| Cook County Hospital District | Health Care and Social Assistance | $1,436,250 | $1,443,950 | 148 | N/A |  Research |
| Sawtooth Mountain Clinic | Health Care and Social Assistance | $673,888 | $678,867 | 49 | N/A | Research |
| Hedstrom Lumber Company, Inc. | Manufacturing | $378,500 | $383,446 | 36 | $35.7M | Research |
| Northwind Sailing, INC | Accommodation and Food Services | $310,845 | $312,002 | 45 | $8.0M | Research |
| L. Jireh INC | Accommodation and Food Services | $238,000 | $240,056 | 40 | $12.5M | Research |
| Northwind Sailing, INC | Accommodation and Food Services | $222,033 | $223,401 | 35 | $6.2M | Research |
| Mj Resort, Inc. | Accommodation and Food Services | $202,900 | $204,329 | 27 | $8.4M | Research |
| Cook County Whole Foods Co-Op | Retail Trade | $201,105 | $202,189 | 41 | $10.2M | Research |
| Gene's Foods, INC | Retail Trade | $197,592 | $198,778 | 20 | <$5M | Research |
| Mike's Holiday, INC | Retail Trade | $192,523 | $193,742 | 22 | $7.4M | Research |
| Edwin E. Thoreson, Inc. | Mining, Quarrying, and Oil and Gas Extraction | $171,962 | $174,159 | 7 | <$5M | Research |
| North House Folk School | Educational Services | $158,350 | $159,555 | 20 | N/A | Research |
| North House Folk School | Educational Services | $155,793 | $156,554 | 14 | N/A | Research |
| Gun Flint Tavern On the Lake LLC | Accommodation and Food Services | $142,800 | $143,449 | 77 | $13.7M | Research |
| L Jireh, INC | Accommodation and Food Services | $140,345 | $141,199 | 26 | <$5M | Research |
| Mike's Holiday, INC | Retail Trade | $137,349 | $138,520 | 11 | <$5M | Research |
| Three Families Brewing LLC | Accommodation and Food Services | $135,482 | $136,254 | 20 | <$5M | Research |
| Grand Marais Family Dentistry PA | Health Care and Social Assistance | $126,740 | $127,386 | 12 | <$5M | Research |
| Grand Marais Family Dentistry, P.a. | Health Care and Social Assistance | $126,700 | $127,759 | 12 | <$5M | Research |
| Lake Superior Trading Post INC | Retail Trade | $126,684 | $127,071 | 20 | <$5M | Research |
| Adeptyx Consulting INC | Professional, Scientific, and Technical Services | $117,415 | $117,868 | 6 | <$5M | Research |
| Three Families Brewing LLC | Manufacturing | $117,100 | $117,763 | 20 | $7.1M | Research |
| Upstate Mn LLC | Retail Trade | $110,097 | $110,635 | 1 | <$5M | Research |
| Lake Superior Trading Post INC | Retail Trade | $101,347 | $102,234 | 20 | <$5M | Research |
| Grand Marais Investors, LLC | Retail Trade | $100,200 | $100,881 | 10 | <$5M | Research |