| Men |
| Men Overall (Williamsburg Jaycees Run for Life) |
| Michael Mann, 33 Hampton 33:04 (2002) |
| Men 14-and-under (Run for the Hills 10K) |
| John Carlson, 14 Signal Mountain, TN 39:30 (2012) |
| Men 15-19 (Run for the Hills 10K) |
| Brian McManus, 18 Williamsburg 41:18 (2014) |
| Men 20-24 (Run for the Hills 10K) |
| Skeeter Morris, 23 Burkeville 33:35 (2011) |
| Men 25-29 (Victory at Yorktown 10K) |
| Paul Balmer, 27 Washington, DC 33:14 (2017) |
| Men 30-34 (Williamsburg Jaycees Run for Life) |
| Michael Mann, 33 Hampton 33:04 (2002) |
| Men 35-39 (Jamestown 4-H Discovery Run) |
| Mark Tompkins, 39 Williamsburg 35:25 (2015) |
| Men 40-44 (Run for the Hills 10K) |
| Daniel Shaye, 41 Williamsburg 37:44 (2010) |
| Men 45-49 (Williamsburg Jaycees Run for Life) |
| Jim Bates, 46 Hampton 35:48 (2002) |
| Men 50-54 (Victory at Yorktown 10K) |
| John Piggott, 50 Williamsburg 36:31 (2016) |
| Men 55-59 (Run for the Hills 10K) |
| Steve Chantry, 57 Williamsburg 37:37 (2012) |
| Men 60-64 (Victory at Yorktown 10K) |
| Stephen Chantry, 62 Williamsburg 39:36 (2017) |
| Men 65-69 (Run for the Hills 10K) |
| Larry Coley, 68 Chesapeake 46:03 (2016) |
| Men 70-74 (Williamsburg Jaycees Run for Life) |
| Tom Ray, 70 Kitty Hawk, NC 44:42 (2003) |
| Men 75-79 (Democracy Dash 10K at Jamestowne Island) |
| Ben Dyer, 75 Toano 50:06 (2018) |
| Men 80-84 (Jamestown 4-H Discovery Run) |
| Ernest Schillinger, 84 Williamsburg 1:19:03 (2016) |
| Men 85-89 (Jamestown 4-H Discovery Run) |
| Ernest Schillinger, 85 Williamsburg 1:24:19 (2017) |
| Men 90-and-over (Victory at Yorktown 10K) |
| Robert S. White, 93 Hampton 1:48:01 (2017)* |
| *Virginia state record for men 90-94 |
| Men’s Walk (Williamsburg Jaycees Run for Life) |
| Ray Funkhouser, 52 White Stone 53:49 (2003) |