Nestled among the rolling hills and winding country roads of Loudoun County lies the charming town of Middleburg. As the nation’s horse and hunt capital, this unassuming, sleepy town is fittingly reminiscent of the little villages that dot the British countryside. With its buildings constructed of fieldstone gathered just miles from the town, one could easily spend a day admiring Middleburg solely for its architectural beauty.
But for seasoned shoppers, Middleburg is perhaps one of Northern Virginia’s best-kept secrets.
Once a center for agricultural trade, today Middleburg is thrumming with tourists eager to poke their heads into one of the many quaint boutiques that sell everything from saddles to home goods and Christmas decorations.
Between the picturesque beauty and rich history, Middleburg is a must-see destination for shoppers and nature lovers alike. But don’t worry, you won’t need your jodhpurs for this day trip.
Middleburg Common Grounds
Start your day trip like a local with fresh brewed coffee and a pastry from Middleburg Common Grounds. Relax inside this cozy café as passersby stop in for their morning brew before heading to work, or sit on the streetside outdoor patio before hitting the pavement. 114 W. Washington St., Middleburg
Country Classics
Does your wardrobe need a refresh? Country Classics, a proprietary brand founded in 1989 by Diane Rigden, has everything you need to embrace your inner sartorial extrovert. Every garment sold at Country Classics is made exclusively for its shop by skilled craftsmen in the United Kingdom and Europe. 21 E. Washington St., Middleburg
Middleburg Books
Discover your next page-turning thriller or steamy romance novel at one of Middleburg’s newest additions, Middleburg Books. Before its September grand opening, this independent bookshop in the heart of town underwent substantial renovation, exposing wood beams that date back to the building’s original construction in 1750. Proprietor Mary Beth Morell, a former school librarian, opened the shop alongside co-founder and self-professed book nerd Christina Duffy to inspire change through stories that move readers. Choose from a selection of fiction, non-fiction, and children’s books. 17 S. Madison St., Middleburg
Red Fox Inn and Tavern
Frequented by President John F. Kennedy and Jacqueline Kennedy Onassis, the Red Fox Inn and Tavern is one of the oldest continuously operating inns in the United States. Established in 1728 by John Chinn, the Red Fox was built from local fieldstone, and, on occasion, Chinn’s cousin, an industrious surveyor by the name of George Washington, would drop by. Today, the Red Fox Inn and Tavern maintains its colonial theme with a distinctly modern twist — the perfect spot for a boutique sojourn in style or a hearty pub meal by the hearth. 2 E. Washington St., Middleburg
Tully Rector
From eclectic accessories to trendy mainstays, Tully Rector offers a carefully curated selection of quality women’s clothing and home goods that cater to every style and sensibility. Find everything you need to look and feel your best this season. 7 E. Washington St., Middleburg
Middleburg Antique Gallery
A day trip to Middleburg wouldn’t be complete without stopping at Middleburg Antique Gallery. Owner Linda Mason sources premium antiques from across the globe, specializing in pieces from the 18th, 19th, and 20th centuries. Don’t be afraid to get lost as history comes alive in this cornucopia of antique goods. 107 W. Washington St., Middleburg
PLAYroom
Are you looking for high-quality, sustainable toys for your little ones? As a mom herself, founder Michelle McNaughton understands the importance of toys that not only entertain, but also stand the test of time. That’s why the PLAYroom is dedicated to sourcing only the best, heirloom-quality toys that encourage imagination and open-ended play for kids between the ages of 2 and 10. Whether you’re looking for wooden blocks, plush animals, or educational games, you’ll find it all here. Explore the PLAYroom and let your child’s imagination run wild. 108 W. Washington St., Middleburg
Brick and Mortar Mercantile
At Brick and Mortar Mercantile, you’ll find no shortage of gags, trinkets, and tongue-in-cheek curiosities that will keep your family laughing for the whole year. Founded on the belief that you should enjoy shopping, Brick and Mortar Mercantile selects products that you won’t find online. 201 W. Washington St., Middleburg
Tremolo Bar
Take a break from shopping at this brainchild of veteran restauranteur Jarad Slipp. Tremolo’s menu consists of exquisite light bites, craft coffee, and elevated cocktails stripped bare of their usual pretentiousness. Slipp, a master sommelier, has an impressive resume, with stints at renowned restaurants like the Michelin one-star Casa Vissani in Italy, CityZen in DC, and Restaurant Gordon Ramsay in London, which has three Michelin stars. At Tremolo Bar, guests can expect a refined meal in elegant environs paired with an outstanding glass of wine or a classic cocktail. 19 E. Washington St., Middleburg
Crème de la Crème
Spruce up your home décor or fall in love with something new. Choose from a wide-ranging selection of home and paper goods that pairs French and Italian living with Southern hospitality. 23 E. Washington St., Middleburg
Mt. Defiance Cidery and Distillery
After a long day of shopping in Middleburg, take a load off at the award-winning Mt. Defiance Cidery and Distillery. With two locations to choose from, conveniently located on either side of Middleburg’s main strip, you can recline while sipping housemade cider and spirits. The Cider Barn location expertly crafts alcoholic cider from Virginia apples, while the distillery site distills and ages everything from absinthe and amaretto to apple brandy and whiskey. 207 W. Washington St. and 495 E. Washington St., Middleburg
Feature image by Bennett Freeze
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