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BEST PLACE TO TAKE A WALK: Beartown Mountain

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

01 review

BEST PLACE TO TAKE A WALK: Beartown Mountain

525 Beartown Mountain Road, Monterey, MA 01245

Community Southern Berkshire County

BEST LOCAL TELEVISION STATION: CTSB Public Television

In the bustling heart of Lee, CTSB Public Television shines as a beacon of community storytelling and local culture. With a mission to inform, educate, and entertain, this station offers a unique blend of programming that highlights the diverse voices and talents of the Berkshires

01 review

BEST LOCAL TELEVISION STATION: CTSB Public Television

75 Park Street, Lee, MA 01238

Community Southern Berkshire County

BEST COMMUNITY RESOURCE: Mason Public Library

Tucked away in the heart of Great Barrington, Mason Public Library is not just a place for books; it's a vibrant hub of community life. Walking through its doors, you’re greeted by the warm smiles of friendly staff ready to guide you to your next great read or an engaging program.

01 review

BEST COMMUNITY RESOURCE: Mason Public Library

231 Main Street, Great Barrington, MA 01230

Community Southern Berkshire County

BEST HISTORIC RETREAT: Naumkeag

Naumkeag offers an unparalleled blend of history, beauty, and tranquility, making it the ultimate historic retreat in the Berkshires. This Gilded Age mansion and its stunning gardens, designed by renowned landscape architect Fletcher Steele, provide visitors with an immersive experience of

01 review

BEST HISTORIC RETREAT: Naumkeag

5 Prospect Hill Road, Stockbridge, MA 01262

Community Southern Berkshire County

BEST JEWELER: Zabian’s Fine Jewelers

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

01 review

BEST JEWELER: Zabian’s Fine Jewelers

15 Main St, Lee, MA 01238

Shopping Southern Berkshire County

BEST VENUE: The Mahaiwe Performing Arts Center

The Mahaiwe Performing Arts Center, located in the heart of Great Barrington, is hands down the best venue for world-class entertainment in the Berkshires. Known for its rich history and elegant, intimate setting, the Mahaiwe hosts an impressive lineup of performances, from live music and

01 review

BEST VENUE: The Mahaiwe Performing Arts Center

14 Castle St, Great Barrington, MA 01230

Arts & Culture Southern Berkshire County

BEST BOTANICAL GARDENS: Berkshire Botanical Garden

The Berkshire Botanical Garden is a lush sanctuary where nature’s beauty unfolds in every season. With its stunning array of plants, vibrant flower beds, and serene walking paths, this garden is a paradise for both novice gardeners and seasoned horticulturists. Strolling through its beautifully

01 review

BEST BOTANICAL GARDENS: Berkshire Botanical Garden

5 West Stockbridge Rd, Stockbridge, MA 01262

Community Central Berkshire County

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BEST LOCAL DANCE COMPANY: Berkshire Pulse

Berkshire Pulse is a vibrant hub for creativity and expression in the heart of our community. Known for its innovative choreography and diverse performances, Pulse brings together talented dancers of all ages and backgrounds, showcasing a wide range of styles from ballet to hip-hop. The company is

01 review

BEST LOCAL DANCE COMPANY: Berkshire Pulse

420 Park St, Housatonic, MA 01236

Arts & Culture Southern Berkshire County

BEST ARTISAN PIZZA: Roberto’s Pizza

When it comes to mouthwatering pizza in Sheffield, Roberto’s Pizza is the ultimate destination for artisan pizza lovers! Known for its delicious, hand-tossed pies and fresh ingredients, this local favorite serves up a variety of classic and creative toppings that will satisfy any craving.

01 review

BEST ARTISAN PIZZA: Roberto’s Pizza

165 Main Street, Sheffield, MA 01257

Dining Southern Berkshire County

BEST SOURDOUGH PIZZA: Baba Louie’s Sourdough Pizza

For the best sourdough pizza around, Baba Louie’s Sourdough Pizza is unmatched. Known for their handcrafted sourdough crust, every pizza is baked to perfection with a unique, tangy flavor that elevates the whole experience. Topped with fresh, locally sourced ingredients and inventive combinations

01 review

BEST SOURDOUGH PIZZA: Baba Louie’s Sourdough Pizza

42/44 Railroad St, Great Barrington, MA 01230

Dining Southern Berkshire County

BEST SLICE OF PIZZA: Manhattan Pizza Co

For the best slice of pizza in town, look no further than Manhattan Pizza Co. Known for its authentic New York-style pizza, Manhattan Pizza Co. serves up perfectly thin, crispy slices with just the right amount of cheese and sauce. Whether you're a fan of classic cheese or crave something loaded

01 review

BEST SLICE OF PIZZA: Manhattan Pizza Co

490 Main St, Great Barrington, MA 01230

Dining Southern Berkshire County

BEST ICE CREAM: High Lawn Farm

For ice cream that’s a cut above the rest, High Lawn Farm in Lee is the ultimate destination. Known for their rich, creamy flavors made from milk sourced directly from their own herd of grass-fed cows, this charming farm stand offers a delightful selection that will satisfy any sweet tooth.

