16 Ways to Spend the Perfect Fall Day in Sperryville, Virginia
Nestled at the entrance of Shenandoah National Park, this tiny Rappahannock County village offers prime leaf-peepin’ alongside a bounty of eateries, drinkeries, and friendly locals.
Nestled at the entrance of Shenandoah National Park, the Rappahanock County village of Sperryville, Virginia, is certainly tiny—just 571 acres, with two main streets and zero stoplights. But for all it may lack in size and population—just 228!—it more than makes up for with small town charm.
First established in 1820, Sperryville was, at a certain point in time, the last stop before Thorton’s Gap on the long journey to new frontiers out west. In fact, many pioneers stopped in town to purchase Conestoga wagons from renowned Sperryville wheelwright John Kriger. These days, Sperryville is best known for its bounty of eateries, drinkeries, and friendly locals—including Leo, the corner store black Lab. A we’re-in-it-together ethos shared by residents old and new keeps it booming with exciting small businesses, and visitors will have no problem whiling away a crisp fall day in their midst. (Though the spring, for Sperryfest, is another fine time to visit.) Whether you wish to go antiquing, enjoy a five-star meal, sip small-batch spirits, or simply savor the beauty of Virginia’s Shenandoah Valley, this sweet small town—located just a 90-minute drive from Washington, DC—makes it easy to fill out a wonderful weekend day. From the world-famous Inn at Little Washington to quainter lodges and B&Bs, there are also plenty of plush and cozy accommodations in town and nearby, so feel to stretch that Saturday into an extended stay.
Ready to start planning your fall trip to the small town of Sperryville? Read on for the ideal itinerary, which is filled with our favorite restaurants, distilleries, antique halls, and so much more.
Rise and Grind
For a caffeine fix, grab a cardamom latte from Before & After, and take in the views of Thornton River from the Adirondack chairs out back.
Picture This
On the “must ’gram” list: the “Welcome to Sperryville” mural at Happy Camper Equipment Co., which shop owner Rob Chapman painted himself. While you’re there, be sure to pick up a souvenir pennant.
Shop 'til You Drop
Bobette Swindler, the fourth-generation owner of Beech Spring Gift Shop (pictured), stocks everything from fair-trade baskets and quilts to local jams and honeys. More in the pickin’ mood? Copper Fox Antiques is home to 30,000 square feet of furniture and collectibles.
Go for the Green
At Wild Roots Apothecary, owner and herbalist Colleen O'Bryant offers tinctures, teas, cocktail syrups, and bath and body products that are beloved throughout Northern Virginia.
Order Up
Craig Batchelor’s three in-town businesses, Sperryville Corner Store, Rappahannock Pizza Kitchen, and Francis bar, fall under the same roof. Look out for black Lab Leo, the unofficial corner shop mascot, as you assemble a picnic lunch from the coolers of prepared foods and gourmet cheeses, or wait for a pie—try the Hog in the Hive!—from RPK’s wood-fired oven.
Sample the Local Produce
Sperryville was once known as “Little Apple” because of its produce-packing industry. The factories are long gone, but you can still grab bags of freshly picked Braeburns and Granny Smiths at Thornton River Orchard & Market.
Wet Your Whistle
Brothers Lain, Van, and Jennings Carney (pictured) make craft beers and ciders using traditional methods and their own well water at Pen Druid Brewing. If spirits are more your thing, book a tour of Copper Fox Distillery. Don’t leave without a bottle of their fruitwood-smoked whiskey.
Play a Round
Debuted in 2015, the low-stakes, three-par Schoolhouse Nine golf course—first and only of its kind in Rappahannock County—winds its way along native wildflower meadows. Check-in is at the local pub.
Stretch Your Legs
Nearby Shenandoah National Park boasts the best foliage for miles around. Cruise the scenic Skyline Drive, or take in the sweeping views on foot with a 9.4-mile circuit hike to Old Rag Mountain.
Score a Table
The Michelin-starred Inn at Little Washington first put Rappahannock County on the gustatorial map, but Sperryville’s Three Blacksmiths (pictured) is also garnering buzz for its open-hearth cooking and farm-to-table tasting menu.
Hit the Hay
At the Inn at Mount Vernon Farm, the steeped-in-history sleeping quarters range from a converted library to a private cabin.
Nominate Your Favorite Small Town!
Where should we mosey to next? Tell us at countryliving@hearst.com, or start planning your next getaway with more of our small town guides:
• The 50 Best Small Towns for Antiques
• 20 Small Towns That Leave a Big Impression
• 18 Photos That Capture the Charm of Small Town Living
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