Middleburg

The National Sporting Library and Museum is the nation’s leading resource on equestrian and outdoor pursuits and has an exhibition space and fine art gallery. The Middleburg Spring Races and steeplechase events at Glenwood Park draw crowds each spring while the Masters of Foxhounds Museum is dedicated to the sport embedded in Middleburg’s history: foxhunting.

Middleburg’s vintners are upping Loudoun’s wine game. Modern, stylish Greenhill Vineyards’ Blanc de Blancs has been included in an Academy Awards gift bag, while the sleek Boxwood Estate Winery does lush, velvety Bordeaux blends. Chrysalis Vineyards at The Ag District, on a hilltop outside town, specializes in the Norton grape and also sells local cheese, jams and charcuterie. Cana Vineyards and Winery of Middleburg is overseen by brilliant female winemaker Melanie Natoli, while 50 West Vineyards is located high upon a bluff offering stunning views.

Washington Street is lined with classy boutiques and quirky gift stores. Pick up a tailored suit at Highcliffe Clothiers or a summery skirt at Lou Lou Boutique. The nearby Cèrme de la Crème features accessories and home décor while the Christmas Sleigh is a must-visit before the holidays.

• Middleburg Spring Races (April): Glenwood Park north of Middleburg hosts this flagship event, which is as synonymous with the season as dogwoods and daffodils. Rooted in the original fox hunt point-to-point meets dating back to 1911, the Middleburg Spring Races bring together race aficionados and designer-dressed fans to tailgate and cheer on some of the world’s fastest hurdle horses.
• Middleburg Summer Sidewalk Sale (August): Come out early to search for treasures from some of the most distinct boutiques and shops in Loudoun. Taking place the first weekend in August, shoppers can find unique bargains as vendors set out sale items on the traditional Middleburg brick sidewalks.
• Middleburg Film Festival (October): A major stop on the Oscar trail, the Middleburg Film Festival attracts film lovers from around the world to celebrate the best in cinema. While red carpet stars often attend, the festival takes place in a relaxed, friendly and casual atmosphere.
• Christmas in Middleburg (December): The spectacular Christmas in Middleburg parade takes place the first Saturday of December and features scarlet-jacketed riders on horseback, vintage horse-drawn carriages and a 1.5-mile procession of floats, drummers, bagpipers, bikers, hunt dogs and farm animals. Horses and hounds lead the glittering parade through town, and there’s festive fun for all the family.