Downtown Holiday Events

Holiday House TourThe holidays are fast approaching, so make sure you mark your calendars for all the great events planned in Old Town Winchester for the next couple months. More details for each event will be posted in the near future.

  • Plaid Friday – November 28 at Downtown Businesses: 

Plaid Friday is the fun alternative to “Black Friday” designed to promote both local and independently- owned businesses during the holidays. Shoppers are encouraged to wear plaid!

  • City of Winchester Parade & Tree Lighting Ceremony -Monday, December 1:

The parade begins a 7 p.m. on Piccadilly St. at Cameron St. Watch along Piccadilly St., Braddock St., and Cork St. Join us after the parade for the downtown tree lighting on the walking mall near the Old Court House Civil War Museum.

  • Santa’s Headquarters – December 5-6:

Friday, December 5 (5-7 p.m.) and Saturday, December 6 (11 a.m.-1 p.m.) at the Godfrey Miller House. 28 S. Loudoun Street. Come take pictures with Santa and make a holiday craft to take home.

  • Annual Candlelight Tour & Open House – December 5-6:

Friday, December 5 (6-8 p.m.) and Saturday, December 6 (3-7 p.m.). Presented by the Winchester-Frederick County Historical Society. Tour and Open House include Abram’s Delight, Stonewall Jackson’s Headquarters Museum, and George Washington’s Office Museum. Free admission.

  • Preservation of Historic Winchester’s Annual Holiday House Tour – Saturday, December 6 and Sunday, December 7:

This year, the tour will feature homes in the Potato Hill (South Loudoun Street) neighborhood. Visit the Bough and Dough Shop at 315 W. Boscawen Street to purchase holiday greenery, baked goods, and gifts. For more information, visit

  • Holly Jolly Celebration – Saturday, December 13. Noon-5 p.m.:

Caroling and holiday activities including free wagon rides from 1-3 p.m. Specials at shops and restaurants all day.

  • First Night Winchester – Wednesday, December 31:

Celebrate New Year’s Eve in Old Town! Information is available at

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