Winchester, VA — the epicenter of the Civil War in Virginia

Just 90 minutes northwest of Washington, DC and about three hours southeast of Pittsburgh, there is a lovely little town called Winchester, Virginia — no relation to the rifle of the same name. From architectural attractions to foodie finds, Winchester is a ‘must-stop’ when you are in the area; and, it’s a delightful destination even if you aren’t in the area.

Winchester is tucked away in the northern end of the Shenandoah Valley. You’re just minutes away from the Allegheny Mountains to the west and the Blue Ridge Mountains to the east. With a drive in any direction, you’re bound to see hills on the horizon.


The site of many battles during the Civil War, Winchester occupied a most strategic location. Winchester changed hands between the Union and Confederate armies as many as 72 times during the Civil War — and as many as 13 times during just one day. At alternate times, General Sheridan of the Union Army and Stonewall Jackson of the Confederate Army occupied offices just one block apart.

Two other famous Civil War sites are just minutes away and are worth a visit:

Battle of Cedar Creek/Belle Grove

And the battles for Kernstown


Things are considerably more peaceful in Winchester now, and much more of a getaway destination. While we stayed there, we enjoyed the beauty and hospitality of the historic George Washington Inn. George spent years here in his younger life, surveying much of the area.

Another storied hotel nearby is the Wayside Inn, the oldest and longest running inn in the United States — in business since 1797. They offer 22 unique rooms and suites furnished with period antiques and artwork. Seven historic dining areas and Larrick’s Tavern can handle any appetite or thirst.

The Shenandoah Valley Discovery Museum would be ideal for younger children with floors and floors of hands-on exhibits. We enjoyed an evening of drinks and jazz on their rooftop while we were there.

Right next door, there’s a great burger and craft brew spot called 50/50 Taphouse — with 50 beers and 50 burgers to choose from. Super tasty and fun establishment.

Suitable for all, and with many eateries to keep you fueled, don’t miss Old Town Winchester — a pedestrian mall about a half-mile long with lots to see and do, including the Civil War Museum. Also of note, are the Red Fox Creamery for ice cream, the Winchester Book Gallery for books and great gifts, and Brewbakers Restaurant, which has been preparing delicious meals here for 103 years.

For more information and getaway ideas, be sure to check out

Disclosure: We were hosted by Winchester-Frederick County Convention & Visitors Bureau to be able to write this review. All opinions however, are always our own.

Originally published at Doug Bardwell.




Writer & photographer in print & online. Proud husband, father & grandfather. Engaged volunteer with Red Cross, human trafficking prevention & social concerns.

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Doug Bardwell

Doug Bardwell

Writer & photographer in print & online. Proud husband, father & grandfather. Engaged volunteer with Red Cross, human trafficking prevention & social concerns.

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