Food & Drink
- Best Bakery – Bakin’ Bakery
- Best Bar – The Well Restaurant + Bar
- Best Breakfast – GB Eats
- Best Burger – The Bistro Box
- Best Butcher – Mazzeo’s Meat and Seafood
- Best Coffee Shop – Fuel Bistro
- Best Distillery – Berkshire Mountain Distillers
- 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 & Fine Wines
- Best Mexican Food – Xicohtencatl
- Best Organic Food – Berkshire Food Co-op
- Best Pizza – Roberto’s Pizza
- Best Restaurant – The Marketplace Kitchen Table
- Best Winery – Le Trois Emme Winery
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 – John’s Garage & Auto Body
- Best Bank – Greylock Federal Credit Union
- Best Community Service Organization – Construct, Inc.
- Best Contractor – Morrison’s Home Improvement
- Best Dentist – Thomas Mullany
- Best Florist – Wildflowers Florist
- Best Funeral Home – Finnerty & Stevens Funeral Home
- Best Hotel/Motel – Red Lion Inn
- Best Landscaping/Lawn Care – Havens Lawn & Patio
- Best Nursing Home/Retirement Community – Geer Village Senior Community
- Best Pediatrician – MACONY Pediatric and Adolescent Medicine
- Best Physician – Daniel Patel, MD
- Best Place to Work – Taft Farms
- Best Real Estate Agent – Tiffany Roberts, Roberts & Associates Realty, Inc.
- Best Salon/Barbershop – Mulberry Hair Company
- Best Veterinarian – Bilmar Veterinary Services
- Best Wealth Management – Berkshire Money Management
Shopping
- Best Antiques Dealer – Mix on Main
- Best Auto Dealer – Bachetti’s Auto Sales
- Best Bike Shop – Berkshire Bike & Board
- Best Book Store – The Bookloft
- Best Cannabis Dispensary – Theory Wellness
- Best Consignment/Resale Shop – Catwalk Boutique
- Best Furniture Store – Hammertown
- Best Gallery – Saint Francis Gallery
- Best Garden Center – Ward’s Nursery & Garden Center
- Best Gift Shop – Hart Textiles
- Best Hardware Store – Carr Hardware
- Best Jeweler – Lennox Jewelers
- Best Men’s Clothing – Zabian’s Clothing
- Best Pet Supplies/Services – Agway
- Best Pharmacy – Big Y
- Best Toy Store – Tom’s Toys
- Best Women’s Clothing – MainStreet