01 review

BEST ICE CREAM: High Lawn Farm

535 Summer St, Lee, MA 01238

Dining Southern Berkshire County

BEST RESIDENTIAL SECURITY: Lee Audio Home and Security

Lee Audio Home and Security stands out as the premier choice for safeguarding your home and loved ones. With a focus on comprehensive security solutions, they provide cutting-edge technology and tailored systems that ensure maximum protection for your property. Their experienced team conducts

01 review

BEST RESIDENTIAL SECURITY: Lee Audio Home and Security

65 Fairview St, Lee, MA 01238

Home & Design Southern Berkshire County

BEST PIZZA DELIVERY: Vivaldi’s Pizzeria

When it comes to the best pizza delivery, Vivaldi’s Pizzeria hits all the right notes. Offering a menu of delicious, freshly made pizzas with quality ingredients and a variety of toppings, Vivaldi’s guarantees a hot and satisfying meal delivered right to your door. Whether you’re craving a classic

01 review

BEST PIZZA DELIVERY: Vivaldi’s Pizzeria

325 Stockbridge Rd #4, Great Barrington, MA 01230

Dining Southern Berkshire County

BEST GREAT BARRINGTON MEET UP: The Well

When night falls in Great Barrington, The Well is the spot where locals and visitors alike gather for a good time. Known for its cozy pub atmosphere, friendly bartenders, and an unbeatable selection of craft beers and cocktails, it’s the go-to for lively conversation and spontaneous fun.

01 review

BEST GREAT BARRINGTON MEET UP: The Well

312 Main St, Great Barrington, MA 01230

Nightlife Southern Berkshire County

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BEST PLACE TO TAKE A WALK: Beartown Mountain

BEST PLACE TO TAKE A WALK: Beartown Mountain

BEST PLACE TO TAKE A WALK: Beartown Mountain

BEST LOCAL TELEVISION STATION: CTSB Public Television

BEST LOCAL TELEVISION STATION: CTSB Public Television

BEST LOCAL TELEVISION STATION: CTSB Public Television

BEST COMMUNITY RESOURCE: Mason Public Library

BEST COMMUNITY RESOURCE: Mason Public Library

BEST COMMUNITY RESOURCE: Mason Public Library

BEST HISTORIC RETREAT: Naumkeag

BEST HISTORIC RETREAT: Naumkeag

BEST HISTORIC RETREAT: Naumkeag

BEST JEWELER: Zabian’s Fine Jewelers

BEST JEWELER: Zabian’s Fine Jewelers

BEST JEWELER: Zabian’s Fine Jewelers

BEST VENUE: The Mahaiwe Performing Arts Center

BEST VENUE: The Mahaiwe Performing Arts Center

BEST VENUE: The Mahaiwe Performing Arts Center

BEST BOTANICAL GARDENS: Berkshire Botanical Garden

BEST BOTANICAL GARDENS: Berkshire Botanical Garden

BEST BOTANICAL GARDENS: Berkshire Botanical Garden

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Suggested Listings

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BEST LOCAL DANCE COMPANY: Berkshire Pulse

BEST LOCAL DANCE COMPANY: Berkshire Pulse

BEST LOCAL DANCE COMPANY: Berkshire Pulse

BEST ARTISAN PIZZA: Roberto’s Pizza

BEST ARTISAN PIZZA: Roberto’s Pizza

BEST ARTISAN PIZZA: Roberto’s Pizza

BEST SOURDOUGH PIZZA: Baba Louie’s Sourdough Pizza

BEST SOURDOUGH PIZZA: Baba Louie’s Sourdough Pizza

BEST SOURDOUGH PIZZA: Baba Louie’s Sourdough Pizza

BEST SLICE OF PIZZA: Manhattan Pizza Co

BEST SLICE OF PIZZA: Manhattan Pizza Co

BEST SLICE OF PIZZA: Manhattan Pizza Co

BEST ICE CREAM: High Lawn Farm

BEST ICE CREAM: High Lawn Farm

BEST ICE CREAM: High Lawn Farm

BEST RESIDENTIAL SECURITY: Lee Audio Home and Security

BEST RESIDENTIAL SECURITY: Lee Audio Home and Security

BEST RESIDENTIAL SECURITY: Lee Audio Home and Security

BEST PIZZA DELIVERY: Vivaldi’s Pizzeria

BEST PIZZA DELIVERY: Vivaldi’s Pizzeria

BEST PIZZA DELIVERY: Vivaldi’s Pizzeria

BEST GREAT BARRINGTON MEET UP: The Well

BEST GREAT BARRINGTON MEET UP: The Well

BEST GREAT BARRINGTON MEET UP: The Well