Middleburg has always been home to the horses-and-hounds set, but besides watching steeplechase and polo, day-trippers should focus on exploring the historic downtown district. This was Loudoun County’s commercial hub for centuries, and the town still has more than 100 eateries, shops, and art galleries. First lady Jacqueline Kennedy, an avid equestrian, brought the world’s attention to Middleburg when she purchased a 166-acre retreat in the 1960s, and President John F. Kennedy held numerous meetings and press conferences at the iconic Red Fox Inn & Tavern. When you visit, set aside enough time to savor Middleburg’s friendliness and the serenity of its countryside setting.
SIP
1. Sample the region’s premier cider and spirits at Mt. Defiance Cidery and Distillery. Along the way, you’ll learn about traditional cider-making, which harks back to the town’s colonial-era roots. 207 W. Washington St., Middleburg, mtdefiance.com
SHOP
2. Conversation ensues inside Brick and Mortar Mercantile, a warehouse filled with irreverent guy-friendly merchandise. Locally made food and beverage products sit beside portable record players, Shinola watches, and Stetson hats. 201 W. Washington St., Middleburg, justbrickandmortar.com
BROWSE
3. “If we don’t have it, you don’t need it,” is the motto of The Fun Shop, a Middleburg institution since 1956. The mini-department store sells party supplies, kitchenware, pet gear, toys, and garden decor. 117 W. Washington St., Middleburg, thefunshop.com
CAFFEINATE
4. Middleburg Common Grounds creates custom coffee drinks and luscious pastries. Track the street action from under a striped umbrella on the café’s cheerful patio. 114 W. Washington St., Middleburg, middleburgcommongrounds.com
TAILOR
5. Highcliffe Clothiers is an old-school haberdashery with posh apparel for men and women. The shopkeepers offer custom fitting and have expertise in everything from leather boots to tuxedos. 112 W. Washington St., Middleburg, highcliffeclothiers.com
SNIFF
6. The Eden-like gardens around Nature Composed necessitate inhaling deeply as you pass by. Find an enchanting planter for your home or porch here—the floral creations are arranged in pots, hanging baskets, and terrariums, offering up hypnotizing scents and wild beauty. 12 S. Pendleton St., Middleburg, naturecomposed.com
OUTFIT
7. Your four-legged friend will be the best-dressed in town when you shop at The Tack Box. Even if you don’t own a horse or dog, it’s fun to inspect the saddles, riding crops, velvet helmets, and plaid dog coats in this 60-year-old Middleburg establishment. 7 W. Federal St., Middleburg, thetackboxinc.com
TASTE
8. Best Thai Kitchen is a hidden gem. Across the street from Thaiverse Restaurant (also first-rate), you’ll find a low-key ambience and fresh ingredients. Dine on blazing-hot tom yum soup or the refreshing papaya salad. 4 E. Federal St., Middleburg, bestthaikitchen.com
SLURP
9. Don’t leave town without hitting happy hour. King Street Oyster Bar beckons with a host of tempting deals, like $1 oysters and $5 drinks, and is located inside a former bank building. 1 E. Washington St., Middleburg, kingstreetoysterbar.com
BUY
10. Browse the likes of AG Jeans and Free People at Zest Clothing & Co., another locally owned boutique. 9 E. Washington St., Middleburg, zestclothingandco.com
TRY ON
11. Chloe’s of Middleburg stocks trendy styles for women, including gilt-edged handbags, shoes, and dresses. 12 E. Washington St., Middleburg, chloesofmiddleburg.com
GLOW
12. Crème de la Crème is the ultimate in tasteful furnishings and keepsakes. The store’s signature ceramic candles will help you replicate that Middleburg elegance at home. 23 E. Washington St., shopcremedelacreme.com
This Month
Aug. 7, 14, 21 & 28: Watch ponies and riders compete at Twilight Polo at Great Meadow. Tickets required. twilightpolo.com
Aug. 14–22: World-class chefs and sommeliers are gathering at the Salamander Resort for Family Reunion, a series of cooking classes and demos, wine tastings, dinners, and panel discussions toasting diversity in the hospitality industry. Reservations required. salamanderhotels.com/familyreunion
Feature image courtesy National Sporting Library & Museum
This story originally ran in our August issue. For more stories like this, subscribe to our monthly magazine.
