Food & Drink
- Best Bakery – Pixie Boulangerie
- Best Bar – Mooncloud
- Best Breakfast – GB Eats
- Best Brewery/Distillery – Barrington Brewery & Restaurant
- Best Burger – The Bistro Box
- Best Butcher – Mazzeo’s Meat and Seafood
- Best Coffee Shop – Fuel Bistro
- Best Fine Dining – Cafe Adam
- Best Grocery Store – Guido’s Fresh Marketplace
- Best Ice Cream – SoCo Creamery
- Best International Cuisine – Aroma Bar & Grill
- Best Liquor Store – Domaney’s Liquors and Fine Wines
- Best Mexican Food – Xicohtencatl
- Best Organic Food – Berkshire Food Co-op
- Best Pizza – Roberto’s Pizza
- Best Restaurant – Salmon Run Fish House
- Best Winery – Balderdash Cellars
Recreation
- Best Concert Venue – Mahaiwe Performing Arts Center
- Best Fitness Gym – Berkshire South Regional Community Center
- Best Golf Course – Wyantenuck Country Club
- Best Museum – Norman Rockwell Museum
- Best Outdoor Recreation – Catamount Ski Resort
Services
- Best Auto Repair – Autobahn Service
- Best Bank – Greylock Federal Credit Union
- Best Community Service Organization – Railroad Street Youth Project
- Best Contractor – Morrison’s Home Improvement
- Best Dentist – Jonathan J. Nacht DMD
- Best Event Planner – Only In My Dreams
- Best Florist – Township Four Floristry & Home
- Best Funeral Home – Birches-Roy Funeral Home
- Best Hotel/Motel – The Little Lion
- Best Landscaping/Lawn Care – Four One Tree & Landscape LLC
- Best Moving/Storage Company – Camel Moving
- Best Nursing Home/Retirement Community – Kimball Farms Life Care
- Best Pediatrician – MACONY Pediatric and Adolescent Medicine
- Best Physician – Dr. Blake Williams, M.D.
- Best Place to Work – Lee Bank
- Best Real Estate Agent – Karen Climo at William Pitt Sotheby’s
- Best Salon/Barbershop – Seven Salon Spa
- Best Veterinarian – Bilmar Veterinary Services
- Best Wealth Management – October Mountain Financial Advisors
Shopping
- Best Antiques Dealer – West By East
- Best Auto Dealer – Haddad Auto Group
- Best Bike Shop – Berkshire Bike & Board
- Best Book Store – The Bookstore in Lenox
- Best Cannabis Dispensary – Calyx Berkshire Dispensary
- Best Furniture Store – Paul Rich & Sons
- Best Gallery – An American Craftsman Galleries
- Best Garden Center – Ward’s Nursery & Garden Center
- Best Gift Shop – Crystal Essence
- 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 – Big Y
- Best Resale Shop – Catwalk Boutique
- Best Toy Store – Tom’s Toys
- Best Women’s Clothing – Main Street