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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
January 2026

Annual Members Exhibit

Join the Artists in Middleburg in celebrating local creativity and art as we host the Annual Members Exhibit. This exhibit is juried and features 53 local artists exhibiting their best work of any subject. See paintings, photography, metal, bronze, ceramic and more. Proceeds from these exhibits help to support local art education.
Jan 08 - Feb 08
All Day
The Artists in Middleburg
102 W Washington St, Middleburg, VA 20117
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February 2026

Botanical Revolutions: A Book Talk with Giovanno Aloi

Join OSGF and Middleburg Books for a special Book Talk with Giovanni Aloi celebrating his new publication, Botanical Revolutions: How Plants Changed the Course of Art. The evening begins with a reception at 4:30 pm, followed by Dr. Aloi’s lecture at 5:00 pm and a brief Q&A. Copies of the book will be available for […]
Feb 04
4:30 pm - 6:30 pm
Oak Spring Garden Foundation
1776 Loughborough Lane, Upperville, VA 20184
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Reception, Discussion and Book Signing with Mark Shrager, author of “Diane Crump: A Horse-Racing Pioneer’s Life in the Saddle”

In 1968, a small group of women, dismissed by the press as “jockettes,” began demanding the right to apply for jockey licenses under the Civil Rights Act of 1964. Most were rejected, with racing officials claiming women were unfit to ride, and those who tried faced boycotts from male jockeys. At just 20 years old, […]
Feb 05
5:00 pm - 7:00 pm
National Sporting Library & Museum
102 The Plains Rd, Middleburg, VA 20117
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Winter Pairing Dinner

You’re invited to an intimate food pairing dinner in Lost Barrel’s cozy loft, featuring a curated five-course menu by Executive Chef Jose. Each course is thoughtfully paired with a Lost Barrel beer or cocktail, selected to enhance and complement every dish. Throughout the evening, Head Brewer Dan will share insights into the brewing process and […]
Feb 06
6:00 pm - 9:00 pm
Lost Barrel Brewing
36138 John Mosby Hwy, Middleburg, VA 20117
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Lost Barrel’s Galentine’s Day Party & Market

Celebrate those who make life amazing! Grab your friends and join us for a fun-filled Galentine’s Day at Lost Barrel Brewing. Lost Barrel is bringing together local makers, boutique vendors, and unique experiential pop-ups! Shop, sip, laugh, and make memories at Lost Barrel! Bring your friends! Click here for more information.
Feb 07
12:00 am - 7:00 pm
Lost Barrel Brewing
36138 John Mosby Hwy, Middleburg, VA 20117
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Live Music with Robert Mabe & Friends

Join Lost Barrel Brewing for live music, drinks, food and fun! About this event: Lost Barrel Brewing is an all-ages brewery located in Middleburg, VA on a horse farm. We welcome you to enjoy the taproom, porch, stunning yard or private gathering spaces. The music will be indoors when cold and outdoors on the porch […]
Feb 07
4:00 am - 7:00 pm
Lost Barrel Brewing
36138 John Mosby Hwy, Middleburg, VA 20117
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Mini & Me Valentine’s Day

Join us for a heart-filled day designed for parents, grandparents, guardians, and their little ones! Our Mini & Me Valentine’s celebration is all about connection, creativity, and making sweet memories together. Explore a curated selection of local vendors along with hands-on stations where you and your mini can create something special—think crafts, keepsakes, and Valentine […]
Feb 08
12:00 pm - 4:00 pm
Lost Barrel Brewing
36138 John Mosby Hwy, Middleburg, VA 20117
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Fundraiser Bingo for Humane Society of Loudoun County

Join Lost Barrel Brewing once a month for Fundraiser Bingo, where fun meets community impact. Whether you are coming out to support the featured nonprofit or simply want to play a few rounds of bingo, everyone is welcome. Free to attend Lost Barrel Brewing donates 10 percent of all food sales during the event to […]
Feb 08
4:30 pm - 6:30 pm
Lost Barrel Brewing
36138 John Mosby Hwy, Middleburg, VA 20117
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Wine & Nine Enneagram

Love Better – Starting with Yourself. Valentine’s season isn’t just about romance—it’s about understanding, connection, and loving well in every relationship. Join me for a cozy, fun Enneagram evening where we’ll explore how personality shapes how we love, communicate, and relate—to partners, friends, family, and ourselves. Perfect whether you’re single, coupled, or “it’s complicated.” Wine, […]
Feb 09
6:00 pm - 8:00 pm
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