Food & Drink
- Best Bakery – Bakin’ Bakery
- Best Bar – The Barn
- Best Breakfast – Great Barrington Bagel Company & Deli
- Best Burger – The Bistro Box
- Best Butcher – Mazzeo’s Meat and Seafood
- Best Coffee Shop – Fuel
- Best Distillery – Berkshire Mountain Distillers
- Best Fine Dining – John Andrews Farmhouse Restaurant
- Best Grocery Store – Guido’s Fresh Marketplace
- Best Ice Cream – SoCo Creamery
- Best International Cuisine – Aroma Bar & Grill
- Best Mexican Food – La Fiesta
- Best Organic Food – Berkshire Food Co-op
- Best Pizza – Roberto’s Pizza
- Best Restaurant – Olde Heritage Tavern
- Best Winery – Balderdash Cellars
Recreation
- Best Concert Venue – Tanglewood
- Best Fitness Gym – Berkshire South Regional Community Center
- Best Golf Course – Stockbridge Golf Club
- Best Museum – Norman Rockwell Museum
- Best Outdoor Recreation – Ski Butternut
Services
- Best Community Service Organization – Construct, Inc.
- Best Place to Work – Fairview Hospital
- Best Auto Repair – Autobahn Service
- Best Bank – Greylock Federal Credit Union
- Best Contractor – Morrison’s Home Improvement
- Best Dentist – Thomas Mullany
- Best Florist – Bella Flora
- Best Funeral Home – Finnerty & Stevens Funeral Home
- Best Hotel/Motel – Red Lion Inn
- Best Landscaping/Lawn Care – Strong Oak Landscaping
- Best Nursing Home/Retirement Community – Kimball Farms
- Best Pediatrician – MACONY Pediatric and Adolescent Medicine
- Best Physician – East Mountain Medical Clinic of BHS
- Best Real Estate Agent – Stone House Properties, LLC
- Best Salon/Barbershop – Michele’s Salon & Day Spa
- Best Veterinarian – Bilmar Veterinary Services
- Best Wealth Management – Berkshire Money Management
Shopping
- Best Car Dealer – Haddad Auto
- Best Antiques Dealer – The Emporium
- Best Bike Shop – Berkshire Bike & Board
- Best Cannabis Dispensary – Theory Wellness
- Best Consignment/Resale Shop – Catwalk Boutique
- Best Furniture Store – Paul Rich & Sons
- Best Gallery – Bernay Fine Art
- Best Garden Center – Ward’s Nursery & Garden Center
- Best Gift Shop – The Shop by Only in My Dreams Events
- Best Hardware Store – Carr Hardware
- Best Jeweler – Lennox Jewelers
- Best Men’s Clothing – Zabian’s Clothing
- Best Pet Supplies/Services – BensDotter’s Pet
- Best Pharmacy – Lenox Village Pharmacy
- Best Toy Store – Tom’s Toys
- Best Women’s Clothing – MainStreet