| Washington Island Ferry Line, Inc. | Transportation and Warehousing | $341,000 | $343,283 | 27 | $6.8M | AI Deep Dive |
| Shipyard Island Marina INC | Real Estate and Rental and Leasing | $89,000 | $89,714 | 11 | <$5M | AI Deep Dive |
| Mann's Store Inc. | Retail Trade | $79,928 | $80,554 | 12 | <$5M | AI Deep Dive |
| Island Lavender LLC | Agriculture, Forestry, Fishing and Hunting | $68,000 | $68,463 | 13 | <$5M | AI Deep Dive |
| Hotel Washington & Studio LLC | Accommodation and Food Services | $51,906 | $52,155 | 21 | $6.6M | AI Deep Dive |
| Mann's Mercantile, Inc. | Retail Trade | $50,000 | $50,331 | 4 | <$5M | AI Deep Dive |
| Andermeyer LLC | Accommodation and Food Services | $48,457 | $48,835 | 3 | <$5M | AI Deep Dive |
| Koyen Collection LLC | Accommodation and Food Services | $47,297 | $47,564 | 11 | <$5M | AI Deep Dive |
| Island Builders LLC | Construction | $42,000 | $42,326 | 8 | <$5M | AI Deep Dive |
| Hotel Washington & Studio LLC | Accommodation and Food Services | $37,000 | $37,213 | 21 | $6.6M | AI Deep Dive |
| Lumoptik, Inc. | Manufacturing | $32,083 | $32,472 | 4 | <$5M | AI Deep Dive |
| Fragrant Isle LLC | Manufacturing | $32,000 | $58,429 | 15 | $14.9M | AI Deep Dive |
| Steffen's Cedar Lodge Inc. | Accommodation and Food Services | $28,000 | $28,262 | 4 | <$5M | AI Deep Dive |
| Dave Hanlin Garage LLC | Other Services (except Public Administration) | $27,022 | $27,147 | 6 | <$5M | AI Deep Dive |
| Trinity Evangelical Lutheran Church | Other Services (except Public Administration) | $27,000 | $27,187 | 7 | N/A | AI Deep Dive |
| Sailors Pub LLC | Accommodation and Food Services | $23,000 | $23,160 | 16 | <$5M | AI Deep Dive |
| Sawosko Enterprises Inc. | Accommodation and Food Services | $22,217 | $22,329 | 20 | <$5M | AI Deep Dive |
| Mcdonald Design/build LLC | Construction | $21,516 | $21,601 | 2 | <$5M | AI Deep Dive |
| Nelsen's Hall, Bitters Pub & Restaurant LLC | Accommodation and Food Services | $21,000 | $21,170 | 17 | <$5M | AI Deep Dive |
| Island Services LLC | Real Estate and Rental and Leasing | $20,833 | $20,941 | 1 | <$5M | AI Deep Dive |
| Frank Gibson | Health Care and Social Assistance | $20,833 | $0 | 1 | <$5M | AI Deep Dive |
| American Paper Machinery LLC | Professional, Scientific, and Technical Services | $20,833 | $20,948 | 1 | <$5M | AI Deep Dive |
| Hanlin Excavating & Trucking LLC | Construction | $20,832 | $20,949 | 1 | <$5M | AI Deep Dive |
| Trinity Evangelical Lutheran Church | Other Services (except Public Administration) | $20,040 | $20,110 | 7 | N/A | AI Deep Dive |
| American Paper Machinery, LLC | Wholesale Trade | $20,000 | $20,066 | 1 | <$5M | AI Deep Dive |