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Why Sperryville, Virginia, is the Best Small Town for Fall Leaf Peepin'

Country Living Logo By Sarah Zlotnick of Country Living | Slide 1 of 13: 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.

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.

© Michael Ventura / Alamy

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