This Is The Friendliest Small Town In Virginia
Middleburg is a small town in Virginia, known for an equestrian culture that routinely brings people together throughout the year. While fewer than 1,000 people call Middleburg home, the Virginia Fall Races draws over 10,000 fans to cheer on the horses and enjoy the festivities. Downtown, spots like Nomad run tastings for guests working through the bourbon menu. Despite its small population, Middleburg has a full calendar of year-round events, helping it earn the title of the friendliest small town in Virginia.
Middleburg's Equestrian Heritage
Middleburg has long been regarded as a premier destination for equestrian sport, so much so that it is often referred to as America's Horse and Hunt Country Capital. The National Sporting Library and Museum is a 6-acre campus combining a research library and a fine art museum that highlights the area's heritage. Exhibits cover subjects like horsemanship, foxhunting, and wildlife, and the museum hosts educational programs, rotating exhibitions, and family activities throughout the year.
Equestrian events are held annually in Middleburg at Glenwood Park, Virginia's oldest continuous steeplechase course. The Middleburg Spring Races are held each April. Visitors can set up chairs and blankets to watch the most athletic thoroughbreds in the nation compete. In between races, horses are viewable from a holding paddock, vendors line the grounds, and food trucks keep attendees fed.
Each October, equestrian enthusiasts return to Glenwood Park for the Virginia Fall Races. In addition to more steeplechase action, visitors also enjoy the Family Fun Fair, which has something for people of all ages. Children have access to a petting zoo and a bounce house, while adults wander the booths at Vendor Village, which showcases everything from clothing to handcrafted artisanal goods.
Downtown Middleburg
More consistent events in Middleburg include the Middleburg Community Farmer's Market, held from the first Saturday in May to the last Saturday in October. The parking lot of Middleburg Town Hall fills with vendors offering fresh produce, baked goods, teas, eggs, and more. Most Saturdays feature food trucks and live music on site.
Nomad has a rustic interior of wooden paneling, brickwork, and leather booths, with cocktails built to pair with the menu's small plates. The bourbon list runs deep, with a wide selection of rare, aged, and small-batch pours.
The Red Fox Inn and Tavern is housed inside a historic 1728 tavern in the center of town. Locals and visitors come to enjoy breakfast, brunch, and dinner inside the rustic tavern furnished with oak tables, a stone fireplace, and exposed ceiling beams. The Night Fox Pub is on the second floor of the tavern with a more laid-back atmosphere.
Elevated Hospitality
Lost Barrel Brewing is a craft brewery on a 76-acre horse farm that produces its beers, hard seltzers, and food in-house. Indoor taproom seating, a porch, and picnic grounds all work for larger groups. Live music runs Fridays, Saturdays, and Sundays, with views of the farm and horses from most seats.
Salamander Middleburg sits on the edge of town on roughly 340 acres. The resort includes a 23,000-square-foot spa with 14 treatment rooms, a heated outdoor pool, and an equestrian center with a 25,000-square-foot riding arena. On-site dining at Harrimans Virginia Piedmont Grill runs to butcher's cuts, seafood, and full desserts.
Other Festivals
Middleburg has more to offer than all things equestrian. Since 2013, the Middleburg Film Festival has taken place over four days each October. During those four days, dozens of narrative and documentary films are screened at the Salamander Middleburg as well as at various downtown locations. Screenings are followed by conversations with directors, actors, and other special guests.
Christmas in Middleburg is a much-anticipated festival that takes place on the first Saturday of December and has been held for more than 50 years. The most well-known aspect of the festival is the mile-long parade, which features riders and horses dressed in formal riding attire herding a group of foxhounds down the street, paying homage to the town's fox hunting and equestrian roots. Other sights to behold around town during the festival include Christmas light displays and a window-decorating contest among participating local businesses.
Virginia's Friendliest Town
Middleburg's friendliness stems from how its small community routinely comes together to celebrate its heritage and traditions. The equestrian culture runs through many of the festivals and through local fixtures like Lost Barrel Brewing, but the welcome carries beyond the horse circuit. The Red Fox Inn and Tavern has been hosting travelers since 1728, and newer arrivals like Nomad have settled into the same rhythm. Whatever the reason for visiting, the reception tends to feel consistent.
