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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
May 2026

“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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June 2026

Garden Dialogues

Discover three exceptional, rural retreats, where the pastoral landscape of the greater Washington, D.C., metropolitan area—historically farmland—meets innovative, modern design in Leesburg, VA. Curated by Jennifer Horn, founding Principal of Jennifer Horn & Company, this exclusive tour stops at three separate sites, each designed by a different, leading D.C.-based firm, including Moody Graham Landscape Architecture […]
Jun 13
11:00 am - 2:00 pm
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Imagine Life Coaching Middleburg Retreat

Imagine Life Coaching invites you to a restorative day focused on reflection, renewal, and personal alignment. This gathering at 22865 Foxcroft Rd offers a peaceful setting for connection and growth. Through mindful practices, creative exploration, and time in nature, attendees will support their well‑being during this season of transition. The day includes an Enneagram discovery […]
Jun 14
9:00 am - 3:30 pm
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Hops for Hope: Event for National Center for Missing & Exploited Children

Join Lost Barrel Brewing for an afternoon of cold beer, live music, and shared purpose in support of the National Center for Missing and Exploited Children (NCMEC). Guests can enjoy live music from Steve Boyd and Friends from 4 to 7 pm, with the taproom remaining open until 8 pm Lost Barrel Brewing will make […]
Jun 14
3:00 pm - 7:00 pm
Lost Barrel Brewing
36138 John Mosby Hwy, Middleburg, VA 20117
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Tour Tuesdays at Foxcroft!

Foxcroft School invites friends and prospective families to Tour Tuesdays, an in‑person opportunity to experience campus life firsthand. Visitors will enjoy a student‑guided walk across the school’s 500‑acre campus, meet community leaders and educators, and share a relaxed “summer camp” lunch in the dining hall. Visitors may also explore the equestrian facilities (if interested), take […]
Jun 16
All Day
Foxcroft School
22407 Foxhound Lane Middleburg VA
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