Can't Miss Annual Events in and around Middleburg, VA

Middleburg, Virginia, nestled in the heart of horse country, is rich in history, charm, and a vibrant equestrian culture. Every year, Middleburg and its surrounding areas host various events that draw visitors from near and far. Whether you're a resident or planning a visit, these annual events are not to be missed. From exhilarating horse races to charming holiday parades, there's something for everyone to enjoy. And if you're considering making Middleburg your home, Cindy Polk and Brandy Greenwell of Horse Farms & Country Homes are the perfect real estate agents to guide you through the process.

Kicking off the spring season, the Middleburg Spring Races at Glenwood Park are a highlight for equestrian enthusiasts. Held every April, this event showcases steeplechase racing at its finest. The races, a tradition since 1911, offer a thrilling day of sport and socializing. Visitors can enjoy tailgating, picnicking, and the excitement of watching the horses and jockeys compete. The picturesque setting of Glenwood Park adds to the allure, making it a perfect outing for families and friends.

Just a short drive from Middleburg, the Virginia Gold Cup at Great Meadows is another must-attend event. Taking place on the first Saturday in May, the Virginia Gold Cup is one of the premier steeplechase races in the country. With a history dating back to 1922, this event attracts tens of thousands of spectators who witness the thrilling races and participate in the lively festivities. From elaborate tailgate parties to fashionable attire, the Virginia Gold Cup is a quintessential part of Virginia's equestrian culture.

For those with a green thumb, the annual Blandy Farm Mother’s Day weekend plant sale is a delightful event. Held at the State Arboretum of Virginia, this plant sale features a wide variety of plants, including native species, perennials, herbs, and shrubs. It's the perfect opportunity to find unique plants for your garden while supporting the arboretum's educational and conservation programs. The event also offers gardening advice and demonstrations, making it a fun and informative outing for the whole family.

As the oldest horse show in the United States, the Upperville Colt and Horse Show is a prestigious event that attracts top competitors from around the world. Held every June, this week-long show features a range of equestrian disciplines, including hunter, jumper, and breeding classes. The showgrounds' historic oaks and charming atmosphere provide a stunning backdrop for the competition. In addition to the horse show, visitors can enjoy shopping, food vendors, and special exhibitions.

For a unique and exciting experience, don't miss Sunset Polo at Great Meadows. Held on select Fridays during the summer, this event combines the elegance of polo with a relaxed, family-friendly atmosphere. Spectators can enjoy the fast-paced action of polo matches while picnicking on the lawn and taking in the beautiful sunset over the Virginia countryside. It's a perfect way to spend a summer evening with friends and family.

Another equestrian event that draws crowds to Great Meadows is Twilight Jumpers. Held on select Fridays during the summer, this event features thrilling show-jumping competitions under the stars. With live music, food trucks, and a festive atmosphere, Twilight Jumpers is a fun and exciting way to experience the sport of show jumping. Whether you're a seasoned equestrian or a newcomer to the sport, you'll be captivated by the skill and athleticism of the horses and riders.

For a taste of traditional country fun, the Clarke County Fair is a must-visit. Held in August, this week-long fair offers a variety of attractions, including carnival rides, livestock shows, agricultural exhibits, and live entertainment. Visitors can enjoy delicious fair food, watch tractor pulls, and cheer on their favorite contestants in the demolition derby. The Clarke County Fair is a beloved event celebrating the area's rural heritage and providing fun for all ages.

Every October, film enthusiasts flock to the Middleburg Film Festival to enjoy a curated selection of films from around the world. This four-day event features screenings of narrative and documentary films, Q&A sessions with filmmakers, and special events such as wine tastings and panel discussions. The festival provides a unique opportunity to see award-winning films and discover new talent in the charming setting of Middleburg. It's a cultural highlight that attracts cinephiles and industry professionals alike.

Rounding out the year, the Middleburg Holiday Parade is a festive and heartwarming event that brings the community together to celebrate the holiday season. Held on the first Saturday in December, the parade features a procession of horse-drawn carriages, the local hunt with horses and hounds, and a variety of floats and marching bands. Santa Claus makes a special appearance, delighting children and adults alike. Holiday shopping, musical performances, and other festivities throughout the town follow the parade. It's a magical way to kick off the holiday season and experience the warmth and charm of Middleburg.

If you're captivated by Middleburg's charm and vibrant community and considering making it your home, Cindy Polk and Brandy Greenwell of Horse Farms & Country Homes are the ideal real estate agents to assist you. With their extensive knowledge of the local market and a passion for helping clients find their dream properties, Cindy and Brandy offer unparalleled service and expertise. Whether you're looking for a historic home, a horse farm, a country estate or a tract of land to build your dream home, they will guide you through every step of the process. 

In conclusion, Middleburg, VA, and its surrounding areas offer a rich tapestry of annual events that celebrate the region's equestrian heritage, agricultural roots, and vibrant community spirit. From the excitement of horse races and polo matches to the charm of holiday parades and film festivals, there's something for everyone to enjoy. Make sure to mark your calendar and experience these can't-miss events in Middleburg.