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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
Monthly Weekly Daily List
May 2026

Places in My Heart

This May, The Byrne Gallery will showcase five artists—Craig Arnold, Laura Bollettino, Katie Flack, Tobin Karicher, and Anne Stine—as they present their most cherished interpretations of the landscapes that inspire them. Their paintings invite viewers on a journey through the season of renewal. Additionally, an artists’ reception will be held on May 16 from 4–7 pm, […]
May 06 - 31
8:00 am - 6:00 pm
The Byrne Gallery
7 W Washington St, Middleburg, VA 20117
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Designer Jewelry Show

To celebrate 35 years of fine jewelry excellence, Mystique Jewelers is proud to host a one-day-only trunk show featuring the world-renowned Mazza Company. The Mazza family’s legacy in the jewelry industry dates back nearly two centuries to Torre del Greco, Italy. Beginning in the 1840s, the family gained fame for harvesting and hand-carving exquisite coral […]
May 07 - 08
10:30 am - 5:30 pm
Mystique Jewelers
112 West Washington Street, Middleburg, Virginia 20117
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iPhone Photography with Photographer Jeff Mauritzen

Bring your smartphone to this fun, hands-on demonstration and learn how to become a better photographer and storyteller with both technical and creative tips. For over 13 years, Mauritzen has been guiding and lecturing as a photography expert for National Geographic Expeditions. Learn more about his work here or click here to follow him on […]
May 07
7:00 pm - 8:00 pm
Middleburg Library
101 Reed St, Middleburg, VA 20117
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Hill School Spring Weekend & Centennial Gala

The Hill School, celebrating a century of education, character, and connection, invites the community to return for a Spring Weekend honoring the memories formed, lessons learned, and bonds that endure. This Centennial gathering pays tribute to the past, embraces the joy of the present, and looks ahead with gratitude and anticipation to the next 100 […]
May 08 - 09
8:00 am - 6:00 pm
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Free Concert Series: Green Leaf Society

Enjoy a spring evening of live music at the Middleburg Community Center featuring Green Leaf Society as part of the Free Concert Series. Held in MCC’s outdoor amphitheater, guests are encouraged to bring a lawn chair or picnic blanket and settle in for a relaxed evening under the open sky. Pack a picnic, gather with […]
May 08
6:30 pm - 8:30 pm
Middleburg Community Center
300 W Washington St, Middleburg, VA 20117
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Live Music Series with Dennis Wayland

Join Cana Vineyards for their live music series! Dennis Wayland is a singer/songwriter from Manassas, Virginia who has a five song EP that was recorded in Nashville called Between Love and Rock N’ Roll as well as two solo albums to his credit. The music he writes is heavily influenced by classic country ballads, southern […]
May 09
12:00 pm - 4:00 pm
Cana Vineyards & Winery
38600 Little River Turnpike, Middleburg, VA 20117
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