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Nestled at the entrance to Shenandoah National Park, the Rappahanock County village of Sperryville, Virginia, is certainly tiny – only 571 acres, with two main streets and no traffic lights. But for all that it may lack in size and population – only 228! – it more than makes up for the charm of a small town.

First established in 1820, Sperryville was, at one point, the last stop before Thorton’s Gap on the long journey to new frontiers in the west. In fact, many pioneers stopped in town to buy Conestoga wagons from famous Sperryville wheelwright John Kriger. These days Sperryville is best known for its many restaurants, bars and friendly locals, including Leo, the corner store Black Lab. A “we are together” philosophy shared by residents old and new keeps growing with exciting small businesses, and visitors will have no problem spending a cool fall day among them. (Although spring, for Sperryfest, is another great time to visit.) Whether you want to go antiquing, savor a five-star meal, sip spirits in small quantities, or simply savor the beauty of Virginia’s Shenandoah Valley, this charming little town just 90 minutes away by car from Washington, DC, it’s easy to fill a wonderful weekend day. From the world famous Little Washington Inn to quaint lodges and guesthouses, there are plenty of plush and comfortable accommodations in and around town too, so feel free to extend this Saturday.

Ready to start planning your fall trip to the small town of Sperryville? Read on for the perfect itinerary, which is packed with our favorite restaurants, distilleries, antique rooms and more.

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Get up and grind

For a dose of caffeine, take a cardamom latte of Before after, and admire the view of the Thornton River from the Adirondack chairs in the back.


Shop till you drop

Bobette Swindler, the fourth generation owner of Spring gift shop in beech (Photo), offers everything from Fairtrade baskets and quilts to local jams and honey. Are you in the mood to choose? Antique Copper Fox houses 30,000 square feet of furniture and collectibles.


Go green

TO Wild Roots Apothecary, owner and herbalist Colleen O’Bryant offers tinctures, teas, cocktail syrups, and bath and body products that are popular throughout Northern Virginia.



Craig Batchelor’s three businesses in town, Sperryville corner store, Rappahannock Pizza Kitchen, and Francis bar, fall under the same roof. Look for the black Lab Leo, the corner store’s unofficial mascot, as you pack a picnic from the coolers of prepared food and gourmet cheeses, or wait for a pie – try the pork in the beehive! – the RPK wood-fired oven.


Taste the local products

Sperryville was once known as “Little Apple” because of its product packaging industry. The factories are long gone, but you can still buy bags of freshly picked Braeburns and Granny Smith at Thornton River Orchard and 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 Druid Brewing Pen. If spirits are more your thing, book a tour of Copper Fox Distillery. Don’t leave without a bottle of their fruitwood smoked whiskey.



Launched in 2015, the low-stakes, at three par School Nine The golf course, the first and only of its kind in Rappahannock County, winds past meadows of native wildflowers. Check-in takes place at the local pub.


Note a table

Michelin starred Inn in Little Washington first put Rappahannock County on the taste map, but Sperryville County Three blacksmiths (photo) is also generating buzz for its open-hearth kitchen and farm-to-table tasting menu.



At Mount Vernon Farm Inn, dormitories steeped in history range from a converted library to a private cabin.


Name your favorite little town!

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