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BEST GOLF COURSE: Wyantenuck Country Club

46 W Sheffield Rd, Great Barrington, MA 01230

Tee off at Wyantenuck Country Club, where pristine fairways and stunning Berkshire views create an exceptional golfing experience. This well-kept, private course offers a challenging layout that caters to golfers of all skill levels, with smooth greens and a beautiful, natural setting that makes

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01 review

Community Southern Berkshire County

BEST BURGER & FRIES: The Bistro Box

937 S Main St, Great Barrington, MA 01230

For a burger experience that’s nothing short of legendary, The Bistro Box in Great Barrington is the spot. Known for their juicy, handcrafted burgers and crispy, golden fries, this roadside eatery serves up classic comfort food with a gourmet twist. Whether you're craving a simple cheeseburger or

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01 review

Dining Southern Berkshire County

BEST ART IMMERSION: MASS MoCA

MASS MoCA in North Adams is more than just a museum—it's an expansive playground for contemporary art lovers. Housing some of the largest and most ambitious installations in the world, this cultural gem invites visitors to get lost in its vast galleries, interactive exhibits, and live

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01 review

Arts & Culture Northern Berkshire County

BEST COMMUNITY HUB: Berkshire South Community Center

15 Crissey Rd, Great Barrington, MA 01230

Dive into the heart of community spirit at Berkshire South Community Center, where connection, wellness, and fun come together in a vibrant atmosphere. This welcoming space offers a range of programs for all ages, from fitness classes and youth sports to cultural events and workshops

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01 review

Community Southern Berkshire County

BEST CULTURAL VENUE: Tanglewood

297 West St, Lenox, MA 01240

Experience the magic of music at Tanglewood, the crown jewel of the Berkshires and summer home to the Boston Symphony Orchestra. Set against a stunning backdrop of rolling hills and lush landscapes, this iconic venue hosts an array of world-class performances, from classical concerts to

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01 review

Arts & Culture Southern Berkshire County

BEST WINERY: Balderdash Cellars

81 State Rd, Richmond, MA 01254

Raise a glass to Balderdash Cellars, where passion for winemaking and a commitment to quality converge in every bottle. Nestled in the scenic Berkshires, this winery is known for its unique varietals and small-batch approach, allowing the team to craft exceptional wines that reflect the terroir of

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01 review

Shopping Central Berkshire County

BEST FINE DINING EXPERIENCE: Cafe Adam

420 Stockbridge Rd, Great Barrington, MA 01230

Indulge in a culinary journey at Cafe Adam, where every meal is a masterpiece crafted with passion and precision. Nestled in the heart of Great Barrington, this fine dining establishment prides itself on using seasonal ingredients sourced from local farms, ensuring a fresh and flavorful

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01 review

Dining Southern Berkshire County

BEST LOCAL FOOD MARKET: Berkshire Co-op Food Market

34 Bridge St, Great Barrington, MA 01230

Discover the heart of the Berkshires at Berkshire Co-Op Food Market, where community and quality collide to create an exceptional shopping experience. This local treasure offers a vast selection of fresh, organic produce, locally sourced meats, and artisanal goods that celebrate the region

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01 review

Shopping Southern Berkshire County

BEST MEXICAN RESTAURANT: XICOHTENCATL Mexican Restaurant

50 Stockbridge Rd, Great Barrington, MA 01230

Get ready to embark on a culinary fiesta at Xicohtencatl Mexican Restaurant, where vibrant flavors and authentic dishes transport you straight to the heart of Mexico. This culinary gem is not just a restaurant; it’s a celebration of culture, offering everything from sizzling fajitas to

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01 review

Dining Southern Berkshire County

BEST BOUTIQUE HOTEL: Doctor Sax House

35 Walker St, Lenox, MA 01240

Step into luxury at the Doctor Sax House, a boutique hotel in Lenox that combines modern elegance with historic charm. Each uniquely designed room offers a cozy retreat, complete with plush furnishings and thoughtful amenities that make you feel right at home. Guests can unwind in the beautiful

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01 review

Community Southern Berkshire County

BEST HIDDEN GEM: Dulu Cafe & Lounge

35 Walker St, Lenox, MA 01240

Nestled in the historic Doctor Sax House in Lenox, Dulu Cafe & Lounge is a hidden gem that beckons food lovers and social butterflies alike. This charming café blends a cozy atmosphere with an eclectic menu that features everything from artisanal coffees to creative cocktails. Whether you’re

