The Best Things To Do In Middleburg, Virginia

The drive to Middleburg, Virginia, from Washington, D.C., takes a little over an hour, but it feels like entering an entirely different world. As you travel away from the sprawl of the city and toward the mountains, the route eventually veers off the highway and onto a two-lane road, which passes bucolic fields, rambling stone walls, and grazing cows.

This small retreat town on the edge of the Virginia Piedmont has long served as a detox from being in the thick of things. Historically, Middleburg has been the place where the D.C. elite came to decompress from their daily lives. It’s close enough to the District that visitors could quickly get back to work or home in a pinch, but far enough away that it feels like an escape from the city. Jack and Jackie Kennedy had a home here, as did Elizabeth Taylor and her sixth husband, Senator John Warner.

The first thing that greets you upon entering the town are signs for the National Sporting Library and Museum (“sporting” here means hobbies like hunting and steeplechasing). Middleburg is known as a hub for these kinds of horse-centered hobbies, but the town has more to offer than just equine adventures. If you’re looking for an idyllic weekend getaway where you can meander in a tiny town, feel glamorous, and bring your dog, Middleburg is the place to go.  

Where to Shop

You could spend an entire day browsing Middleburg's charming boutiques. Suitable for shopping with the whole family, Brick & Mortar Mercantile offers a range of locally-made and locally-themed items ranging from candles to mugs, coasters, and towels printed with funny—and a little risque—phrases. (The shop's Campfire Mug reads "Definitely not coffee.") It’s also the home of parakeets Brick & Mortar, after whom the store is named.

For kitchen decor and gadgets and other high-end home goods, head to The Fun Shop, which lives up to its name. Les Jardins De Bagatelle stocks an exquisite selection of French imports. For stylish homes, Atelier Design & Decor offers textiles and fixtures that will charm guests and serve as tasteful statement pieces. Garden enthusiasts will enjoy the two-for-one plant and design offerings at Nature Composed and the adjacent restaurant Provender, which bills itself as "a garden kitchen."

An added bonus: almost all of these shops are either dog-friendly or have a shop dog ready to greet you upon entrance. 

Kids and fur-babies can find treats, too–the PLAYroom is an old-fashioned toy store full of educational and fun items. Nearby is Loyal Companion, which offers everything from toys to health food for your dog. Across the street from Loyal Companion is Chloe’s, a clothing and gift store that also carries high-end gifts for fancy pups. And just up the block is Scruffy’s Ice Cream Parlor, serving street-side cones and specialty coffees with seasonal flavors. 

For statement pieces with storied histories, the town is packed with shops sure to wow the serious antique hunter. Nearly every block downtown has one. Favorites include the Middletown Antique Emporium and Creme de la Creme.

Where to Eat

When you need a break from shopping, Knead Wine, a new wine and pizza shop, is a perfect spot for a midday bite. Knead offers take-out artisan pizza and a carefully curated selection of wine ($20 bottles on one side of the shop, $45 bottles on the other).

For a more leisurely sit-down experience, locals recommended Tremolo, a wine bar with small plates. The bustling King Street Oyster Bar is also not to be missed, especially for $7 happy hour specials. Other options include the quiet and historic Red Fox Tavern, which offers a prix fixe menu, and Red Horse Tavern, which serves classic pub fare.

Where to Drink

Middleburg sits in the northern Virginia Piedmont, which is an AVA-designated region prime for growing wine grapes. The combination of this microclimate and the wealth accumulated in the Middleburg community means that there are a variety of lovely wineries nearby if you want to do a tasting crawl. Check out Greenhill Winery, Cana Vineyards, and Boxwood Winery (just to name a few).

For the non-oenophile, Mt. Defiance Distillery & Cidery offers a wide selection of spirits and local ciders and has outdoor seating with a nice view of downtown. 

Where to Stay

Treat yourself to a day of pampering at Salamander Resort and Spa. The rambling 340-acre property, owned by Sheila Johnson, co-founder of BET, sits just outside of town and offers amenities including an equestrian center, indoor and outdoor pools, and tennis courts, in addition to a full-service spa. The resort's restaurant, Harrimans Virginia Piedmont Grill, offers a seasonally-changing menu that includes local produce and meat.

For an elegant in-town stay that wont break the bank, the Red Fox Inn offers a historic experience right in the heart of downtown Middleburg.