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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
July 2026

“Ocean Song” Exhibit

The Byrne Gallery in Middleburg, Virginia is pleased to announce our show for the months of July and August, Ocean Song. The show’s artwork will include oil paintings by local artists Gerald Hennesy, Shawn Hennesy, Jeff Kibler, and Victor Nizovstev. Their paintings transport the viewer to serene ocean views from up and down the East […]
Jul 01 - Aug 30
All Day
The Byrne Gallery
7 W Washington St, Middleburg, VA 20117
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August 2026

For the Common Defense

Local historian Jeff Joyce discusses how the Continental Army, Navy, and Marines were established in 1775, soon after the Revolutionary War broke out between the colonies and Great Britain. Jeff Joyce is an Air Force veteran and a retired defense contractor. He is a volunteer historian at Culpeper National Cemetery, supporting the Wreaths Across America […]
Aug 20
7:00 pm - 8:00 pm
Middleburg Library
101 Reed St, Middleburg, VA 20117
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The Greek Table — Five Courses, Five Greek Wines

For one unforgettable evening, Grayson’s at Goodstone Inn carries the spirit of the Greek table to the rolling pastures of Middleburg. This five-course dinner reimagines Mediterranean tradition through the estate’s farm-to-fork philosophy. Each plate is composed of produce grown on our own grounds and gathered from neighboring Hunt Country farms — and paired with a […]
Aug 25
6:00 pm - 9:00 pm
Goodstone Inn & Restaurant
36205 Snake Hill Rd, Middleburg, VA 20117
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College Football Tailgate

Calling all college football fans! KICK OFF the season at Loudoun Market and get GAMEDAY ready with lots of new arrivals inspired by Saturdays in the fall. Wear your favorite team’s logo and receive 10% off your entire purchase!
Aug 29
10:00 am - 6:00 pm
Loudoun Market
207 West Washington Street, Middleburg, VA 20117
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Sunday Sketch

Held the last Sunday of every month. Participation in the program is free and open to the public: no sign-up is required, and all necessary materials are provided. Visitors may also enjoy free admission to the Museum on these days, regardless of participation in the program. The NSLM reserves the right to cancel or reschedule […]
Aug 30
2:00 pm - 4:00 pm
National Sporting Library & Museum
102 The Plains Rd, Middleburg, VA 20117
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September 2026

“Horizons: Where Earth Meets Sky” Exhibit

The Byrne Gallery proudly presents Horizons: Where Earth Meets Sky, the new exhibition for the month of September. Local artists Laura Bollettino, Katie Flack, and Gerald Hennesy will explore the timeless beauty of the landscape and the quiet wonder found where land and sky converge. Through scenes of coastlines, fields, marshes, and mountains, the exhibition […]
Sep 02 - 27
All Day
The Byrne Gallery
7 W Washington St, Middleburg, VA 20117
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