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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
February 2026

Adventures Through Grief

Discover a unique approach to coping with grief through Blue Ridge Care’s FREE tabletop role playing game-based Adventures Through Grief program. Grief counselors act as game masters, guiding participants on a meaningful quest to navigate life after the death of someone significant to them. No prior role-playing game experience necessary. An application is required. Loudoun […]
Feb 10
5:45 pm - 7:45 pm
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Valentine’s Day Experience

The Red Fox Culinary Team has crafted a spectacular Valentine’s Day dinner menu, featuring refined game and seafood selections including oysters, halibut and venison. Each dish is curated with the finest ingredients from Virginia’s Piedmont and bountiful south and is inspired by the warmth and tradition of the winter season. Click here to learn more […]
Feb 12 - 16
All Day
Red Fox Inn & Tavern
2 East Washington St, Middleburg, Va 20117
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Briar Patch Cooking Class Weekend

Briar Patch is offering winter cooking classes and a stay for folks who want to try something new in the kitchen while staying at the inn! What’s Included Two-night stay with hot breakfasts Saturday and Sunday Friday night wine tasting with a local winery expert and hors d’oeuvres Saturday evening cooking demonstration and four-course dinner […]
Feb 13 - 14
All Day
Briar Patch B&B
23130 Briar Patch Lane, Middleburg, VA 20117
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Valentine’s Game Night

Celebrate Valentine’s Day with a fun-filled Game Night at Lost Barrel Brewing! All games and supplies will be provided for free, just bring your favorite people. Groups of any size are welcome, with tables available on a first come, first served basis. Enjoy our large food and drink menu with something for everyone while games […]
Feb 13
4:00 pm - 9:30 pm
Lost Barrel Brewing
36138 John Mosby Hwy, Middleburg, VA 20117
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“This Ol’ Country Girl” Fifth Annual Patsy Cline Concert

Experience the unforgettable music of Patsy Cline at our 5th Annual Tribute Concert. This special performance by Bess Putnam brings Patsy’s iconic songs to life while sharing the story of her journeys in the Shenandoah and Piedmont regions. Discover how her local roots helped launch one of the most legendary voices in American music. Beer, […]
Feb 13
7:00 pm - 9:00 pm
Buchanan Hall
8549 John S. Mosby Hwy. Upperville, VA 20184
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