Loudoun County, Virginia, is known as Virginia’s wine country and October is Virginia Wine Month, so there’s no better time to visit the region than now. Here are a few wine-related (and other) events to add to your trip itinerary.
The month kicked off with the 46th annual Virginia Wine Festival Oct. 1–2, but there’s wine fun to be had the entire month. Check out the full calendar of Virginia Wine Month events, taking place at different wineries throughout the region, ranging from special wine-pairing dinners to fall markets to live music events.

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Waterford Fair is a long-standing festival celebrating all things artisan in the mid-Atlantic. The fair, which takes place within a National Historic Landmark-designated historic village, features demonstrations, living historians, a juried art show, historic tours and more. The ticketed fair takes place Oct. 7–9.
When you think of famous film festivals, you might not automatically think of Middleburg Film Festival, but then you might be surprised at the famous faces that show up here. From Dakota Johnson to Viggo Mortensen to Emma Stone, the festival attracts a wide variety of actors, producers, filmmakers and other professionals for four days of film, Oct. 13–16.
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