| 1 | chemtura corporation, now part of the lanxess group | $490.7M | 3,000 | 70 |
| 2 | Culver Duck Farms, Inc. | $142.3M | 350 | 70 |
| 3 | Winnebago Towables | $69.4M | 350 | 60 |
| 4 | Earth's Best, Inc. | $63.5M | 125 | 60 |
| 5 | Counseling Service of Addison County, Inc | $58.4M | 350 | 60 |
| 6 | Agway Energy Products | $34.3M | 125 | 60 |
| 7 | Otter Creek Brewing Company | $30.8M | 125 | 60 |
| 8 | Entech, Inc | $28.2M | 125 | 60 |
| 9 | BillMo | $26.3M | 125 | 60 |
| 10 | Middlebury Women on Wall Street | $26.3M | 125 | 60 |
| 11 | PIC Design - Precision Gears and Mechanical Components | $25.0M | 125 | 60 |
| 12 | The University of Vermont Health Network- Porter Medical Center | $24.4M | 146 | 60 |
| 13 | Royal RV & Auto Center | $23.8M | 125 | 60 |
| 14 | ZIGGITY SYSTEMS, INC | $17.8M | 30 | 60 |
| 15 | Rise’n Roll | $15.3M | 30 | 60 |
| 16 | middlebury language tables | $14.3M | 125 | 60 |
| 17 | Middlebury College SGA: Student Government Association | $12.6M | 125 | 60 |
| 18 | Holden Insurance, a division of The Richards Group | $11.0M | 30 | 60 |
| 19 | Holden Financial Services Inc | $11.0M | 30 | 60 |
| 20 | GrilleMe LLC | $8.2M | 30 | 50 |
| 21 | Vermont Coffee Company | $7.4M | 30 | 50 |
| 22 | Middlebury Foods | $7.4M | 30 | 50 |
| 23 | Biggabed | $7.2M | 30 | 50 |
| 24 | K & N Furniture | $7.2M | 30 | 50 |
| 25 | addison central school district (vermont) | $6.9M | 350 | 50 |
| 26 | Pulse 4 Pulse | $6.7M | 125 | 50 |
| 27 | J&L Medical Services | $6.7M | 125 | 50 |
| 28 | Seedsheet | $6.6M | 30 | 50 |
| 29 | Vermont Country Soap Corp | $6.6M | 30 | 50 |
| 30 | Satori VT | $6.6M | 30 | 50 |
| 31 | iSend, LLC | $6.3M | 30 | 50 |
| 32 | Waterbury CT Teachers Federal Credit Union - WCTFCU | $6.3M | 30 | 50 |
| 33 | foster motors inc | $5.7M | 30 | 50 |
| 34 | j & l's cargo express, inc. | $5.7M | 30 | 50 |
| 35 | Vemas | $5.7M | 30 | 50 |
| 36 | Paul Dinto Electrical Contrs | $5.7M | 30 | 50 |
| 37 | Softstart Services Inc | $5.1M | 30 | 50 |
| 38 | middlebury transitional care coalition inc | $5.0M | 30 | 50 |
| 39 | middlebury pediatric and adolescent medicine | $5.0M | 30 | 50 |
| 40 | Connecticut Counseling Ctr Inc | $5.0M | 30 | 50 |
| 41 | active orthopaedics, p.c | $5.0M | 30 | 50 |
| 42 | McDaniel Chiropractic Center | $5.0M | 30 | 50 |
| 43 | Doral Steel Co | $4.9M | 30 | 50 |
| 44 | Patchwork Quilt Country Inn | $4.9M | 30 | 50 |
| 45 | Illusso | $4.9M | 30 | 50 |
| 46 | COURT HOUSE SQUARE LLC | $4.9M | 30 | 50 |
| 47 | lock-n-glass crafters, llc | $4.5M | 30 | 50 |
| 48 | Victorian Homes Inc | $4.5M | 30 | 50 |
| 49 | Oratory Now | $4.1M | 125 | 50 |
| 50 | ziggity systems inc | $4.1M | 30 | 50 |
| 51 | Unidel LLC | $3.8M | 125 | 50 |