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01 review

Dining Southern Berkshire County

BEST CULINARY ESCAPE: Heirloom Lodge

286 Great Barrington Road, West Stockbridge, MA 01266

Heirloom Lodge in West Stockbridge offers a culinary escape that immerses you in the essence of farm-to-table dining. Each dish is crafted with care, highlighting the freshest local ingredients and seasonal flavors that reflect the Berkshire region’s bounty. The cozy, rustic atmosphere invites you

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01 review

Dining Southern Berkshire County

BEST PIZZA EXPERIENCE: Pizzeria Boema

84 Main St, Lenox, MA 01240

At Pizzeria Boema in Lenox, they take the art of ‘za to a whole new level. Pronounced {bow-em-ah}, this local treasure believes that pizza is an essential human need, and they’re on a mission to fulfill your pizza destinies, one delicious pie at a time. The atmosphere is as important as the food

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01 review

Dining Southern Berkshire County

BEST FRENCH-BERKSHIRE FUSION: The Lost Lamb

31 Main St, Stockbridge, MA 01262

The Lost Lamb in Stockbridge is a delightful patisserie that perfectly blends French culinary artistry with Berkshire charm. This cozy gem offers an array of exquisite pastries, artisan breads, and delightful treats that showcase the best of both worlds. Whether you're savoring a flaky croissant

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01 review

Dining Southern Berkshire County

BEST SCOOPS OF DELIGHT: SoCo Creamery

5 Railroad St, Great Barrington, MA 01230

SoCo Creamery in Great Barrington is the ultimate destination for ice cream lovers seeking artisanal flavors that delight the palate. This charming shop offers a rotating selection of homemade ice cream made with locally sourced ingredients, ensuring every scoop is fresh and bursting with flavor

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01 review

Dining Southern Berkshire County

BEST CANNABIS CUSTOMER SERVICE: The Pass

1375 N Main St, Sheffield, MA 01257

The Pass in Sheffield sets the gold standard for customer service in the cannabis industry. From the moment you walk in, you’re greeted by a friendly and knowledgeable staff dedicated to making your experience exceptional. Whether you're a seasoned user or a curious newcomer, the team at The Pass

5.0

01 review

Shopping Southern Berkshire County

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BEST HISTORIC MUSEUM – Venfort Hall Mansion and Gilded Age Museum

104 Walker St, Lenox, MA 01240

Step into the elegance of a bygone era at Venfort Hall, where history comes alive within its grand walls. This stunning Gilded Age mansion offers a glimpse into the opulent lifestyles of the past, with beautifully restored rooms, fascinating exhibits, and engaging tours that tell the story of the

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01 review

Arts & Culture Southern Berkshire County

BEST PROPANE SERVICE: Carlson Propane

79 Pike Rd, Sheffield, MA 01257

When it comes to reliable propane service in Sheffield, Carlson Propane stands out as the trusted choice for residential and commercial needs. Known for their exceptional customer service and timely deliveries, Carlson Propane ensures that homes and businesses stay warm and powered year

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Home & Design Southern Berkshire County

BEST LOCAL EVENT SPACE: Egremont Barn

17 Main St, South Egremont, MA 01258

For a unique and charming venue that embodies the spirit of the Berkshires, look no further than Egremont Barn! This beautifully restored barn serves as a versatile space for events ranging from weddings and parties to community gatherings and concerts. With its rustic elegance and inviting

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01 review

Nightlife Southern Berkshire County

BEST COCKTAILS: Thistle & Mirth

44 West St, Pittsfield, MA 01201

If you’re on the hunt for the finest cocktails in the Berkshires, look no further than Thistle & Mirth. Known for its creative concoctions and perfectly balanced drinks, this cozy Pittsfield bar offers an eclectic mix of handcrafted cocktails that will tantalize your taste buds.

