| The Robert C. Memorial Hospital, Inc. | Health Care and Social Assistance | $1,529,630 | $1,551,172 | 113 | $19.2M |  Research |
| Geer Woods, Inc. | Health Care and Social Assistance | $739,617 | $749,622 | 62 | N/A | Research |
| Stadium System Inc. | Other Services (except Public Administration) | $722,988 | $732,654 | 51 | $10.0M | Research |
| Stadium System, Inc. | Retail Trade | $715,650 | $722,924 | 74 | $17.4M | Research |
| Geer Woods INC | Health Care and Social Assistance | $627,510 | $635,807 | 45 | N/A | Research |
| Decker & Beebe, Incorporated | Construction | $369,366 | $372,311 | 21 | $6.6M | Research |
| Lindell Fuels, Inc. | Retail Trade | $286,386 | $288,223 | 21 | $5.0M | Research |
| The Geer Corporaton | Health Care and Social Assistance | $258,065 | $261,556 | 16 | N/A | Research |
| Hutzler Manufacturing Co., Inc. | Manufacturing | $212,602 | $213,965 | 19 | <$5M | Research |
| Arnold's Garage LLC | Other Services (except Public Administration) | $168,753 | $170,783 | 15 | <$5M | Research |
| Arnold's Garage, LLC | Other Services (except Public Administration) | $147,497 | $149,130 | 23 | <$5M | Research |
| Pallone/karcheski, LLC | Construction | $137,420 | $138,208 | 14 | <$5M | Research |
| Allyndale Corporation | Mining, Quarrying, and Oil and Gas Extraction | $129,460 | $130,531 | 13 | <$5M | Research |
| Cornwall Plumbing & Heating LLC | Construction | $124,525 | $125,624 | 10 | <$5M | Research |
| Vollmer America INC | Wholesale Trade | $118,665 | $119,309 | 8 | <$5M | Research |
| Housatonic Valley Dental Care PC | Health Care and Social Assistance | $118,107 | $119,379 | 8 | <$5M | Research |
| Vollmer America, Inc. | Wholesale Trade | $116,394 | $117,392 | 7 | <$5M | Research |
| Housatonic Valley Dental Care | Health Care and Social Assistance | $115,654 | $103,679 | 6 | <$5M | Research |
| State Line Pizza INC | Accommodation and Food Services | $110,134 | $111,356 | 16 | <$5M | Research |
| Cornwall Plumbing & Heating, LLC | Construction | $106,621 | $107,524 | 11 | <$5M | Research |
| Greenacres Landscaping of Canaan Ct LLC | Administrative and Support and Waste Management | $104,792 | $105,757 | 8 | <$5M | Research |
| Dave's Tire and Auto Repair | Other Services (except Public Administration) | $101,478 | $102,137 | 10 | <$5M | Research |
| Segalla's Turnkey Housing, LLC | Retail Trade | $100,127 | $101,013 | 9 | <$5M | Research |
| C.a. Lindell & Son, Inc. | Retail Trade | $100,000 | $100,567 | 17 | <$5M | Research |
| Art Farm Property Management INC | Real Estate and Rental and Leasing | $91,462 | $92,216 | 6 | <$5M | Research |