| Woodstock Resort Corporation | Accommodation and Food Services | $3,001,100 | $3,041,142 | 389 | $121.6M |  Research |
| Woodstock Resort Corporation | Accommodation and Food Services | $2,000,000 | $2,016,000 | 249 | $77.9M | Research |
| Chippers, Inc. | Administrative and Support and Waste Management | $822,400 | $828,258 | 70 | $15.2M | Research |
| Woodstock Farmers Market INC | Retail Trade | $486,051 | $488,808 | 100 | $11.1M | Research |
| Woodstock Farmers Market INC | Retail Trade | $468,800 | $471,986 | 100 | $11.1M | Research |
| Worthy Kitchen LLC | Accommodation and Food Services | $354,507 | $357,401 | 31 | $5.5M | Research |
| Manufacturing Information Systems INC | Information | $351,800 | $354,219 | 20 | <$5M | Research |
| Wild Apple Graphics, Ltd | Professional, Scientific, and Technical Services | $340,700 | $343,239 | 27 | $6.3M | Research |
| The Woodstock Foundation, Inc. | Arts, Entertainment, and Recreation | $332,400 | $337,491 | 34 | N/A | Research |
| Terrace Communities Woodstock, Llc. | Health Care and Social Assistance | $317,700 | $322,148 | 51 | $8.7M | Research |
| Woodstock Hospitality Inc. | Accommodation and Food Services | $282,352 | $284,038 | 82 | $25.6M | Research |
| Shillen Mackall & Seldon Law Office PC | Professional, Scientific, and Technical Services | $200,700 | $136,076 | 10 | <$5M | Research |
| P&p Restaurants LLC | Accommodation and Food Services | $192,713 | $194,841 | 42 | $7.5M | Research |
| Farmhouse Pottery, Inc. | Manufacturing | $183,100 | $185,498 | 23 | $22.8M | Research |
| C and M Washburn INC | Construction | $169,400 | $170,755 | 18 | $5.5M | Research |
| Andrew Pearce Bowls, LLC | Wholesale Trade | $163,400 | $164,353 | 19 | $5.8M | Research |
| Upland Construction LLC | Construction | $155,300 | $157,232 | 11 | <$5M | Research |
| Bradens LLC | Accommodation and Food Services | $145,386 | $146,545 | 21 | <$5M | Research |
| Fine Paints of Europe INC | Retail Trade | $143,000 | $144,406 | 11 | <$5M | Research |
| Jedidiah L Janissedmd and Associates Ltd | Health Care and Social Assistance | $140,736 | $141,842 | 11 | <$5M | Research |
| The Vermont Standard, Inc. | Professional, Scientific, and Technical Services | $129,900 | $130,661 | 12 | <$5M | Research |
| Bradens, LLC | Accommodation and Food Services | $128,600 | $105,764 | 25 | <$5M | Research |
| Mon Vert Cafe LLC | Accommodation and Food Services | $126,840 | $127,983 | 18 | <$5M | Research |
| Colby & Tobiason Custom Builders, INC | Construction | $125,800 | $126,834 | 11 | <$5M | Research |
| Woodstock Pharmacy INC | Retail Trade | $125,500 | $126,201 | 10 | <$5M | Research |