| JANUARY | FEBRUARY | MARCH |
Fly Fishing Show |
Piedmont Fox Hounds Point-to-Point Orange County Hunt Point-to-Point |
|
| APRIL | MAY | JUNE |
Arbor Day Middleburg Spring Races Middleburg Hunt Point-to-Point |
Virginia Gold Cup Virginia Hunt Country Stable Tour Virginia Fox Hound Show |
Upperville Colt & Horse Show |
| JULY | AUGUST | SEPTEMBER |
Fourth of July Celebration Bluemont Concert Series |
Saturday Night Polo Annual Side Walk Sale Tomato Festival |
Middleburg Horse Trials Mosby Heritage History Weekend Celebrate the Harvest |
| OCTOBER | NOVEMBER | DECEMBER |
Virginia Fall Races Celebrate the Harvest Field Hunter Championship of America |
Christmas Shop |
Christmas in Middleburg |