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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
June 2026

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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Juneteenth Community Celebration

The Middleburg Library, Middleburg Community Center, and the Middleburg Museum are coming together for a pre‑Juneteenth program featuring “A Story of Hope & Freedom” presented by Kevin Dulany Grigsby. This collaborative event highlights the history, resilience, and legacy of the Proctors of Loudoun and Fauquier Counties, offering space for reflection, learning, and community connection. This […]
Jun 18
7:00 pm - 9:00 pm
Middleburg Community Center
300 W Washington St, Middleburg, VA 20117
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Adult Chamber Music Workshop

Adult Chamber Music Workshop June 19–21, 2026 from 10:00AM – 3:00PM Trinity Episcopal Church 9108 John S. Mosby Hwy, Upperville, VA Details: Open to all string and woodwind players – all levels welcome This inspiring three-day program is designed for adult musicians who want to reconnect with their instrument or deepen their ensemble experience. The […]
Jun 19 - 21
10:00 am - 3:00 pm
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1776 to Juneteenth Expanding Freedom

In celebration of Juneteenth, the Middleburg Museum will offer ten signed copies of “A Story of Hope & Freedom” and “A Path Through Willisville” during a special program in the Garden! The afternoon features an uplifting gospel performance, a short skit, an opera solo, and a keynote from a member of the Daughters of the […]
Jun 19
11:00 am - 2:00 pm
The Middleburg Museum
8 North Madison Street, Middleburg, VA 20117
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Rosé Brunch in Wine Country

Get ready for a chill and fun in-person brunch! Explore a tasting menu of four Cana Vineyards Rosés while enjoying tasty brunch bites and great company. It’s the perfect way to spend a summer weekend with friends, all in a relaxed setting. Don’t miss out on this rosé-filled good time! On the Wine List: 2025 […]
Jun 20
11:00 am - 1:00 pm
Cana Vineyards & Winery
38600 Little River Turnpike, Middleburg, VA 20117
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Juneteenth Block Party

Join the Town of Middleburg and the Middleburg Police Department at Middleburg Community Center for a Juneteenth Block Party! Free concert with Bryan Fox & Friends, pizza, food, and ice cream! Free face painting and swim at the pool! Enjoy special guest speakers and support local black-owned vendors! Click here to RSVP.
Jun 20
12:00 pm - 4:00 pm
Middleburg Community Center
300 W Washington St, Middleburg, VA 20117
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