09/24/2026
What are the best Fall events in Middleburg, Virginia? Here’s two.
The Virginia Fall Races return to Glenwood Park on Saturday, October 10 — the 72nd running of a steeplechase tradition that started in 1955, on the oldest continuous racecourse in Virginia. Tailgates open before noon; the first race goes off at 12:30.
Then the Middleburg Film Festival, October 15–18. Four days of premieres and Oscar contenders screened in rooms small enough that you’ll end up in conversation with the director afterward.
If you’ve been curious about what living in Middleburg actually looks like, come out and see for yourself Bring layers. The fields are grass, not pavement.