Holly Jolly Celebration

The Old Town Winchester Holly Jolly Celebration returns on December 8th, 2018. More details are coming soon, but check out last year’s event for more info:


Come spend some time in Old Town this holiday season during our Holly Jolly Celebration on December 9th! Enjoy caroling and holiday activities including free holiday wagon rides from 1-3 p.m. Specials at shops and restaurants all day.

Children can create a holiday craft while waiting to meet Santa Claus at Santa’s Headquarters from 10 a.m. – 2 p.m. at the Godfrey Miller House (28 S. Loudoun Street). Thank you to City of Winchester Parks & Recreation for assisting with Santa’s Headquarters!

Free horse drawn wagon rides will be offered from 1-3 p.m. Meet in front of The Shenandoah Valley Civil War Museum (20 N. Loudoun Street) to pick up a time ticket beginning at 1pm. No need to stand in line! Enjoy holiday shopping and dining in Old Town and return to the wagon area prior to your ticket time.

Caroling groups including Heritage Baptist Church, Our Savior Lutheran Church, First Presbyterian Church, and Calvary Church of the Brethren will be strolling downtown spreading holiday cheer!

Click here to download the Holly Jolly Schedule


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