| 52 | Vermont Magazine | $3.8M | 30 | 50 |
| 53 | cae associates, inc | $3.7M | 30 | 50 |
| 54 | Middlebury Old Stone Mill | $3.4M | 30 | 50 |
| 55 | Middlebury Model United Nations | $3.4M | 30 | 50 |
| 56 | Middlebury College Center for Careers and Internships | $3.4M | 30 | 50 |
| 57 | Service Translation | $3.4M | 30 | 50 |
| 58 | Middlebury College International Students' Organization | $3.4M | 30 | 50 |
| 59 | Crompton Corporation | $3.3M | 5 | 50 |
| 60 | Middlebury Consulting Group | $3.1M | 125 | 50 |
| 61 | Clover Magazine | $3.0M | 30 | 50 |
| 62 | Beau Ties of Vermont | $3.0M | 30 | 50 |
| 63 | Northern Steel Alliance LLC. | $3.0M | 5 | 50 |
| 64 | MSM Global One, LLC | $3.0M | 5 | 50 |
| 65 | Atlas I.T. | $2.8M | 30 | 50 |
| 66 | Quicktech Consulting LLC | $2.8M | 30 | 50 |
| 67 | studio 7 boutique | $2.8M | 30 | 50 |
| 68 | Jaci Carroll Staffing, Inc. | $2.6M | 30 | 50 |
| 69 | American Retroworks - Good Point Recycling | $2.2M | 30 | 50 |
| 70 | sunday night environmental group (sneg) | $2.2M | 30 | 50 |
| 71 | Middlebury Discount Beverage | $2.1M | 5 | 50 |
| 72 | EPCO SALES, INC. | $2.1M | 5 | 50 |
| 73 | glo skin care & anti-aging boutique | $2.1M | 5 | 50 |
| 74 | another best day | $2.0M | 5 | 50 |
| 75 | Marble Works Partnership | $2.0M | 5 | 50 |
| 76 | The Middlebury Shop (Forth 'N Goal Sports) | $2.0M | 5 | 50 |
| 77 | 5 star investment group, llc | $2.0M | 30 | 50 |
| 78 | weichert realtors heritage pro | $2.0M | 30 | 50 |
| 79 | Phinney Properties Inc | $2.0M | 30 | 50 |
| 80 | realty executives icon llc. | $2.0M | 30 | 50 |
| 81 | LABERGE INSURANCE AGENCY, INC. | $1.8M | 5 | 50 |
| 82 | tamid group at middlebury college | $1.8M | 30 | 50 |
| 83 | fiduciam financial, a private wealth advisory practice of ameriprise financial services, llc | $1.8M | 30 | 50 |
| 84 | Otter Creek Child Center Inc | $1.6M | 30 | 50 |
| 85 | MIDDLEBURY CONVALESCENT HOME, INC | $1.6M | 30 | 50 |
| 86 | Porter Health Systems, Inc | $1.6M | 30 | 50 |
| 87 | Firefly Home Care | $1.6M | 30 | 50 |
| 88 | vb holdings | $1.6M | 30 | 50 |
| 89 | DEPPMAN & FOLEY P.C. | $1.5M | 30 | 50 |
| 90 | Middlebury Schools Abroad | $1.5M | 125 | 50 |
| 91 | Green Peppers Restaurant | $1.2M | 5 | 50 |
| 92 | Northeast Drinks Group | $1.2M | 5 | 50 |
| 93 | Iluminar Coffee & Bud's Beans | $1.2M | 5 | 50 |
| 94 | doria’s restaurant | $1.2M | 30 | 50 |
| 95 | pies & pints of middlebury | $1.2M | 30 | 50 |
| 96 | chubba’s bagelry | $1.2M | 30 | 50 |
| 97 | that pretty place | $1.2M | 30 | 50 |
| 98 | essenhaus country inn | $1.2M | 30 | 50 |
| 99 | on the creek bed and breakfast. | $1.2M | 30 | 50 |
| 100 | courtyard middlebury | $1.2M | 30 | 50 |