Come spend some time in Old Town this holiday season. During our Holly Jolly Celebration, enjoy caroling and holiday activites including free holiday wagon rides from 1-3 p.m. Specials at shops and restaurants all day.
Families are invited to drop by the Handley Regional Library any time between 1 p.m. and 4 p.m. to enjoy a festive atmosphere of holiday music and take part in a variety of activities. Create a make-and-take holiday craft, play the North Pole ring toss, relax and watch nostalgic animated holiday programs, listen to a story in the reading corner, and enjoy a special treat!
Want to go shopping in the great stores in Downtown Winchester, but don’t have a babysitter? Problem Solved! From 6 p.m. – 8 p.m., the Shenandoah Valley Discovery Museum will provide a fun and safe environment for your child(ren) while you pick up something special for someone special. Ages 5-up. Pre-registration up to December 12: $8.00; Registration on December 13: $10.00. Snacks will be available. *Additional charge for late pick up applies.
Click here for a Printable PDF of Events
Caroling by Our Savior Lutheran Church
Old Town Winchester History Tour – Meet at Kurtz Building, 2 N. Cameron St. $5 per person, payable to the guide. Reservations required: (540) 722-8700
Christmas Tree Sale and Hot Chocolate – Boy Scout Troop 2 set up in front of First Presbyterian Church, 116 S. Loudoun St.
Silly Christmas Hat Photos – Hosted by YDC (Youth Development Center) in front of Old Courthouse Civil War Museum, 20 N. Loudoun St. Children’s craft packets will be available.
Gift Wrapping – Hosted by Evans Home at Bright Box Theater, 15 N. Loudoun Street
Hot Cider – Hosted by Winchester Exchange Club in front of Virginia National Bank, 186 N. Loudoun St.
Children’s Holiday Crafts – Hosted by Boys and Girls Club of Northern Shenandoah at Godfrey Miller Home, 28 S. Loudoun St.
Winchester Architectural Tour – Led by Tim Youmans. Meet at the Old Town Welcome Center, 33 E. Boscawen St.
Caroling by Winchester Musica Viva
The Young Historical Scions of James Wood Historical Tours – Meet at Village Market & Bistro, 2 S. Loudoun St.
Winchester Art Market – In the Bright Center, 9 N Loudoun St.
Visit with Santa – Hosted by Shenandoah Valley Discovery Museum. 19 W. Cork St. Free to have your photo taken and share your list.
Free Horse Drawn Wagon Rides – Courtesy of Union First Market Bank. Meet at Old Courthouse Civil War Museum, 20 N. Loudoun St.
Old Town Winchester History Tour – Meet at Kurtz Building, 2 N. Cameron St. $5 per person, payable to the guide. Reservations required: (540) 722-8700.
Handley Regional Library Free Event for Youth & Families – Offering crafts, movies, games and stories, 100 W. Piccadilly St.
Christmas & Holiday Stories featuring local author Jay Foreman – Hosted by Winchester Book Gallery, 185 N. Loudoun St. Readings will begin every 30 minutes.
Caroling by Heritage Baptist Church
Caroling by Calvary Church of the Brethren
The Young Historical Scions of James Wood Historical Tour – Meet at Village Market & Bistro, 2 S. Loudoun St.
Caroling by Sacred Heart Academy
The Young Historical Scions of James Wood Historical Tour – Meet at Village Market & Bistro, 2 S. Loudoun St.
Caroling by The Arts Chorale of Winchester – At the Taylor Pavilion, 119 N. Loudoun St.
Caroling by Kenneth Ritter – In front of Old Town Post Office, 132 N. Loudoun St.
Caroling by Eagle Heights Presbyterian Church
Holly Jolly Parents Night Out – Hosted by Shenandoah Valley Discovery Museum, 19 W. Cork St.
$8.00 Members; $10.00 Non-Members: Limited to ages 5+
Advanced Registration Only: Call (540) 722-2020 to register.
Snacks available, Maximum: 50 kids.
Stocking Stuffer Drive – Posh Pets Boutique, 16 S. Loudoun St. Benefits Social Services of the City of Winchester & Frederick County. Collecting small toys, personal care items, snacks, candy, etc. for ages 2-17 years.
Half priced children’s meals until 4 p.m. – Union Jack Pub & Restaurant, 101 N. Loudoun St.
Dog Treat Samples – Dancing Dog Natural Market, 157 N. Loudoun St.