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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

November 2026

Yuri Gorbachev 23rd Annual Exhibition at The Byrne Gallery

The Byrne Gallery announces its 31st anniversary this year with a celebration and exhibition of vivid oil and enamel paintings of internationally acclaimed artist Yuri Gorbachev. The Byrne Gallery welcomes Yuri Gorbachev for his 23rd annual exhibition in Middleburg, Virginia. The Gallery will feature some of his classic paintings along with new works from his […]
Nov 04 - Jan 03
All Day
The Byrne Gallery
7 W Washington St, Middleburg, VA 20117
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Rue de Noel Emmanuel Christmas Shop

Rue de Noel Emmanuel Christmas Shop has all the charm, color, and holiday magic that make it one of Middleburg’s most anticipated traditions. Emmanuel Church transforms into a lively Christmas market filled with inspired gifts, festive decorations, gourmet treats, and one of a kind finds you will not see anywhere else. It is a joyful […]
Nov 12 - 15
10:00 am - 6:00 pm
Emmanuel Parish House
105 E Washington St, Middleburg, VA 20117
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Seasonal Wreath Workshop

Jenn Pineau will be in the backyard at Nature Composed leading a Seasonal Wreath Workshop! This in-person event offers a wonderful opportunity to create unique, handcrafted wreaths that celebrate the season. This workshop is perfect for all ages and skill levels and all materials are provided. Come experience the joy of wreathmaking in the garden! […]
Nov 14
9:30 am - 12:00 pm
Nature Composed
12 South Pendleton Street, Middleburg, VA 20117
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Cana’s Annual Crafts and Cheer

It’s the most wonderful time of the year: Crafts & Cheer! Enjoy a festive afternoon at the winery sipping on cozy hot mulled wine while shopping a local artisan market, or enjoy a decked out hot chocolate bar, espresso drinks, and treats at Black Oak Café. Special holiday release wine collection sets will be available […]
Nov 14
11:00 am - 6:00 pm
Cana Vineyards & Winery
38600 Little River Turnpike, Middleburg, VA 20117
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Easy as Pie Wine Tasting

  Indulge in four delicious holiday-inspired creations, each thoughtfully paired with a Boxwood wine. From savory quiche to decadent chocolate tartlets, discover how the right wine can elevate every bite. Pairing Menu Almond Frangipane Tartlet with Apricot Preserves Paired with Cupola 2025 — Sauvignon Blanc & Sauvignon Gris Butternut Squash Quiche Paired with Rosé 2025 […]
Nov 14
12:00 pm - 2:00 pm
Boxwood Estate Winery
2042 Burrland Ln, Middleburg, VA 20117
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Cheese Board Paint and Sip

Celebrate the holiday season with a cozy afternoon of painting at Cana Vineyards during our Annual Crafts and Cheer holiday market. Enjoy the breathtaking views at one of Virginia’s most beautiful wineries while creating a festive cheese board painting class. No experience is needed. Your ticket includes all painting supplies, step-by-step instruction, and your first […]
Nov 14
1:00 pm - 3:00 pm
Cana Vineyards & Winery
38600 Little River Turnpike, Middleburg, VA 20117
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Hunger Games Trivia

Celebrate the release of the new movie The Hunger Games: Sunrise on the Reaping with trivia, prizes, and fun! May the odds be ever in your favor. For ages 21+. Location: Chrysalis Vineyards, 39025 Little River Turnpike, Middleburg.
Nov 14
2:00 pm - 3:00 pm
Chrysalis Vineyards
39025 Little River Turnpike, Middleburg, VA 20117
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Loudoun Lyric Opera presents Mozart’s “Così fan tutte”

Dive into the wit and wonder of human comedy with Mozart’s Cosi fan tutte at St. David’s Episcopal Church in Ashburn, Va. One night only, prepare to be swept away by Mozart’s ingenious work, brought to life in a captivating semi-staged concert production. This exquisite presentation, accompanied by live orchestra, will delight families of all […]
Nov 14
7:00 pm - 9:00 pm
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Savenac 1821 Jewelry Trunk Show

Discover the distinctive designs of Savenac 1821 at a special two-day jewelry trunk show at the Residences at Salamander Sales Gallery. Browse a curated collection of beautiful pieces and explore jewelry that brings artistry and individuality to every occasion. The Residences at Salamander Gallery is located at 100 West Washington Street.
Nov 19
10:00 am - 6:00 pm
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Viva Community Holiday Toy and Gift Drive

Join Viva Community for a Holiday Toy and Gift Drive in partnership with Emmanuel Middleburg and stop by the Parish House with a toy or gift card, listen to holiday music, and partake in festive cookies and beverages! Viva Community is a bilingual outreach program that supports local families, especially those with limited resources, through […]
Nov 19
5:00 pm - 8:00 pm
Emmanuel Parish House
105 E Washington St, Middleburg, VA 20117
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