| Date | Organization / Event / Contact | Site | Town |
| May 2 | Stonewall Hounds Trail Ride | ||
| May 6 | Rockbridge Hunt Trail Ride Cindy Morton, mortonc@wlu.edu 540-463-6025, 540-458-8109 | Windward Farm | Natural Bridge |
| May 6 | Rockbridge Hunt Trail Ride Cindy Morton, mortonc@wlu.edu 540-463-6025, 540-458-8109 | Windward Farm | Natural Bridge |
| May 6 | Glenmore Hunt Hound Show & Derby Day Party | Churchville | |
| May 6 | Oak Ridge Fox Hunt Club Trail Ride | Tea Time Farm | Afton |
| May 6 | Princess Anne Hunt Trail Ride Pam Martin, pam.martin@cox.net Cherylle Wornom, 757-253-0325 | Dogham Farm | Charles City |
| May 6 | Roanoke Valley Horse Rescue Derby Day Fundraiser and Barn Dance | Edge Hill Farm | Shawsville |
| May 6 | Virginia Gold Cup Race Meet | Great Meadow | The Plains |
| May 7 | Blue Ridge Hunt Trail Ride Emily Day, 540-837-1422 | Pigeon Hil | Berryville |
| May 7 | Bull Run Hunt Point-to-Point | Brandywine Park | Culpeper |
| May 9 | Stonewall Hounds Trail Ride | The Meadows | |
| May 10 | Rockbridge Hunt Annual Meeting | Tex Tilson Lodge at Hunt, Inc. | Natural Bridge |
| May 13 | Rockbridge Hunt Spring Hunter Pace Fred Burks, montafon@cfw.com 540-258-2828 | Windward Farm | Natural Bridge |
| May 13 | Bedford County Hunt Hunter Pace and Point-to-Point Races Dick Long, 540-297-3419 | Wolf Branch Farm | Forest |
| May 13 | Old Dominion Hounds Trail Ride | Hawthorne Farm | Orlean |
| May 14 | Blue Ridge Hunt Trail Ride Emily Day, 540-837-1422 | Fox Spring Woods Farm | Millwood |
| May 14 | Hoofbeats Therapeutic Riding Center Benefit Trail Ride Fundraiser HTRC, 540-464-3337 | Broadview Ranch | Lexington |
| May 16 | Stonewall Hounds Trail Ride | The Meadows | |
| May 20 | Old Dominion Hounds Trail Ride | High Meadow Farm | Flint Hill |
| May 21 | Blue Ridge Hunt Trail Ride Emily Day, 540-837-1422 | The Oaks | Millwood |
| May 21 | Farmington Hunt Club Walk-and-Talks Hunt line, 434-978-1107 Kay Butterfield, 434-823-5698 | Foxfield | Charlottesville |
| May 21 | Middlebrook Hounds Hunter Pace | Bold Stream Farm | Middlebrook |
| May 23 | Farmington Hunt Club Walk-and-Talks Hunt line, 434-978-1107 Kay Butterfield, 434-823-5698 | Schelford | Charlottesville |
| May 23 | Stonewall Hounds Trail Ride | ||
| May 27 | North American Point-to-Point Championship | Morven Park | Leesburg |
| May 27 | Oak Ridge Fox Hunt Club Trail Ride Becky Birnbaum, rab5s@virginia.edu | Tea Time Farm | Afton |
| May 28 | Rockbridge Hunt Clinic on Gymnastic Exercises Judy Mundy, jmundy@bcps.va.k12.us 540-473–3108 | Hunt, Inc. | Natural Bridge |
| May 28 | Blue Ridge Hunt Trail Ride Emily Day, 540-837-1422 | Oxbow Farm | Front Royal |
| May 28 | FCNA/MFHA Virginia Hound Show James Young, MFH, ranta@erols.com 540-364-1831 | Morven Park | Leesburg |
| May 29 | Farmington Hunt Club Walk-and-Talks Hunt line, 434-978-1107 Kay Butterfield, 434-823-5698 | The Barracks | Charlottesville |
You can generate a custom calendar for any listed organizations
| 2006 | January | February | March | April | May | June | July | August | September | October | November | December | |
| For Virginia: | Educational Programs | Horse Shows | Hound Competitions | Hunter Paces and Trials | Paneling | Races | Social Events | Special Hunt Meets | Trail Rides | |