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The population of this city is 26,000.
This destination is situated 120 miles from the state capital, Richmond, and 7 miles from Brucetown.
If you love your wine, don't overlook the opportunity to treat your taste buds at the Bluemont Vineyard and the Chester Gap Cellars. The Glen Manor Vineyards and the Veramar Vineyard are two other popular stops where you can get a more intimate understanding of the region's wine industry.
Skyline Caverns and Jim Barnett Park are some of the best places to bask in the sun, go for a picnic or just watch life pass by. There's also a good deal of fun to be had at State Arboretum of Virginia and Cedar Creek and Belle Grove National Historical Park.
Want to know about upcoming events, tours, local hotspots or kid-friendly outings? Winchester Visitors Center and Dickey Ridge Visitor Center are excellent resources for any questions you have about your stay.
Put on some sensible shoes and pack some snacks. It's time for a day of adventure out in nature at Dickey Ridge Trail.
Wander the halls and admire the marvellous collections at the Museum of the Shenandoah Valley. You're bound to find something which sparks your curiosity.
Exhibiting a selection of exciting science innovations, Mackintosh Fruit Farm offers everything you need to keep your mind buzzing.
Grab a hot cup of coffee and spend the afternoon gallery hopping between the Duvall Designs Gallery and the Fire House Gallery. Boasting a wide array of carefully curated pieces, these popular exhibits offer something for everyone.
Do you want to explore a few history-filled attractions? An excursion to the Shenandoah University or Belle Grove Plantation offer a fascinating glimpse into Winchester's bygone times. Stonewall Jackson's Headquarters and George Washington's Office are also worth a visit.
Indulge in some soul-searching or just quietly absorb the stillness of Holy Cross Abbey, a historic spiritual space.
You might swing by Apple Blossom Mall wanting to grab some essential supplies, but you'll probably walk out with quite a good deal more than that.
Check what's on at the Winchester Little Theater, because there's nothing quite like seeing a spectacular show. Wayside Theater is another top venue if you're up for more.
Don't mind a little healthy competition? Then slip on your best golf glove and challenge some friends to a round at Virginia National Golf Club.
They mightn't be the first things you put on your must-see list, but the Handley Regional Library and the Barns of Rose Hill are still well worth an outing. Don't forget to stop by Rocking S Ranch and Watermelon Park Campground either.