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5 Reasons to Visit Winchester, VA


Small towns make great getaways, especially in fall when rows of trees with red and yellow leaves line the sidewalks and the surrounding hillsides billow with color. Winchester, in Virginia's Shenandoah Valley, adds interesting museums, Civil War history, a comfortable hotel and more.

Old Town Winchester

Small towns make great getaways, especially in fall when rows of trees with red and yellow leaves line the sidewalks and the surrounding hillsides billow with color. Winchester, in Virginia’s Shenandoah Valley, adds interesting museums, a restaurant that worth’s the drive even from Washington, DC, 75 miles away, acres of pick-your-own apple orchards, Civil War history, and a comfortable hotel.

Five Finds in Winchester, VA.

1. Museum of the Shenandoah Valley. The museum surprises with its interesting galleries showcasing: Shenandoah Valley furnishings from rough-hewn benches for log cabins to tall case clocks that graced fine homes; miniature houses with expertly crafted details whose décor includes crystal chandeliers and “Gone with the Wind” drapes; as well as 18th century portraits of English gentry.

“CUT! Costumes and the Cinema,” which debuted October 3, displays 43 movie costumes depicting the 1500s to the 1900s. The attire conveys a sense of each era. The brown leather jacket and velvet breeches worn by Colin Farrel as Captain John Smith in “The New World”, circa 1607, are plain compared with Johnny Depp’s 1700s era pirate-style look as swashbuckling Captain Jack Sparrow in “Pirates of the Caribbean: The Curse of the Black Pearl.” Compare that with the elaborate ball gowns adorned with ribbons and flowers worn by Keira Knightley in “The Duchess of Devonshire.” CUT! is on view through Feb. 28, 2016. 888-556-5799.

eM Restaurant

Essential to any successful getaway is a really good restaurant. Chef Will Mason, who grew up in Winchester, serves imaginative but unfussy New American cuisine. The seared scallops with couscous were cooked perfectly as was the pork chop with pineapple hoisin BBQ sauce paired with a side of cheddar macaroni and cheese. The carrot and pumpkin cake came deconstructed with rosettes of cream cheese icing on the plate. It was a lovely end to a good meal. The chef chose the “e” and “m” for the restaurant’s name because those are his mother’s and grandmother’s initials. 540-431-5139.

2. eM Restaurant.

3. Marker-Miller Orchards. More than 20 varieties of apples—including Red Delicious, Golden Delicious, Nittany, Stayman, Grannysmith, and Fuji—grow on the farm’s 325 acres. Pick your own from the trees or select from the crates. The farm market also sells apple butter, jams, jellies, apple cider donuts, pies, and cookies. Kids can romp on the playground equipment in sight of the picnic tables. 540-662-1391.

4. Old Court House Civil War Museum. It’s easy to imagine the proceedings in the 1840s courthouse, but much harder to picture 1,500 prisoners held on the small lawn outside as they were during the Civil War, a period when Winchester changed hands more than 70 times. Then the building served as a hospital and barracks for whichever side held power and a prison for those captured. The facility displays cases of Civil War items such as letters, hog hair toothbrushes, belt buckles, artillery, and more.

Old Town Winchester

The most interesting item to us is the still visible curse aimed at Jefferson Davis carved into the wall. The vitriolic Union Soldier wants Davis to be swallowed by a shark that’s swallowed by a whale that ends up in hell in the devil’s belly. But that’s not enough. The curse ends with “May he (Davis) be put in the north west corner with a south east wind blowing ashes in his eyes for all ETERNITY.” 540-542-1145.

In town, you can tour Stonewall Jackson’s headquarters and stroll the Stonewall Confederate Cemetery. Civil War battlefields surround Winchester.

5. The George Washington, a Wyndham Grand Hotel. Constructed in 1924, the hotel was named after the first president who had surveyed the region early in his career. In 2011 Wyndham spent $30 million restoring and renovating this property conveniently located in Winchester’s Old Town near the pedestrian mall. The staff is friendly, the lobby has free coffee and tea, and the rooms are comfortable. Like all good historic buildings, legend has it that this one is haunted. A lady sometimes appears looking for her lost lover and Confederate soldiers have been spotted in the lobby at night. 540-678-4700.

Top and bottom photos courtesy of the Winchester-Frederick County Convention and Visitors Bureau. Restaurant photo courtesy of eM Restaurant.

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