doubt leave you a bit tuckered out. So, wend your way back to Devonfield and take a relaxing dip in the pool, or grab an Adirondack chair and take a snooze on the lawn. Or, better yet, uncork your latest find and unwind in the comfort of your luxurious room. Once you’ve rested up, venture out for dinner at one of the best restaurants in the Berkshires.

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