12 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 a 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 Shenandoah’s outdoor glories and hums with restaurants so good their reputations travel far beyond the lips of the town’s population of around 300. 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. Visit in the fall to experience the full autumn explosion of color in the Shenandoah Valley, or come in the spring to watch the town's annual rubber duck race.

Just under two hours from Washington, D.C., a little over an hour from Charlottesville, 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-mile out-and-back trail, and the 7.5-mile Little Devil Stairs Loop rewards climbers with several waterfalls and sweeping vistas. Other popular hikes include Mary's Rock Summit and Old Rag Mountain in Shenandoah National Park. 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. 

sperryfest.org

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. The iconic drive, 105 miles in total, 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.

nps.gov

nps.gov, Skyline Drive (mile 33.0)

skylinedriveoverlooks.com, Skyline Drive (mile 27.5)

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.

cornerstoresperryville.com, 3710 Sperryville Pike, Sperryville, VA 22740

waterpennyfarm.com, 53 Waterpenny Ln., Sperryville, VA 22740

Find Fresh Fruit At The Thorton River Orchard

A few miles west of Sperryville, Thorton River Orchard & Market is a must-stop for canned goods, local raw honey, and fresh seasonal fruits, like peaches, nectarines, and apples. In the fall, the orchard sells 24 varieties of apples, including Ambrosia, Candy Crisp, Nittany, Pink Lady, and more. 

thorntonriverorchard.com, 11587 Lee Hwy., Sperryville, VA 22740

Look For Art

Possum’s Store Art and Artisan Gallery (about 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. The venue also hosts workshops and small concerts.

possumsstoreva.com, 914 Old Blue Ridge Turnpike, Criglersville, VA 22727

Watch Rubber Ducks Race

Every April, locals and visitors alike race rubber ducks down the Thorton River during SperryFest in kids' and adults' dashes. The event doubles as a street festival on Main Street, with food, wine, artisans, and live entertainment like music, juggling, and more.

sperryfest.org

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. 

Drink And Eat At The Town's Corner Store

There is nothing quite too 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. 

bar-francis.com, 3710 Sperryville Pike, Sperryville, VA 22740

rappahannockpizzakitchen.com, 3710 Sperryville Pike, Sperryville, VA 22740

Don't Worry About Ordering

A few buildings down from the Corner Store, you’ll find The Three Blacksmiths, a 20-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. 

threeblacksmiths.com, 20 Main St., Sperryville, VA 22740

Try Fine Dining

Five minutes down the road from The Three Blacksmiths you’ll find the Restaurant at Blue Rock where its five-course tasting menu by Bin Lu, formerly of Washington, D.C.’s much-lauded restaurant, Pineapple & Pears, is paired with local and international wines.

bluerockva.com, 12567 Lee Hwy., Washington, VA 22747

Where To Drink

Sample The Local Wine

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 and the slightly further away (about a 25-minute drive) Chester Gap Cellars and (about a 45-minute drive) Glen Manor Vineyards,

quievremont.com, 162 Gidbrown Hollow Rd., Washington, VA 22747

glenmanorvineyards.com, 2244 Browntown Rd., Front Royal, VA 22630

chestergapcellars.com, 4615 Remount Rd., Front Royal, Virginia 22630

Kick Back With A Cider

For those less wine-inclined, a visit to Pen Druid Fermentation, which makes native beers and natural ciders as well as wine, is a must.

pendruid.com, 3863 Sperryville Pike, Sperryville, VA 22740

Sip Some Whisky

Visit Copper Fox Distillery, which concocts whiskies, brandies, and ryes through a floor malting process using barley and fruitwood. Owner Rick Wasmund studied whisky-making in Scotland before starting his distillery in 2005.

copperfoxdistillery.com, 9 River Ln., Sperryville VA 22740

Where To Stay

Sleep And Eat In Luxury

Perhaps the most well-known place to stay in the area is The Inn at Little Washington, which is about a 10-minute drive away from Sperryville’s Main Street. With 23 guest rooms, a stocked wine cellar, and a Michelin three-star restaurant, a stay here is nothing short of legendary,

theinnatlittlewashington.com, 309 Middle St., Washington, VA 22747

Stay In The Country

If the price tag at The Inn at Little Washington 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. About five minutes from Sperryville, this inn has five guest rooms, plus a five-bedroom farmhouse available, and five-course dining at the onsite restaurant (see above).

bluerockva.com, 12567 Lee Hwy., Washington, VA 22747

Try Some Ale In The Hopkins Ordinary Cellar

For a charming bed-and-breakfast option right in town, try Hopkins Ordinary, but the spot is no ordinary B&B. The site has five rooms and two cottages for guests to stay in. It also has a small-batch craft brewery in the cellar, which uses malted barley from the local Copper Fox Distillery and is open Thursday through Sunday. The unusual setup pays homage to the B&B’s history—it first opened in 1820 as an inn with a basement tavern. Around 150 years later, the inn was converted into apartments in the 1970s and was converted back to a BBA (“Bed & Breakfast & Aleworks”) in the 2010s. 

hopkinsordinary.com, 47 Main St., Sperryville, VA 22740