Holiday Open House

Here comes Santa Claus, here comes Santa Claus, right down…to Old Town Winchester!

Follow Santa down from a morning of holiday fun at the War Memorial Building directly to Old Town, where you can take in the festive storefronts and enjoy holiday deals, meet Santa & Mrs. Claus as they stroll the Walking Mall, or listen to live holiday music! Do your holiday shopping and then bring your purchases over to our free gift wrap station at the Taylor Pavilion! Explore the fun crafts and Christmas events going on in our many wonderful businesses and restaurants! Or just grab a hot cocoa and take a walk over the the historic Handley Library to enjoy the Gingerbread Jamboree and take your library card for a spin. There’s so much for the whole family to enjoy!

WEATHER UPDATE: Some performances and activities have been pre-emptively cancelled due to weather concerns. Follow us on social media or keep checking back for announcements!


  • 8:30am & 11:30am, Breakfast with Santa (George Washington Hotel) – Includes buffet breakfast bar, family photo with Santa, Christmas caroling, close-up magic and balloon art, hand and face painting. Contact for reservations.
  • 11:30am, Santa arrives to Old Town
  • 11:30am-1pm, Billy Thompson Group (Taylor Pavilion)
  • 12-2pm, Santa & Mrs. Claus walk the mall
  • 12-5pm, free gift wrapping (Taylor Pavilion)
  • CANCELLED 1pm, Winchester Little Theater carolers (Taylor Pavilion)
  • CANCELLED 2pm, Sing! Shenandoah carolers (Taylor Pavilion) – Sing! Shenandoah – Female Acapella Group – Rehearse Mon nights at 6:30 at Opequon Presbyterian Church 217 Opequon Church Lane in Winchester.  Contact:  Con Burch 540-335-6111
  • 2-4pm, Gingerbread Jamboree (Handley Library)
  • 3pm, Holiday Concert (MSV)
  • CANCELLED 3-5pm, Valley Chorale of Front Royal Concert (Handley Library)
  • 5-10pm, Old Town Spirit in effect! – During this time, enjoy adult beverages from our local businesses while you browse the shops and admire Old Town’s holiday decor. Look for the “Yes” signs on the doors of participating businesses!
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