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Nightlife Central Berkshire County

BEST JEWELER: Zabian’s Fine Jewelers

15 Main St, Lee, MA 01238

Discover the unparalleled charm of Zabian's Jeweler, the premier destination for exquisite jewelry in Berkshire County. With a rich legacy of craftsmanship and an eye for detail, Zabian's offers a stunning selection of custom designs, engagement rings, and timeless pieces that cater to every

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Shopping Southern Berkshire County

BEST DINING EXPERIENCE: Jae’s at The Hilton Garden Inn

1032 South St, Pittsfield, MA 01201

Jae's at The Hilton Garden Inn in Pittsfield offers a dining experience that seamlessly blends elegance and comfort. With a menu showcasing both classic and innovative dishes, this restaurant caters to every palate, featuring mouthwatering steaks and fresh seafood. The welcoming atmosphere and

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01 review

Dining Central Berkshire County

BEST COZY INDULGENCE: Fluff Alpaca

319 Main St, Great Barrington, MA 01230

Fluff Alpaca in Great Barrington is your go-to destination for luxurious, warm, and ultra-soft alpaca products. This boutique offers everything from cozy sweaters to stylish scarves, all made from the finest alpaca fibers that are lightweight, hypoallergenic, and irresistibly soft

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Shopping Southern Berkshire County

BEST AERIAL ADVENTURE: Catamount Aerial Adventure Park

17 Catamount Rd, South Egremont, MA 01258

Tucked beneath the lush canopy at the base of Catamount’s ski area lies an outdoor adventure unlike any other—the Catamount Aerial Adventure Park, one of the largest aerial parks in all of New England. Offering nine courses of varying difficulty, this park delivers thrills for everyone, from

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01 review

Community Southern Berkshire County

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BEST GOLF COURSE: Wyantenuck Country Club

BEST GOLF COURSE: Wyantenuck Country Club

BEST BURGER & FRIES: The Bistro Box

BEST BURGER & FRIES: The Bistro Box

BEST ART IMMERSION: MASS MoCA

BEST ART IMMERSION: MASS MoCA

BEST COMMUNITY HUB: Berkshire South Community Center

BEST COMMUNITY HUB: Berkshire South Community Center

BEST CULTURAL VENUE: Tanglewood

BEST CULTURAL VENUE: Tanglewood

BEST WINERY: Balderdash Cellars

BEST WINERY: Balderdash Cellars

BEST FINE DINING EXPERIENCE: Cafe Adam

BEST FINE DINING EXPERIENCE: Cafe Adam

BEST LOCAL FOOD MARKET: Berkshire Co-op Food Market

BEST LOCAL FOOD MARKET: Berkshire Co-op Food Market

BEST MEXICAN RESTAURANT: XICOHTENCATL Mexican Restaurant

BEST MEXICAN RESTAURANT: XICOHTENCATL Mexican Restaurant

BEST BOUTIQUE HOTEL: Doctor Sax House

BEST BOUTIQUE HOTEL: Doctor Sax House

BEST HIDDEN GEM: Dulu Cafe & Lounge

BEST HIDDEN GEM: Dulu Cafe & Lounge

BEST CULINARY ESCAPE: Heirloom Lodge

BEST CULINARY ESCAPE: Heirloom Lodge

BEST PIZZA EXPERIENCE: Pizzeria Boema

BEST PIZZA EXPERIENCE: Pizzeria Boema

BEST FRENCH-BERKSHIRE FUSION: The Lost Lamb

BEST FRENCH-BERKSHIRE FUSION: The Lost Lamb

BEST SCOOPS OF DELIGHT: SoCo Creamery

BEST SCOOPS OF DELIGHT: SoCo Creamery

BEST CANNABIS CUSTOMER SERVICE: The Pass

BEST CANNABIS CUSTOMER SERVICE: The Pass

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Suggested Listings

Keep exploring...

BEST HISTORIC MUSEUM – Venfort Hall Mansion and Gilded Age Museum

BEST HISTORIC MUSEUM – Venfort Hall Mansion and Gilded Age Museum

BEST PROPANE SERVICE: Carlson Propane

BEST PROPANE SERVICE: Carlson Propane

BEST LOCAL EVENT SPACE: Egremont Barn

BEST LOCAL EVENT SPACE: Egremont Barn

BEST COCKTAILS: Thistle & Mirth

BEST COCKTAILS: Thistle & Mirth

BEST JEWELER: Zabian’s Fine Jewelers

BEST JEWELER: Zabian’s Fine Jewelers

BEST DINING EXPERIENCE: Jae’s at The Hilton Garden Inn

BEST DINING EXPERIENCE: Jae’s at The Hilton Garden Inn

BEST COZY INDULGENCE: Fluff Alpaca

BEST COZY INDULGENCE: Fluff Alpaca

BEST AERIAL ADVENTURE: Catamount Aerial Adventure Park

BEST AERIAL ADVENTURE: Catamount Aerial Adventure Park