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.
ALL YEAR EVENTS
SPRING EVENTS
Middleburg Hunt Point to Point
April 26, 2026
The Middleburg Hunt Point to Point Races at Glenwood Park offer a classic spring day in Virginia hunt country, featuring thrilling steeplechase racing, beautiful countryside views, and a lively social atmosphere.
36800 Glenwood Park Lane, Middleburg, VA 20117
SUMMER EVENTS
Four Nations Cup International Polo Tournament
Sunday, June 14, 2026
Teams from the United States and three invited nations compete across 12 thrilling chukkers, highlighting world-class skill, strategy, and the enduring partnership between horse and rider.
Grass Polo Field at Great Meadow
5089 Old Tavern Road, The Plains, VA 20176
A Tour of the Garden and Gallery at Oak Spring Garden
June 27th, 2025
Take a self-paced walking tour through the marvelous landscape in Upperville, Virginia. Selections from “Fantastic Flora” a digital educational exhibit that blends art, culture, history, and science to explore the role of plants in both human history and the natural world will be featured.
4884 Sea Hero Lane Upperville, VA 20184
AUTUMN EVENTS
Piedmont Jumper Classic
September 2025
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 24, 2026
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
Byrne Gallery Yuri Gorbachev Exhibit
Nov 04 2025 – Dec 30 2025
The Byrne Gallery proudly announces its 30th Anniversary and will mark the occasion with a special exhibition this November and December featuring the vibrant oil and enamel paintings of internationally renowned artist Yuri Gorbachev.
This will be Gorbachev’s 22nd consecutive show with the gallery. Highlights include selected works from his 2025 world museum tour. With a career spanning over 50 years and exhibitions across the globe, Gorbachev returns once again to Middleburg to help celebrate this milestone.
7 W Washington St, Middleburg, VA 20117
5th Annual Celebrating the Harvest
November 2025
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
WINTER EVENTS
A Dickens of a Dog Parade
December 13, 2025
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
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!
