Food & Drink
- Best Bakery – Berkshire Mountain Bakery
- Best Bar – Barrington Brewery & Restaurant
- Best Breakfast – GB Eats
- Best Brewery/Distillery – Berkshire Mountain Distillers
- Best Burger – The Bistro Box
- Best Butcher – Mazzeo’s Meat and Seafood
- Best Coffee Shop – Six Depot Roastery & Cafe
- Best Fine Dining – The Old Inn on the Green
- Best Grocery Store – Guido’s Fresh Marketplace
- Best Ice Cream – High Lawn Farm
- Best International Cuisine – Jae’s at the Hilton Garden Inn
- Best Liquor Store – Spirited Wines
- Best Mexican Food – Xicohtencatl
- Best Organic Food – Berkshire Food Co-op
- Best Pizza – Roberto’s Pizza
- Best Restaurant – Cafe Adam
- Best Winery – Balderdash Cellars
Recreation
- Best Concert Venue – Tanglewood
- Best Fitness Gym – Berkshire South Regional Community Center
- Best Golf Course – Wyantenuck Country Club
- Best Museum – Norman Rockwell Museum
- Best Outdoor Recreation – Ski Butternut
Services
- Best Auto Repair – Ormsbee’s Garage
- Best Bank – Greylock Federal Credit Union
- Best Community Service Organization – Greenagers
- Best Contractor – Morrison’s Home Improvement
- Best Dentist – Krol & Nazarov, P.C.
- Best Event Planner – Only In My Dreams
- Best Florist – Wildflowers
- Best Funeral Home – Finnerty & Stevens Funeral Home
- Best Hotel/Motel – The Red Lion Inn
- Best Landscaping/Lawn Care – Hils Lawn & Property Care
- 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. Gabriel Naventi, M.D.
- Best Place to Work – Berkshire Money Management
- Best Real Estate Agent – Karen Climo at William Pitt Sotheby’s
- Best Salon/Barbershop – Michele’s Salon & Day Spa
- Best Veterinarian – Bilmar Veterinary Services
- Best Wealth Management – Berkshire Money Management
Shopping
- Best Antiques Dealer – Elise Abrams Antiques
- Best Auto Dealer – Haddad Auto Group
- Best Bike Shop – Berkshire Bike & Board
- Best Book Store – The Bookloft
- Best Cannabis Dispensary – Devine
- Best Furniture Store – Paul Rich & Sons
- Best Gallery – RA Gallery
- Best Garden Center – Ward’s Nursery & Garden Center
- Best Gift Shop – Crystal Essence
- Best Hardware Store – Carr Hardware
- Best Jeweler – Zabian’s Fine Jewelers
- Best Men’s Clothing – Zabian’s Clothing
- Best Pet Supplies/Services – Pawsh Buddies
- Best Pharmacy – Big Y
- Best Resale Shop – Catwalk Boutique
- Best Toy Store – Tom’s Toys
- Best Women’s Clothing – Barrington Outfitters