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One-tank road trip: Winchester, Virginia

Courtesy of Winchester-Frederick County Convention & Visitors Bureau. Used by permission.
Debi and I are spending the weekend in historic Winchester, Virginia, a town that changed hands during the Civil War more than seventy times. This area is rife with Civil War history and old battlefields, although few have been well preserved. First, Second, and Third Winchester are poorly preserved, although there are some nice parts such as Fort Collier and the Star Fort. Better preserved are the nearby First and Second Kernstown battlefields, parts of which are quite pristine.
Winchester is about two-and-a-half hours south of York in the scenic Shenandoah Valley just off of I-81. It’s an easy drive, and there are many good hotels in the area for an overnight stay.

Old Town Winchester has a variety of attractions, and is clean and safe for walking.
Of particular interest (besides the Civil War history, which is everywhere) is Old Town Winchester. The main street (Loudoun Street) has been blocked off and turned into a well-shaded pedestrian mall. It is lined with quaint little botiques, some tempting restaurants, specialty shops, a couple of good museums, coffee shops, and other fun places to tour. Not far away is a very large and fun antiques mall.
Courtesy of Winchester-Frederick County Convention & Visitors Bureau.
The old Frederick County Courthouse was erected in 1840. During the Civil War, it often served as a field hospital, prisoner-of-war detention spot, and military post for both armies. It is now a quality museum depicting life in Winchester during the war. it is well worth the modest admission price.
“Abram’s Delight” just south of Winchester is a 1750’s-era stone mansion erected by an early settler and miller, Abraham Hollingsworth. His grist mill is also preserved, as well as an early wooden colonial house. Nearby duck ponds and walking trails offer a great place for an early morning stroll, which I thoroughly enjoyed earlier this morning.
We will spend the rest of today touring a couple of this area’s more popular tourist attractions – Skyline Caverns in nearby Front Royal (the town was the site of yet another ACW battle), and then Luray Caverns farther to the south. We did some shopping yesterday in Winchester’s Apple Blossom Mall, and enjoyed a great dinner, and mapped out tomorrow morning’s Civil War tours.
During the Gettysburg Campaign, the Second Battle of Winchester opened the door for the Confederates to march into Pennsylvania, as Dick Ewell’s corps smashed the Federal defenders, a division of the VIII Corps under Robert Milroy. The division that later occupied York (Jubal Early’s) fought here, and this morning before Debi rose, I toured what is left of the battlefield of Second Winchester, where the Louisiana Tigers assaulted and captured a Union fort (a subject I cover in detail in my latest manuscript). Little did Early’s men realize at the time that their summer would take them to York, Pennsylvania, and for some, to the banks of the Susquehanna River at Wrightsville.
If you have not been to Winchester before, make it a point to take a weekend and explore this area. There’s so much to see and do. Southern hospitality, coupled with good food, historic attractions, the great scenery of the nearby Shenandoah National Park, and diverse shopping makes this a welcome weekend.