| 135 Years | Ruby Concrete Co 134 Dempsey, Madisonville | 821-3870 |
| 127 Years | Knight & Sons [monuments] 302 W Center St, Madisonville | 821-7553 |
| 100 Years | Pleasant View Green House 418 Princeton Rd, Madisonville | 821-6144 |
| 95 Years | Clark Beshear & Clark 106 W Railroad Ave, Dawson Springs | 797-3211 |
| 95 Years | Beshear's Funeral Home 201 N Main St, Dawson Springs | 797-5165 |
| 89 Years | Riddle Insurance 245 S Main St, Madisonville | 821-3122 |
| 87 Years | The Messenger 221 S Main PO Box 529, Madisonville | 824-3300 |
| 83 Years | Barnett Strother Funeral Home 2285 N Main St, Madisonville | 821-7135 |
| 81 Years | Community First Bank South Main, Madisonville | 821-7211 |
| 79 Years | Prow Brothers Plumbing, Heating & Air Conditioning 1125 Island Ford Rd, Madisonville | 821-3400 |
| 77 Years | Ferrell's Snappy Service 112 N Main St, Madisonville | 821-7515 |
| 77 Years | Harris Funeral Home 134 N Main St, Madisonville | 821-6601 |
| 76 Years | Reid-Walters Funeral Home, Inc 302 Farren Ave, Earlington | 383-2821 |
| 72 Years | Modern Welding US Hwy 41A, Madisonville | 821-3575 |
| 69 Years | Joe Leasure & Sons Machine Shop 39 N Madison Ave, Madisonville | 821-3538 |
| 58 Years | Cates Oldsmobile - Cadillac, Inc. Madisonville | 821-4791 |
| 57 Years | Fugate Lumber 380 Park Ave, Madisonville | 821-3138 |
| 47 Years | Hart Equipment 1005 Nebo Rd, Madisonville | 821-4645 |
| 47 Years | Service Radiator, Inc 75 Dempsey, Madisonville | 821-4232 |
| 44 Years | Legate's Furniture 2112 S Main St,Madisonville | 821-2050 |
| 43 Years | Happy's [Office Supply] 62 S Main St Downtown, Madisonville | 821-6300 |
| 41 Years | Given's Book Exchange 155 W Center St, Madisonville | 821-1123 |
| 39 Years | Big "B" Cleaners 682 S Main, Madisonville | 825-1261 |
| 39 Years | R & D Electric Service 276 West Center, Madisonville | 821-7442 |
| 35 Years | W C Brown Construction Hwy 85 East, Madisonville | 821-1615 |
| 32 Years | Raymond's Wrecker Service 641 Pride Ave, Madisonville | 821-8186 |
| 29 Years | Hanner Machine 130 Pond River, Colliers Rd, Madisonville | 821-1947 |
| 25 Years | Sharkey's Westside Service Inc 820 W Noel, Madisonville | 821-3995 |
| 25 Years | Tucker's Cafe 571 E Center St [7 yrs], Madisonville [18 yrs formerly Alfords] | |
| 24 Years | Best Western Pennyrile Inn Exit 34 [Pennyrile Pkwy], Mortons Gap | 258-5201 |
| 23 Years | Carter Plumbing & Heating 325 W Arch St, Madisonville | 821-5254 |
| 17 Years | Hawkins Auto Body 77 Basset Ave, Madisonville | 821-2109 |
| 15 Years | E Z Shop # 5 1155 N Main St, Madisonville | 825-8752 |
| 14 Years | Quik-Change Oil'N'Lube Center 436 E Center, Madisonville | 821-0001 |
| 13 Years | On Target 1005 Pride Ave, Madisonville | 825-9098 |
| 13 Years | Uniform Boutique 50 Pritchett Ave, Madisonville | 825-4003 |
| 12 Years | Professional Eyecare Dr French 1350 S Main, Madisonville | 821-6241 |
| 12 Years | Father & Son's Liquors 36 Bassett Ave, Madisonville | 821-5078 |
| 11 Years | Bluegrass Home Medical 1200 N Main, Madisonville | 825-9661 |
| 8 Years | G.N.C 60 Madison Sq. Dr, Madisonville | 821-8183 |
| 5 Years | Backstreet Music 745 Grapevine Rd, Madisonville | 821-7274 |
| 5 Years | Dr Wittmer 240 East Ayr Parkway, Madisonville | 825-8345 |
| 5 Years | Carpet Barn 141 E Arch St, Madisonville | 821-2601 |
Rudd & Associates, Inc. Real Estate
458 N Main St, Madisonville 821-2426 www.ruddrealestate.com Debbie Enoch, GRI Chuck Lambdin Sally Salmon Sandy Newell, GRS Wanda Smith Cindy McKenzie Sonya Clardy, CRS Gale Lutz Sissy Lutz Tammy Clark Dee Martin, GRI Bill Rudd, GRI