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BEST NEIGHBORHOOD: Great Barrington

Great Barrington is the epitome of charming small-town living, where vibrant community spirit and stunning landscapes come together in perfect harmony. Known for its friendly atmosphere, this neighborhood is brimming with delightful shops, cozy cafes, and cultural attractions that make it a joy to

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Community Southern Berkshire County

BEST PUBLIC VIEW: Olivia’s Overlook

1660 Stockbridge Road, Great Barrington, MA 01230

Perched high above the rolling hills of the Berkshires, Olivia's Overlook offers a breathtaking panorama that simply takes your breath away. This hidden gem is the perfect spot to soak in the beauty of the changing seasons, whether it's the vibrant colors of fall or the lush greenery of summer

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Community Southern Berkshire County

BEST PLACE TO TAKE A WALK: Beartown Mountain

525 Beartown Mountain Road, Monterey, MA 01245

If you’re looking for a slice of nature that feels like it was made just for wandering, Beartown Mountain is your go-to spot. With its lush trails winding through towering trees and scenic vistas, every step here feels like an invitation to explore. Whether you’re hiking solo or enjoying a stroll

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Community Southern Berkshire County

Suggested Listings

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BEST BREWS & BITES: Barrington Brewery & Restaurant

424 Stockbridge Road, Great Barrington, MA 01230

For the perfect pairing of craft beer and delicious food, Barrington Brewery & Restaurant in Great Barrington is the place to be! Known for their fresh, small-batch brews made on-site, this local favorite serves up everything from rich stouts to crisp lagers, perfect for any palate

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Dining 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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Arts & Culture Southern Berkshire County

BEST BUILDING MATERIALS: Dresser-Hull Lumber & Building Supply

Dresser-Hull Lumber & Building Supply stands out as the premier destination for quality building materials in the Berkshires. With a vast selection of lumber, hardware, and tools, this local gem caters to both seasoned contractors and DIY enthusiasts alike. Their knowledgeable staff provides

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Home & Design Southern Berkshire County

BEST CATINA – Jalisco Cantina

85 Main St, Lee, MA 01238

Jalisco Cantina is the best spot to experience authentic Mexican flavors with a modern twist. Known for its vibrant atmosphere and expertly crafted dishes, this local favorite serves up everything from mouthwatering tacos and enchiladas to flavorful salsas and house-made guacamole

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Dining Central Berkshire County

BEST PITTSFIELD MEET UP: Methuselah Bar and Lounge

391 North St, Pittsfield, MA 01201

Looking for the perfect spot to meet up with friends or spark some spontaneous conversation with the coolest crowd in Pittsfield? Methuselah Bar and Lounge is the place. With its sleek, modern vibe, an ever-rotating craft beer list, and carefully curated wine and cocktail selections, it’s where

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Nightlife 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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Dining Southern Berkshire County

BEST COZY BAR: Common or Garden Pub

425 Park St, Great Barrington, MA 01230

When the chill of Berkshire evenings sets in, there’s no better place to find warmth and camaraderie than the Common or Garden Pub. This charming spot is a hidden gem, boasting a welcoming atmosphere with its rustic decor and soft lighting. Sip on a craft cocktail or a local brew while curling up

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Dining Southern Berkshire County

BEST FOREIGN AUTO REPAIR: AutoBahn Services

1851 N Main St, Sheffield, MA 01257

When it comes to foreign auto repair, Autobahn Services stands out for its expertise and commitment to quality. Specializing in luxury brands like BMW, Audi, and Mercedes-Benz, their skilled technicians provide exceptional care tailored to each vehicle's needs. With a focus on transparency and

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Community Southern Berkshire County

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What do you need?

BEST NEIGHBORHOOD: Great Barrington

BEST NEIGHBORHOOD: Great Barrington

BEST PUBLIC VIEW: Olivia’s Overlook

BEST PUBLIC VIEW: Olivia’s Overlook

BEST PLACE TO TAKE A WALK: Beartown Mountain

BEST PLACE TO TAKE A WALK: Beartown Mountain

Suggested Listings

Keep exploring...

BEST BREWS & BITES: Barrington Brewery & Restaurant

BEST BREWS & BITES: Barrington Brewery & Restaurant

BEST CULTURAL VENUE: Tanglewood

BEST CULTURAL VENUE: Tanglewood

BEST BUILDING MATERIALS: Dresser-Hull Lumber & Building Supply

BEST BUILDING MATERIALS: Dresser-Hull Lumber & Building Supply

BEST CATINA – Jalisco Cantina

BEST CATINA – Jalisco Cantina

BEST PITTSFIELD MEET UP: Methuselah Bar and Lounge

BEST PITTSFIELD MEET UP: Methuselah Bar and Lounge

BEST FINE DINING EXPERIENCE: Cafe Adam

BEST FINE DINING EXPERIENCE: Cafe Adam

BEST COZY BAR: Common or Garden Pub

BEST COZY BAR: Common or Garden Pub

BEST FOREIGN AUTO REPAIR: AutoBahn Services

BEST FOREIGN AUTO REPAIR: AutoBahn Services