Discover Middleburg, Virginia

Discover Middleburg, Virginia

  • Horse Farms & Country Homes
  • 05/8/24

As real estate agents specializing in the beautiful region of Middleburg, VA, we're excited to give you the insider’s scoop on all the engaging activities and events this charming town offers. Known for its rich history, deep-rooted equestrian culture, and vibrant community life, Middleburg is a destination that delights residents and visitors alike. Whether you’re considering moving here or just visiting, there's always something to do in Middleburg that connects you with its unique lifestyle.

Equestrian Events: The Heartbeat of Middleburg

Middleburg is synonymous with equestrian activities, hosting several high-profile horse-related events throughout the year that draw crowds from across the nation.

Point-to-Point and Steeplechase Schedule

Middleburg’s spring and fall seasons are marked by the thrilling point-to-point and steeplechase races. These events are a fantastic way to experience the tradition of American horse racing, with the Middleburg Spring Races and the Virginia Fall Races being particular highlights. These races not only offer exciting competition but also provide a great social atmosphere.

Sunset Polo at Great Meadow in The Plains

Every Saturday night during the summer, the Great Meadow in The Plains hosts Sunset Polo. This event is perfect for a family outing or a romantic evening under the stars, featuring three fast-paced polo matches, halftime entertainment, and plenty of space to picnic.

Twilight Jumpers

For those who prefer show jumping, Twilight Jumpers are held on select evenings throughout the summer. This event combines top-notch equestrian competition with a relaxed, social environment perfect for end-of-day relaxation.

Upperville Horse Show

Dating back to 1853, the Upperville Colt & Horse Show is the oldest horse show in America. Taking place every June, this week-long event showcases some of the best horses and riders in the country competing across different classes and disciplines.

Community and Cultural Events: The Soul of Middleburg

Middleburg is not only about horse racing; it's a hub of community and cultural activities that enrich the local lifestyle. The Middleburg Community Center is at the core of local life, offering a variety of events year-round. From summer concerts and outdoor movie nights to educational programs and fitness classes, the community center provides something for everyone, fostering a tight-knit community spirit.

The National Sporting Library & Museum is a must-visit for history buffs and sporting enthusiasts. This facility is dedicated to preserving, promoting, and sharing the literature, art, and culture of horse sports and field sports, offering an insightful look into the traditional sporting life.

The Middleburg Film Festival is an annual celebration of independent film over four days in October. Since its inception in 2013, the festival has rapidly grown in prestige and popularity, attracting filmmakers, critics, and movie enthusiasts worldwide. Screenings and events are held at various venues throughout the picturesque town of Middleburg, including Salamander Resort & Spa, which serves as the festival’s hub. Other venues include local theaters, community centers, and outdoor settings, offering a scenic backdrop to the film presentations.

Local Markets and Shopping

Middleburg’s shopping scene reflects its colonial past with modern flair, offering everything from boutiques selling equestrian gear to antique shops and local artisan goods.

  • Middleburg’s Farmers Market: From May through October, the market offers fresh local produce, meats, and handmade crafts. It’s a perfect spot to enjoy the local flavors and mingle with residents.
  • Downtown Shopping: Wander down historic Washington Street to explore a variety of shops that offer unique clothing, gifts, and art perfect for taking a piece of Middleburg home with you.

Outdoor Activities

The area around Middleburg is a haven for outdoor enthusiasts, with plenty of opportunities to enjoy the natural landscape.

  • Hiking and Biking: The nearby Blue Ridge Mountains and the Shenandoah Valley provide numerous trails for all levels of hikers and bikers.
  • Vineyard Tours: Middleburg is part of Virginia Wine Country, and a tour of local vineyards is a must. Visit Chrysalis Vineyards, Boxwood Winery, or Greenhill Winery & Vineyards to sample some of the best local wines.

Unique and Seasonal Activities: Middleburg’s Year-Round Charm

Mille Miglia Car Race

Inspired by the famous Italian road race, the Mille Miglia Storica, Middleburg, hosts an annual car event that features vintage sports cars from around the world. This is a spectacular event for car enthusiasts and offers a picturesque backdrop of autumnal Middleburg.

Big Holiday Parade

The Middleburg Christmas Parade is a cherished annual tradition, signaling the start of the holiday season. Featuring a unique blend of floats, bands, and horses, it captures Middleburg's festive spirit and community pride.

Whether you’re drawn to the thrill of equestrian sports, the calm of pastoral landscapes, or the warmth of community events, Middleburg offers an engaging blend of activities that make it an ideal place to live or visit. Our role as realtors is not just to sell homes, but to introduce you to a community where life is enriched with tradition, nature, and a vibrant social calendar. Middleburg is a place where every season offers new experiences and lasting memories. If you’re considering a move to Middleburg, you’re not just buying a property; you’re becoming part of a lively and loving community that will feel like home instantly.

If you need further information on the specifics of any event or have more questions about the lifestyle in Middleburg, feel free to reach out to Horse Farms & Country Homes—your Middleburg, Virginia, real estate experts. We're here to help you discover the perfect home and community that fits your lifestyle!

*Header photo courtesy of Horse Farms & Country Homes

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