Experience Middleburg
Middleburg and the surrounding Piedmont is home to some of the most unique activities and small businesses in the nation. Our established relationships with this hand selected list of local businesses will help you make the most of your time while staying with us. Read on to learn more about the many spectacular annual events and festivities that our region hosts, and please feel free to contact or visit our Inn Desk for additional advice and recommendations.
WINTER EVENTS
4th Annual Celebrating the Harvest
November 23, 2024
Join the Oak Spring Garden Foundation (OSGF) for a special evening as we gather around the table and celebrate the harvest through the seasons with a menu curated and created by Chef Jason Neve. Dishes will highlight a medley of heirloom crops grown at Oak Spring’s Biocultural Conservation Farm.
The Schoolhouse
8555 Mill Reef RoadMiddleburg, VA, 20117
2nd Annual Holiday Market in the Gallery
December 11, 2024 & December 12, 2024
Come enjoy the charms of the Oak Spring Garden Foundation’s Gallery and Gift Shop. Invited guests are welcome to drop in during our “open hours” for a shopping extravaganza just in time for the holiday season.
Oak Spring Garden Broodmare Barn
4884 Sea Hero Lane Upperville, VA 20117
A Dickens of a Dog Parade
December 21, 2024
Dress your pup in festive holiday attire and join the fun at Middleburg’s Dickens of a Dog Parade, where furry friends and their humans can strut their stuff and win exciting prizes!
National Sporting Library & Museum
102 The Plains Rd, Middleburg, VA 20117
AUTUMN EVENTS
Middleburg Oktoberfest
September 21, 2024
Join us for Middleburg’s 4th Oktoberfest, featuring two biergartens, local food, live music, and the new 2024 Corgi Races! Enjoy artwork from local artists, including fine art, pottery, jewelry, and more, available for purchase.
Middleburg
S. Madison and Federal Streets
NSLM Polo Classic
September 15, 2024
Proceeds from this Polo Classic benefit the National Sporting Library & Museum in its mission to preserve, promote, and share the literature, art, and culture of equestrian, angling, and field sports as well as advocate for the conservation of open space and waterways crucial to these sports.
Great Meadow
5089 Old Tavern Road, The Plains, VA 20198
Piedmont Jumper Classic
September 26 – September 29, 2024
Enjoy the excitement of the competition amidst the beauty of Upperville. This event brings together top riders and horses, showcasing the skill and precision of show jumping in Virginia’s horse country.
Salem Showgrounds
8300 Little River Tpke, Upperville, VA 20184
The Virginia Gold Cup Races
October 26, 2024
Celebrate the timeless tradition of steeplechase racing at the Virginia Gold Cup. Enjoy a thrilling day of competitive horse racing, tailgating, and fall festivities in the heart of Virginia’s countryside. Perfect for a day of outdoor fun and elegant gatherings.
Glenwood Park in Middleburg, Va
SPRING EVENTS
SUMMER EVENTS
More Resources
Curious to learn more? You can also go to the Visit Middleburg and Visit Loudoun websites for more events and happenings in the area!