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Small Charming Towns of the Valley. Home » Suggested Itineraries » Small Charming Towns of the Valley. Set up your base camp in Winchester-Frederick County or White Post-Clarke County, VA. From hotels to B&Bs, RV and tent camping, there are numerous lodging options.
Find the top 15 cities, towns, and suburbs near Winchester, VA, like Front Royal and Martinsburg, and explore the surrounding area for a day trip.
These four highways follow city streets through downtown Winchester, with U.S. Route 17 coming to its northern terminus. Virginia State Route 7 also serves Winchester, terminating in downtown. Virginia State Route 37 bypasses the city to the west.
If you love vibrant small towns and rural scenic beauty, visit Winchester-Frederick County in Virginia’s Shenandoah Valley! Feel the heartbeat of this thriving community in Old Town Winchester, where you can stroll a two-block pedestrian mall bursting with unique shops and outdoor cafes.
- Go to a farm market. This season is their bread and butter, and for good reason. You’ve got the big, ever-popular ones like Marker-Miller, Virginia Farm Market, and West Oaks Farm Market and then some really unique and fun smaller finds like Hill High Farm, the Homestead Farm at Fruit Hill Orchard, Richard’s Fruit Market, Rinker Orchard s, and Shen Val Farm Market!
- Turn off that GPS and go for a country drive. Yes, I’m telling you to get lost (but seriously, in a friendly way) out on our local roads. We’ve got fields, orchards, rolling hills and mountains all within about 20 minutes of Old Town Winchester.
- Roll up your sleeves and pick an apple. Surprise, this is apple country. I know you probably already knew that, but to really grasp the scale of it you’ve got to actually get into the trees at one of those orchards.
- Hike or mountain bike to a vista point, even if just for an hour or two. The Tuscarora Trail is truly a hidden gem, but may not remain so once people realize there’s alternative for Old Rag to get beautiful valley vistas.
The Winchester, VA metro area, situated in northern Virginia close to the West Virginia border, holds a unique spot in American history. Established in 1752, Winchester has seen significant events, especially during the American Civil War where it was a key strategic location.
Get directions, maps, and traffic for Winchester, VA. Check flight prices and hotel availability for your visit.
