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Local Events in Middleburg

Come & Join the Fun!

Renowned as the Nation’s Horse & Hunt Capital, Middleburg offers a variety of equestrian events throughout the year, including the Middleburg Spring Races and the Virginia Fall Races. It’s also a well-known destination for the arts with events like the Middleburg Film Festival and Art in the Burg.

Christmas in Middleburg draws thousands of visitors, who line the streets on the first Saturday in December to watch the parade and the Middleburg Hunt Revue.

Check the calendar below to find out what’s happening around town.

Audience in lawn chairs clapping in front of National Sporting Library and Museum
September 2026
October 2026

“Harvest: Celebrating Gatherings and Memories” Exhibit

The Byrne Gallery in Middleburg proudly presents Harvest: Celebrating Gatherings and Memories, a new exhibition in the month of October. This month, artist Sandra Iafrate will depict the beauty of the harvest season and the enduring connections between food, memory, family, and place. Iafrate’s use of collected materials and paint instills memories of gathering from […]
Oct 02 - Nov 01
All Day
The Byrne Gallery
7 W Washington St, Middleburg, VA 20117
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Coffee with a Cop

Coffee, conversation & community! Start the morning with Coffee with a Cop at Middleburg Common Grounds. Grab your favorite morning beverage and spend some time with the Middleburg Police Department and Loudoun County Sheriff’s Office. It’s a great chance to connect, ask questions, and get to know the officers who help keep our community safe. […]
Oct 07
8:30 am - 10:00 am
Middleburg Common Grounds
114 West Washington Street, Middleburg, VA 20117
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Movie Night: Alfred Hitchcock’s “Suspicion”

Join Middleburg Library for an Alfred Hitchcock movie every Wednesday night in October. Refreshments are provided. Watch Suspicion (TV-PG, 99 minutes). A shy, wealthy woman (Joan Fontaine) is courted by a charming troublemaker (Cary Grant), whom she marries and then begins to suspect will kill her.
Oct 07
6:00 pm - 8:00 pm
Middleburg Library
101 Reed St, Middleburg, VA 20117
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The Writer’s Eye: Writing Workshop with New York Times Bestselling Author Elizabeth Letts

The Writer’s Eye will be an intimate writing workshop led by #1 New York Times bestselling author and former NSLM John H. Daniels Fellowship recipient Elizabeth Letts. Drawing directly from her experience with the NSLM’s remarkable collections—including a selection of Library treasures and one striking large-scale work—Letts will guide participants through the art of finding […]
Oct 08
10:00 am - 1:00 pm
National Sporting Library & Museum
102 The Plains Rd, Middleburg, VA 20117
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From the Stacks to the Page: Elizabeth Letts on “Writing Fallen for France”

Join NSLM for an enchanting evening with #1 New York Times bestselling author and former NSLM John H. Daniels Fellowship recipient Elizabeth Letts as she shares the remarkable journey behind her latest novel, Fallen for France—a story born not from imagination alone, but from the very shelves of our Library’s collection. Letts will take us […]
Oct 08
5:00 pm - 7:00 pm
National Sporting Library & Museum
102 The Plains Rd, Middleburg, VA 20117
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Virginia Working Landscapes Nature Walk

Explore a beautiful farm near Atoka, Virginia, with Virginia Working Landscapes Biodiversity Technician Christopher Rademacher. As we walk through the farm’s grassland, wetland, and riverine ecosystems, we’ll look for migrating birds, discover native plants and wildlife, and take in the colorful beauty of the Virginia landscape in autumn. From falling leaves to late-blooming flowers, there’s […]
Oct 09
8:00 am - 10:00 am
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Foxtoberfest

Three Fox Vineyards & Brewery hosts its annual Foxtoberfest, featuring a full day of fox-themed fun. Guests can enjoy discounts for fox-themed attire and costumes, exclusive new wine and beer releases, wood-fired pizza and bratwurst, the Cornhole Classic Competition, live music, and a custom hat bar.
Oct 10
All Day
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Annual Harvest Festival

Save the date for Cana’s Annual Harvest Festival and toast to local agriculture, local artisanship, and our wonderful community during the fall harvest season. DRINKS: 11am-6pm, Last Call at 5:30pm Delicious Cana Vineyards wine, all proudly produced here in Middleburg. Don’t miss Cana’s signature fall mulled red wine! FOOD: 11am-5:30pm Black Oak Café: hot pizza, […]
Oct 10
11:00 am - 6:00 pm
Cana Vineyards & Winery
38600 Little River Turnpike, Middleburg, VA 20117
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