Winchester’s Winter Wonderland

Visit Winchester for a true hometown holiday

Winchester offers a very traditional take for the holidays, especially on its downtown walking mall where lampposts are wrapped in garlands, the aroma of roasting chestnuts fill the air, horse-drawn carriages clip clop through the streets, and carolers tickle the ear with holiday favorites.

Historic Old Town Winchester

Stroll along the Loudoun Street Pedestrian Mall to explore more than 35 places to eat and 60 retail shops that combine urban amenities with small town charm. Find a unique gift or select something special for yourself, or try one of the new restaurants opening this year: Benny’s (giant pizza slices), Christina’s Cafe (sexi Mexi) or Macado’s (casual dining). The Broken Window Brewery is also new.

Experience life during the Civil War or admire centuries of history and architecture on a guided or self-guided tour. Highlights include the Old Courthouse Civil War Museum, George Washington’s Office Museum (see a lock of his hair), Stonewall Jackson’s Headquarters Museum and the Shenandoah Valley Discovery Museum (perfect for all ages.)

For arts and entertainment, take in a show at the Winchester Little Theater or a movie through the Magic Lantern Theater. The hotel and many restaurants also offer live music on weekends.

Patsy Cline: a Local Legend

In addition to its apple heritage and Apple Blossom Festival, Winchester may be best known for its hometown star, country singer Patsy Cline. The local legend tour includes her childhood home at 608 S. Kent Street. Restored and open for tours, it is bedecked for the holidays as it would have been during the time Patsy lived here, with decorations belonging to Hilda, Patsy’s mother, hanging on the tree. You can also tour sites important to Cline including the Gaunt’s Drugstore where she worked as a teen, Handley High School, WINC-92.5 FM Studio where she made her first radio appearance, and Shenandoah Memorial Park where pennies dot her grave marker.

New Year’s Eve

The downtown mall is the site for the annual First Night Winchester celebration, just surpassing its 35th year. Enjoy activities designed for the entire family at this alcohol-free event including animal shows, magicians, bands, ballroom dancing, and a huge fireworks display that rings in the New Year. Events are scheduled in buildings all along the mall for a truly walkable evening, with businesses and restaurants open as well. Don’t miss the Winchester “Apple Drop” to count down the final seconds to midnight.

Where to Stay: The George Washington, a Wyndham Grand Hotel

The George Washington Hotel, built in 1924, is one of Winchester’s tallest buildings, and after an extensive $25 million renovation completed in 2008, one of its most elegant hotels. Its fine architectural elements were preserved, along with its historic Colonial Revival and Neoclassical character and ornamentation. 

For many years, the hotel served as the Apple Blossom Princesses’ headquarters, with the ballroom hosting the Queen’s Ball. It also hosted numerous music and sports stars and celebrities. Artifacts and memorabilia from its notable history can be found throughout the property. Note the historic murals in the promenade and the Half Note Lounge.

Guests enjoy 90 elegantly-appointed rooms and suites (suites with spa showers, towel warmers and gas fireplaces), dining at George’s Food & Spirits, and a relaxing spa with an indoor swimming pool modeled after Roman bathhouses. It is conveniently located adjacent to the historic Old Town area.

Less than an hour’s drive from Northern Virginia, Winchester offers a little bit of small-town wonder to the holiday season.


Winchester-Frederick County Convention and Visitors Bureau, 

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