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Winchester Things to Do – Attractions & Must See

Winchester: Things to Do

Winchester is a historic city in Northern Virginia. A trip to Winchester offers visitors plenty of things to do and see.

Old Town Winchester

While Winchester has grown to more than 25,000 people, the Old Town area is still a quaint historic area. Numerous businesses can be found on its small, old-fashioned pedestrian mall. There are many local restaurants, bars, shops and other stores that are generally not national chains.


The Winchester-Frederick Co. Visitors Center offers a combination ticket for three places to visit:

  • Abram’s Delight Museum – Built in 1754, this is the oldest home in Winchester. Beautifully restored and furnished with period pieces.
  • George Washington’s Office Museum – This log and stone building was used by Colonel Washington when he was Colonel of the Virginia Regiment during 1755-1756 when he was protecting the 300-mile frontier to the west.
  • Stonewall Jackson’s Headquarters – General Jackson prepared for his Romney campaign to the west, as well as The Valley Campaign here. There are civil war relics and memorabilia on display throughout the house.

All three of these places have docent-led tours. You can use the ticket any day during a week.

Museum of the Shenandoah

The Museum of the Shenandoah and Glen Burnie are located on the same campus. The museum is open year-round. This complex offers a tour of an 18th Century historic house, six acres of beautiful gardens and a museum that holds spectacular collections. This is a first class venue and highly recommended!

Civil War History

The Shenandoah Valley was a crucial battleground early in the American Civil War and Winchester, at the most accessible point of the valley, was the scene of numerous major battles and small skirmishes from 1861 to 1864. Various historical signs mark these events throughout town. Other noteworthy places Civil War buffs will want to see include the U. S. National Cemetery, Winchester National Cemetery, Mt. Hebron Cemetery and the Old Courthouse (now a Civil War museum, but during the war was used as a field hospital).

Other places of interest include the local farms (seasonal picking of pumpkins and apples), the First Presbyterian Church of Winchester (1788), Christ Episcopal Church (1745), the home where Patsy Cline lived as a teenager and young adult, and the burial site of Thomas, Lord Fairfax.

If you want something off-the-beaten track, the historic Harper’s Ferry is not too far away and Shenandoah National Park and its beautiful Skyline Drive is about 30 minutes south.

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Editor’s Note: The information contained on this page was compiled using real traveler reviews about things to do in Winchester, Virginia.

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