The Best Things To Do In Sperryville, Virginia

Many people come to Sperryville as a way in and out of Shenandoah National Park—perhaps seeing it as an exit ramp, albeit naturally beautiful exit ramp, rather than as a destination unto itself. But the tiny, blink-and-you-miss-it town, packs a punch for those who choose to stay for the day rather than just pass through, or, better yet, set their sights on the town as a destination unto itself. 

Sperryville is a jumping off point for the wealth of the Shenandoah’s outdoor glories and hums with restaurants so good their reputations travel far beyond the lips the town’s population of just 291. It’s also here that you’ll find a slew of Virginia’s wineries and can dip your toes into the northern end of the South’s great distilling legacy. Just under two hours from Washington, DC, and touching the Skyline Drive, Sperryville is begging to be explored. 

What To Do

Hit The Trails

Whether you want a short meander into nature or are looking for an all-day adventure, there are endless hiking possibilities in and around Sperryville and trails for hikers of all interests and ambitions. For those looking to properly earn their dinner, the Hazel River Trailhead offers a challenging 12.7 out-and-back trail, and the 7.5 mile Little Devil Stairs Loop rewards climbers with several waterfalls and sweeping vistas. Right off Sperryville’s main street (the Sperryville Pike), the Rappahannock Walking Trail is a good option for those looking for a stroll rather than a sweat. 

Go For A Scenic Drive

For those looking for something a little more languid that still doesn’t skimp on the views, there is nothing better than a slow sojourn on the Skyline Drive. 105-miles in total, the iconic drive winds its way through the Shenandoah National Park with overlooks at the more scenic curves looking out on the Blue Ridge Mountains and the Shenandoah Valley. Enter or exit at Sperryville and make time for pictures or a picnic at Hazel Mountain Overlook and Thornton Hollow Overlook.

Sample Local Libations

Virginia’s wine business accounts for a staggering $5 billion. But what’s more, besides their blends and pours, the wineries around Sperryville draw in visitors and locals alike for their vineyards with views. While in Sperryville, make time for Quièvremont Vineyard & Winery, Glen Manor Vineyards, and the slightly further away (about a 25 minute drive) Chester Gap Cellars. For those less wine inclined, visits to Pen Druid Fermentation, which makes native beers and natural ciders, and Copper Fox Distillery, which concocts bourbons, brandies, and ryes, are musts

Shop The Best Of The Shenandoah Valley

Sperryville’s compact Corner Store is what small town dreams are made of. Stop in for local produce, fresh breads, pies, and quiches, and an expertly curated selection of wines from Virginia and beyond. For a larger selection of in-season produce, head to Waterpenny Farm, which has been growing and selling organic produce for over twenty years. Possum’s Store Art and Artisan Gallery (a 20-minute drive away) is a must for anyone looking for unique hand-crafted pieces. Occupying the space of the former 19th century general store, Possum’s peddles the wares from talented local artists and makers.

Where To Eat

Planning a memorable meal while in Sperryville is an activity that should not be taken for granted. Even if Sperryville were ten times its size, its dining options would be impressive. 

There is nothing quite to rewarding following a long Shenandoah hike as a celebratory cocktail at FRANCIS and a pie Rappahannock Pizza Kitchen, both of which are next to the Corner Store. But you don’t have to stay in that building for a great meal. 

A few buildings down you’ll find The Three Blacksmiths, a twenty-seat husband-and-wife run restaurant that serves a fixed menu of local and seasonal dishes in a candlelit space. Thanks to its size and ardent following, getting a reservation here can be tricky but check for last-minute availability. 

Five minutes down the road you’ll find the Restaurant at Blue Rock where its four-course tasting menu by Bin Lu, formerly of Washington, D.C.’s much-lauded restaurant, Pineapple & Pears, is paired with local and international wines. Patrick O’Connell three Michelin starred restaurant at the Inn at Little Washington is just down the road as well.

Where To Stay

Perhaps the most well-known place to stay in the area is The Inn at Little Washington, which is about a five-minute drive away from Sperryville’s Main Street. A stay here is nothing short of legendary, but if the price tag punches too high, Blue Rock, a genteel and modern take on a country inn, located on eighty acres of vineyards and rolling hills might just be the ticket. For charming B&B options right in town, try Hopkins Ordinary and The Inn at Mount Vernon Farm.