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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
February 2026

Tri County Feed’s Equine Education Program: Feeding the Mare and Foal

Join TCF’s Jessie Wade for an informative seminar focused on the nutritional needs of broodmares and foals from pregnancy through weaning. Whether you’re preparing for a new foal or looking to refine your feeding program, this seminar offers valuable insights for setting mare and foal up for success. Click here for more info and to […]
Feb 21 - Mar 19
2:00 pm - 3:00 pm
TriCounty Feeds
7408 John Marshall Hwy, The Plains, VA
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Shrek the Musical

Shrek the Musical will be the largest production yet at Wakefield and the most ambitious show to take the stage in the GLO Theater since its opening four years ago. From expansive sets and dynamic lighting to bold makeup, detailed costumes, and a large, talented cast, every aspect of this production has been taken to […]
Feb 28
7:00 pm - 9:00 pm
Wakefield School
4339 Old Tavern Rd., The Plains, VA 20198
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March 2026

Shrek the Musical

Shrek the Musical will be the largest production yet at Wakefield and the most ambitious show to take the stage in the GLO Theater since its opening four years ago. From expansive sets and dynamic lighting to bold makeup, detailed costumes, and a large, talented cast, every aspect of this production has been taken to […]
Mar 01
2:30 pm - 3:30 pm
Wakefield School
4339 Old Tavern Rd., The Plains, VA 20198
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Blue Ridge Care’s FREE Webcast Watch Event

Blue Ridge Care is hosting a FREE watch event for the 2026 NACG National Webcast: Trauma-Responsive Grief Support for Youth & Families Impacted by Homicide. This powerful educational session features presenters from the Uplift Center for Grieving Children in Philadelphia and explores how historic and systemic oppression shape homicide-related grief experiences for youth and families. […]
Mar 03
1:00 pm - 4:30 pm
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Adventures Through Grief

Discover a unique approach to coping with grief through Blue Ridge Care’s FREE tabletop role playing game-based Adventures Through Grief program. Grief counselors act as game masters, guiding participants on a meaningful quest to navigate life after the death of someone significant to them. No prior role-playing game experience necessary. An application is required. Loudoun […]
Mar 03
5:45 pm - 7:45 pm
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Silhouettes by Erik

Erik is BACK! If you know, you know! Not only is this a truly beautiful piece of custom art and heirloom but to watch Erik work is nothing short of amazing! Erik will simply sit your child down and immediately start cutting your silhouette free had. You will watch him move his scissors deliberately and […]
Mar 04
2:00 pm - 5:00 pm
The PLAYroom
108 West Washington Street, Middleburg, VA 20117
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Tulip Mania at Oak Spring Garden Foundation Library

Join horticulturist and flower bulb grower Jason Delaney and the Oak Spring Garden Foundation Library staff for a richly illustrated and immersive lecture on the storied history of a timeless garden favorite, the tulip. Drawing from five centuries’ worth of lavish content in the OSGF Library’s rare and antiquarian holdings, Jason will enlighten participants on […]
Mar 05
3:30 am - 5:30 pm
Oak Spring Garden Foundation
1776 Loughborough Lane, Upperville, VA 20184
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