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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

BEST KAROAKE – The Egremont Barn

If you're looking to belt out your favorite tunes in an unforgettable atmosphere, The Egremont Barn is the place to be! With its cozy, rustic vibe and lively crowd, this venue transforms into karaoke heaven, where everyone from seasoned pros to shower-singing superstars can shine

01 review

BEST KAROAKE – The Egremont Barn

17 Main St, South Egremont, MA 01258

Nightlife Southern Berkshire County

BEST HARDWARE STORE: Carr Hardware

Carr Hardware is the ultimate destination for all your home improvement needs, blending a rich history with a modern selection of tools, supplies, and expert advice. This locally-owned gem caters to DIY enthusiasts and professionals alike, offering everything from paint and plumbing to garden

01 review

BEST HARDWARE STORE: Carr Hardware

547 North St, Pittsfield, MA 01201

Shopping Central Berkshire County

BEST PLACE TO PICK UP A COOL GIFT: Crystal Essence

Crystal Essence is your go-to destination for unique and thoughtful gifts that spark joy and inspire awe. This charming shop offers a carefully curated selection of crystals, handcrafted jewelry, and holistic wellness products that cater to all tastes and occasions. With a warm and inviting

01 review

BEST PLACE TO PICK UP A COOL GIFT: Crystal Essence

39 Railroad St, Great Barrington, MA 01230

Shopping Southern Berkshire County

BEST NURSERY & GARDEN CENTER: Ward’s Nursery & Garden Center

Ward's Nursery & Garden Center is a verdant oasis for garden enthusiasts, offering an extensive selection of plants, flowers, and gardening supplies to bring your outdoor spaces to life. With knowledgeable staff ready to provide expert advice, this local gem is dedicated to helping you

01 review

BEST NURSERY & GARDEN CENTER: Ward’s Nursery & Garden Center

Shopping Southern Berkshire County

BEST LIFE CARE COMMUNITY: Kimball Farms Life Care Community

Kimball Farms Life Care Community is a haven of comfort and support, making it the premier choice for senior living in the Berkshires. With a vibrant atmosphere, residents enjoy a full range of amenities, activities, and healthcare services tailored to their individual needs. The dedicated staff

01 review

BEST LIFE CARE COMMUNITY: Kimball Farms Life Care Community

235 Walker St, Lenox, MA 01240

Community Southern Berkshire County

BEST FUNERAL HOME: Finnerty & Stevens Funeral Home

During life’s most challenging moments, Finnerty & Stevens Funeral Home stands as a pillar of compassion and support for families in the Berkshires. Known for their respectful and personalized service, they help guide you through the process of honoring your loved one’s memory with grace and

01 review

BEST FUNERAL HOME: Finnerty & Stevens Funeral Home

426 Main St, Great Barrington, MA 01230

Community Southern Berkshire County

BEST PET SUPPLY STORE: BensDotter’s Pet

At BensDotter's Pet, your furry friends are treated like family, making it the top choice for pet lovers in the Berkshires. This charming pet store offers a wide array of high-quality pet supplies, gourmet treats, and unique toys to keep your pets happy and healthy. With a team of knowledgeable

01 review

BEST PET SUPPLY STORE: BensDotter’s Pet

940 Main St, Great Barrington, MA 01230

Shopping Southern Berkshire County

BEST FLORIST: Wildflowers Florist

When it comes to stunning arrangements that capture the essence of nature, Wildflowers Florist is your go-to destination. Known for their artistry and creativity, they craft breathtaking floral designs for every occasion, from weddings to birthdays and everything in between. With a commitment to

01 review

BEST FLORIST: Wildflowers Florist

490 Main St, Great Barrington, MA 01230

Shopping Southern Berkshire County

BEST CREDIT UNION: Greylock Federal Credit Union

Greylock Federal Credit Union redefines what it means to bank locally with personalized service and a dedication to community-driven values. More than just a place to keep your money, Greylock offers everything from checking and savings accounts to home loans, auto financing, and investment

01 review

BEST CREDIT UNION: Greylock Federal Credit Union

150 West Street Pittsfield, MA 01201

Community Central Berkshire County

BEST AUTO REPAIR: Apex Automotive

When your vehicle needs expert care, Apex Automotive rises above the rest. Known for their precision, honesty, and top-notch service, Apex is the place you trust to keep your car running smoothly. Whether it’s routine maintenance or complex repairs, the skilled team here approaches every job with

