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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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An Evening with Josh Pons, Author of Letters from Country Life: Adolphe Pons, Man O’ War, and the Founding of Maryland

Join the National Sporting Library & Museum for an evening with Josh Pons, author of Letters from Country Life: Adolphe Pons, Man O’ War, and the Founding of Maryland. A third generation horseman and owner of Country Life Farm, Pons shares a century inside the Thoroughbred world, told from Maryland’s oldest Thoroughbred farm. He is […]
Jan 15
5:00 pm - 7:00 pm
National Sporting Library & Museum
102 The Plains Rd, Middleburg, VA 20117
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Equine Education Program: The Ins and Outs of the Equine Digestive System

Horse owners often hear the basic rules of feeding forage first and offering small, frequent meals. But understanding how the horse’s digestive system actually works explains why these guidelines matter. Join Jessie Wade for an in depth look at the equine digestive system and learn why feeding practices that align with a horse’s natural design […]
Jan 17
2:00 pm - 3:00 pm
TriCounty Feeds
7408 John Marshall Hwy, The Plains, VA
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Live Music with 2 of the Four

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 on a horse farm. LBB welcomes you to enjoy our taproom, porch, stunning yard or private gathering spaces. The music will be indoors when cold and outdoors on the porch weather […]
Jan 17
4:00 pm - 7:00 pm
Lost Barrel Brewing
36138 John Mosby Hwy, Middleburg, VA 20117
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Adult 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 […]
Jan 17
5:00 pm - 7:30 pm
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Uncork Your Dreams – A Vision Workshop with DeeAnn Jeremiah

Life Coach DeeAnn Jeremiah will be leading a guided workshop that blends thoughtful reflection with the art of wine tasting. This experience invites participants to slow down, savor the moment, and clarify what truly matters next. Through facilitated discussion, visioning exercises, and curated wine selections, you’ll explore where you are, where you’re headed, and how […]
Jan 18
1:00 pm - 2:00 pm
Slater Run Vineyards
1500 Crenshaw Rd, Upperville, VA 20184
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America’s 250th Anniversary Kickoff Event

The Town of Middleburg invites the public to attend a community-wide kick-off event celebrating America’s 250th Anniversary. This special event will honor the nation’s history while launching a year-long commemoration of the 250th anniversary of the founding of the United States. The celebration will take place at the Middleburg Town Hall and the Middleburg Community […]
Jan 23
4:30 pm - 7:30 pm
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