- Racing Car Supplies, Bennington
- Radio Stations & Broadcasting Companies, Bennington
- Ready Mix Concrete, Bennington - Concrete Suppliers, Dealers & Company
- Ready Mix Concrete Producers, Bennington
- Real Estate, Bennington - Agent, Broker & Companies
- Real Estate Agent - Property Lessors, Bennington
- Real Estate Appraisers & Consulting Services, Bennington
- Real Estate Consultants, Bennington
- Real Estate Rentals, Bennington
- Real Estate Services, Bennington
- Recycling Drop-Off Centers, Bennington
- Refrigeration & Cooling Equipment, Parts & Supplies , Bennington - Water Cooler, Ice Machine, Beverage Dispenser, etc
- Refrigeration Repair & Service, Bennington - Ac, Freezer, Refrigerator Repair
- Rehabilitation Centers, Products & Services, Bennington
- Rehabilitation Specialists, Bennington
- Relief Organizations, Bennington
- Religious Education, Bennington
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- Religious Organizations, Bennington
- Rental & Leasing Business Equipment, Bennington
- Repair Services, Bennington
- Research Services, Bennington
- Residential, Bennington
- Residential Apartments, Bennington
- Residential Care Facilities, Bennington
- Residential Construction Contractors, Bennington - General Contractors
- Restaurants/Food & Dining, Bennington
- Retail Book Stores, Bennington
- Retirement Communities & Home, Assisted Living & Apartments, Bennington
- Riding Equipment, Bennington
- Rodeo & Equestrian Equipment & Supplies, Bennington
- Roofing Consultants, Bennington - Roofing Companies
- Roofing Contractors, Bennington - Roof Repair, Cleaning, Installation & Maintenance - Roofers
- Roofing Materials & Supplies, Bennington
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