01 review

BEST AUTO REPAIR: Apex Automotive

9 Crissey Rd, Great Barrington, MA 01230

Community Southern Berkshire County

BEST GOLF COURSE: Wyantenuck Country Club

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

01 review

BEST GOLF COURSE: Wyantenuck Country Club

46 W Sheffield Rd, Great Barrington, MA 01230

Community Southern Berkshire County

BEST BURGER & FRIES: The Bistro Box

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

01 review

BEST BURGER & FRIES: The Bistro Box

937 S Main St, Great Barrington, MA 01230

Dining Southern Berkshire County

BEST COMMUNITY HUB: Berkshire South Community Center

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

01 review

BEST COMMUNITY HUB: Berkshire South Community Center

15 Crissey Rd, Great Barrington, MA 01230

Community Southern Berkshire County

BEST CULTURAL VENUE: Tanglewood

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

01 review

BEST CULTURAL VENUE: Tanglewood

297 West St, Lenox, MA 01240

Arts & Culture Southern Berkshire County

BEST FINE DINING EXPERIENCE: Cafe Adam

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

01 review

BEST FINE DINING EXPERIENCE: Cafe Adam

420 Stockbridge Rd, Great Barrington, MA 01230

Dining Southern Berkshire County

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BEST PLACE TO BUY SHOES AND BOOTS: Barrington Outfitters

Step into style and comfort at Barrington Outfitters, the premier destination for shoes and boots in the Berkshires. Whether you're hiking the trails, hitting the town, or looking for everyday comfort, Barrington Outfitters has you covered with an impressive selection of top-quality brands and

01 review

BEST PLACE TO BUY SHOES AND BOOTS: Barrington Outfitters

289 Main St, Great Barrington, MA 01230

Shopping Southern Berkshire County

BEST POOL SERVICE: Leisure Pools Service

When it comes to keeping your pool pristine and summer-ready, Leisure Pools Service has you covered. Whether it's routine cleaning, equipment repair, or a complete renovation, their team of experts ensures your pool remains a sparkling oasis. With top-notch customer service and attention to

01 review

BEST POOL SERVICE: Leisure Pools Service

1418 Canaan Southfield Rd, Southfield, MA 01259

Home & Design Southern Berkshire County

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 COFFEE & COMMUNITY VIBE: Six Depot Roastery & Café

For coffee lovers and community seekers alike, Six Depot Roastery & Café in West Stockbridge is a hidden gem in the Berkshires. With their small-batch, artisan-roasted coffee and cozy café atmosphere, this spot is the perfect place to sip and relax. Offering everything from espresso classics

01 review

BEST COFFEE & COMMUNITY VIBE: Six Depot Roastery & Café

6 Depot Street, West Stockbridge, MA 01266

Dining Southern Berkshire County

BEST BOOK NEST: The Bookloft

Step into The Bookloft, where every corner whispers stories waiting to be discovered. This cozy haven for bibliophiles is more than just a bookstore; it’s a sanctuary for the imagination. With shelves brimming with everything from bestsellers to hidden gems, you’ll find the perfect read for every

01 review

BEST BOOK NEST: The Bookloft

63 State Rd, Great Barrington, MA 01230

Shopping Southern Berkshire County

BEST CANNABIS DISCOUNTS: Theory Wellness

Theory Wellness in Great Barrington is the go-to spot for cannabis enthusiasts looking for exceptional quality and unbeatable discounts. This vibrant dispensary offers a wide selection of top-tier products, from premium flower to edibles and concentrates, all at prices that won’t break the bank.

01 review

BEST CANNABIS DISCOUNTS: Theory Wellness

1130 State Road, Great Barrington, MA 01230

Shopping 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 BOTTLES OF JOY: SPIRITED Wines

SPIRITED Wines in Lenox is where wine lovers find their happy place. With an impressive selection of meticulously curated wines from around the globe, this charming shop is perfect for both seasoned connoisseurs and casual sippers. The knowledgeable staff is eager to share their expertise, guiding

01 review

BEST BOTTLES OF JOY: SPIRITED Wines

444 Pittsfield Rd, Lenox, MA 01240

Shopping Southern Berkshire County

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BEST GREAT BARRINGTON MEET UP: The Well

