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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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“The Animal in Art: Highlight the Horse, Fox and Hound” Exhibit

The Artists in Middleburg annual Animals in Art: Highlighting the Horse, Fox and Hound exhibition celebrates the beauty, spirit, and tradition of the horse, fox, and hound. This show honors the animals that are central to our region’s landscape and heritage. It represents 50 local artists with all new work.
May 09 - Jun 14
All Day
The Artists in Middleburg
102 W Washington St, Middleburg, VA 20117
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May Sale

Once monthly sale of Fine Furnishings and Fabulous Finds– upholstered furniture, tables, chairs, art, rugs, mirrors, lamps, decor and collectibles. Antique, vintage and new. Barn basement full of high-end items to create a beautiful, collected home.
May 15
11:00 am - 5:00 pm
Another Blue Moon
119 The Plains Rd., Middleburg, VA 20117
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Guided Safari at Glenstone Farm

Choose your experience and explore conservation on a historic estate in Aldie, VA. Exact address provided at registration. Separate registration is required for the Friday Meadow Meander and Cocktail Reception. Tours are about 1.5 hours and led by conservation biologists, offering rare access to land in transition. Options include: • Bring Your Horse • Guided […]
May 16
9:00 am - 12:00 pm
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Slow Flow Yoga with Rhonda

Calm your mind and feel good in your body with Slow Flow Yoga at Cana Vineyards and Winery with Rhonda Wilson. This thoughtfully paced class weaves together breath and movement to help you feel grounded, centered, and at ease. You’ll learn simple techniques to quiet the mind, deepen your breath, and move through gentle sequences […]
May 16
9:30 am - 10:30 am
Cana Vineyards & Winery
38600 Little River Turnpike, Middleburg, VA 20117
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May Sale

Once monthly sale of Fine Furnishings and Fabulous Finds– upholstered furniture, tables, chairs, art, rugs, mirrors, lamps, decor and collectibles. Antique, vintage and new. Barn basement full of high-end items to create a beautiful, collected home.
May 16
11:00 am - 5:00 pm
Another Blue Moon
119 The Plains Rd., Middleburg, VA 20117
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Board Game Night

Join the Middleburg Library an evening of fun, strategy, and friendly competition at Chrysalis Vineyards. For ages 21+. The library is partnering with Chrysalis Vineyards to host a relaxed evening of games. Sip your favorite beverages while playing classic and modern board and card games. Whether you’re a seasoned strategist or just looking for a […]
May 16
4:00 pm - 7:30 pm
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Boots Bridles & Bling Barn Dance

Join Loudoun Therapeutic Riding for an unforgettable evening at the LTR Barn as we celebrate our most important fundraiser of the year! In the Year of the Horse, we’re welcoming our entire community to come together for a night of purpose, partnership, and plenty of fun. Enjoy a delicious dinner by Mission BBQ, along with […]
May 16
5:30 pm - 10:00 pm
Loudoun Therapeutic Riding
14490 Berlin Turnpike, Lovettsville, VA 20180
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