Nestled in lush Blue Ridge foothills, this gorgeous Piedmont town dates back to 1728 when a fieldstone tavern – today’s boutique Red Fox Inn – was established by a cousin of George Washington. Hailed as the nation’s Horse and Hunt Capital, its picture-perfect downtown is lined with country-chic boutiques, gourmet cafés, farm-to-fork restaurants and galleries, while the surrounding land is a dreamscape of historic mansions, elegant wineries, craft breweries and horse farms


The town’s National Sporting Library and Museum is the nation’s leading resource on equestrian and outdoor pursuits. Each December horses and hounds lead the glittering Christmas in Middleburg parade through town. On the northern outskirts, equestrian-themed Salamander Middleburg hosts the annual Family Reunion food and wine festival that celebrates diversity in the hospitality community as well as the star-studded Middleburg Film Festival, a major stop on the Oscar trail. See for yourself why Jackie Kennedy and Liz Taylor frequently visited the town.



Must Do:

Pamper Yourself

The Salamander Resort & Spa in rolling countryside just outside town is a luxurious equine-themed resort with a state-of-the-art spa, cozy lounge and dining areas, and multiple sporting activities. The equally enchanting Goodstone Inn & Restaurant, on 265-acres, features 18 guest rooms, trails, spa services and a superb tasting menu in its fine dining Conservatory restaurant.



Horse Around

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 draws a tony crowd each April to steeplechase events at Glenwood Park, and the new Masters of the Foxhounds Museum is dedicated to Middleburg’s favorite sport - foxhunting.



Dine Around

An outpost of Leesburg’s King Street Oyster Bar occupies the cavernous old bank building downtown (try the oysters and tuna taco), while the Red Fox Inn across the street does modern southern dishes with fresh Piedmont ingredients. Try the crab cakes and sweetcorn polenta. Nearby Thaiverse and Red Bar Sushi bring some Asian spice.



Get in the Spirit

Mt Defiance Cidery & Distillery is praised for its handcrafted small-batch cider and classic spirits – rums, bourbon, vermouth and even a potent absinthe. They now have two locations, one just out of town.




Middleburg’s vintners are upping Loudoun’s wine game. Modish Greenhill Winery & Vineyard’s Blanc de Blancs was included in the 2016 Academy Awards gift bag, while the sleek Boxwood Winery does lush, velvety Bordeaux blends. Chrysalis Vineyards at The Ag District, on a hilltop outside town, specializes in Norton grape varietals and also sells local cheese, jams and charcuterie. Cana Vineyards 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 Boutiques. The nearby Fun Shop and Christmas Sleigh sell hunt country accessories and home décor.



Coffee & Cake

Refuel with a cup of joe at local coffee bars Cuppa Giddy Up or Middleburg Common Grounds, try the fresh baked goods at Upper Crust, or grab a sandwich, salad, soup and coffee at Market Salamander down the street.



Beer Crawl

Middleburg is blessed with the innovative Lost Barrel Brewing west of town which has a sleek taproom, wide porch and lawn dotted with Adirondacks and firepits around which to sip handcrafted ale, lager and hard seltzer.



Not to Miss Events

Middleburg Film Festival, October

This popular celebration of the best in cinema returns to a fully in-person event this fall from October 14-17.  Filmgoers from all over the world come to see Oscar-bound favorites and while red carpet stars often attend, the festival takes place in a relaxed, friendly and casual atmosphere.


Christmas in Middleburg, December

This beloved 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, Harley riders, hunt dogs and farm animals. Festive fun for all the family.


Middleburg Spring Races, April

Glenwood Park north of Middleburg hosts this flagship event on the Loudoun social calendar, as synonymous with the season as dogwoods and daffodils. Based on the original fox hunt point-to-point meets dating back to 1911, join race aficionados and designer-dressed fans as they tailgate and cheer on some of the fastest hurdle horses in the world.


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.