BEST GREAT BARRINGTON MEET UP: The Well

BEST GREAT BARRINGTON MEET UP: The Well

BEST KAROAKE – The Egremont Barn

BEST KAROAKE – The Egremont Barn

BEST KAROAKE – The Egremont Barn

BEST HARDWARE STORE: Carr Hardware

BEST HARDWARE STORE: Carr Hardware

BEST HARDWARE STORE: Carr Hardware

BEST PLACE TO PICK UP A COOL GIFT: Crystal Essence

BEST PLACE TO PICK UP A COOL GIFT: Crystal Essence

BEST PLACE TO PICK UP A COOL GIFT: Crystal Essence

BEST NURSERY & GARDEN CENTER: Ward’s Nursery & Garden Center

BEST NURSERY & GARDEN CENTER: Ward’s Nursery & Garden Center

BEST NURSERY & GARDEN CENTER: Ward’s Nursery & Garden Center

BEST LIFE CARE COMMUNITY: Kimball Farms Life Care Community

BEST LIFE CARE COMMUNITY: Kimball Farms Life Care Community

BEST LIFE CARE COMMUNITY: Kimball Farms Life Care Community

BEST FUNERAL HOME: Finnerty & Stevens Funeral Home

BEST FUNERAL HOME: Finnerty & Stevens Funeral Home

BEST FUNERAL HOME: Finnerty & Stevens Funeral Home

BEST PET SUPPLY STORE: BensDotter’s Pet

BEST PET SUPPLY STORE: BensDotter’s Pet

BEST PET SUPPLY STORE: BensDotter’s Pet

BEST FLORIST: Wildflowers Florist

BEST FLORIST: Wildflowers Florist

BEST FLORIST: Wildflowers Florist

BEST CREDIT UNION: Greylock Federal Credit Union

BEST CREDIT UNION: Greylock Federal Credit Union

BEST CREDIT UNION: Greylock Federal Credit Union

BEST AUTO REPAIR: Apex Automotive

BEST AUTO REPAIR: Apex Automotive

BEST AUTO REPAIR: Apex Automotive

BEST GOLF COURSE: Wyantenuck Country Club

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 BURGER & FRIES: The Bistro Box

BEST COMMUNITY HUB: Berkshire South Community Center

BEST COMMUNITY HUB: Berkshire South Community Center

BEST COMMUNITY HUB: Berkshire South Community Center

BEST CULTURAL VENUE: Tanglewood

BEST CULTURAL VENUE: Tanglewood

BEST CULTURAL VENUE: Tanglewood

BEST FINE DINING EXPERIENCE: Cafe Adam

BEST FINE DINING EXPERIENCE: Cafe Adam

BEST FINE DINING EXPERIENCE: Cafe Adam

Load more

Suggested Listings

Keep exploring...

BEST PLACE TO BUY SHOES AND BOOTS: Barrington Outfitters

BEST PLACE TO BUY SHOES AND BOOTS: Barrington Outfitters

BEST PLACE TO BUY SHOES AND BOOTS: Barrington Outfitters

BEST POOL SERVICE: Leisure Pools Service

BEST POOL SERVICE: Leisure Pools Service

BEST POOL SERVICE: Leisure Pools Service

BEST LOCAL DANCE COMPANY: Berkshire Pulse

BEST LOCAL DANCE COMPANY: Berkshire Pulse

BEST LOCAL DANCE COMPANY: Berkshire Pulse

BEST COFFEE & COMMUNITY VIBE: Six Depot Roastery & Café

BEST COFFEE & COMMUNITY VIBE: Six Depot Roastery & Café

BEST COFFEE & COMMUNITY VIBE: Six Depot Roastery & Café

BEST BOOK NEST: The Bookloft

BEST BOOK NEST: The Bookloft

BEST BOOK NEST: The Bookloft

BEST CANNABIS DISCOUNTS: Theory Wellness

BEST CANNABIS DISCOUNTS: Theory Wellness

BEST CANNABIS DISCOUNTS: Theory Wellness

BEST JEWELER: Zabian’s Fine Jewelers

BEST JEWELER: Zabian’s Fine Jewelers

BEST JEWELER: Zabian’s Fine Jewelers

BEST BOTTLES OF JOY: SPIRITED Wines

BEST BOTTLES OF JOY: SPIRITED Wines