Holly Jolly Celebration


The Holly Jolly Celebration will return to Old Town Winchester for 2017 on December 9th! More details are coming soon, but check out last year’s details below for more info.


Come spend some time in Old Town this holiday season during our Holly Jolly Celebration on December 10th! Enjoy caroling and holiday activities 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 anytime 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, relax and watch nostalgic animated holiday programs, listen to a story in the reading corner, and enjoy a special treat!

Click here for a Printable PDF of Events



Full Schedule of Events:

10:00 – 2:00

Santa’s Headquarters at the Godfrey Miller Center –Take a photo with Santa and make a craft to take home. Godfrey Miller Home, 28 S. Loudoun St. (Free)

10:00 – 2:00

Stuff-a-Truck for Local Families in Need – (Rouss Avenue near Old Court House Civil War Museum) Winchester Fire & Rescue and Winchester Social Services. Collecting winter gear, toys, gifts for teens, and non-perishable foods. Items will be donated to Winchester Public Schools, C-CAP, Highland Food Pantry, Salvation Army and the Timbrook House.

10:00 – 4:00

Elf on a Shelf Scavenger Hunt – 
Themed scavenger hunt. Collect treats along the way. Winner will receive a special gift. Winner will be announced at 5:00 p.m. Must be present to win. Purchase map at 9 N. Loudoun St. ($5 per person)

10:00 -11:00

Caroling by Our Savior Lutheran Church

11:00 – 12:00

Caroling by Girl Scout Troop 40641

11:00 – 3:00

Christmas Tree Sale and Hot Chocolate  – Boy Scout Troop 2 set up in front of the First Presbyterian Church, 
116 S. Loudoun St.

12:00 -1:00

Caroling by Heritage Baptist Church

1:00 – 3:00

Horse Drawn Wagon Rides  – Meet at Old Court House Civil War Museum Lawn, 20 N. Loudoun St.
 Time tickets available, space is limited. (Free)

1:00- 3:00

Posh Pets Photos with Santa  – Posh Pets Boutique, 16 S. Loudoun St. Benefiting Dakota’s Dream Animal Rescue ($10)

1:00 – 4:00

Event for All Ages at Handley Regional Library  – Offering Make-and-Take Holiday Crafts, Nostalgic Animated Holiday Movies, Lively Holiday Music, and North Pole Ring Toss Game. 
100 W. Piccadilly St. (Free)

1:00 – 4:00

Wine Tasting featuring Gluhwein, Beaujolais Nouveau and More
 – Murphy Beverage Company, 167 N. Loudoun St.

2:00 – 3:00

Caroling by Calvary Church of the Brethren


Visit with the Grinch
 – Kid’s Hot Chocolate or Kid’s Milk and Cookies for $1.50. The Hideaway Café, 200 N. Braddock Street

3:00 – 4:00

Caroling by Arts Chorale of Winchester

3:00 – 4:00

Ghosts of Christmas Past: A Civil War Christmas – 
Educational Festive Family Event, Hot Chocolate, Treats, Make-and-Take Photo Frame Craft. 
Ghost Tours of Old Town Winchester, VA, 9 N. Loudoun St. ($10 per family)

All Day

Discovery Museum Holiday Art Project in Leo’s Corner  – Free with paid museum admission.
 Shenandoah Valley Discovery Museum, 19 W. Cork St.

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 yrs.

Post Holly Jolly

6:00 – 9:00

Krampus, Cookies, and Cocktails Meet Krampus, enjoy refreshments and shop! Tin Top Art & Handmade, 130 N. Loudoun St.

Retail Specials During Holly Jolly Event

The Black Rose, 11 S. Loudoun St. 10% off entire store

Bright Box Theater, 15 N. Loudoun St. 10% off Bright Box Gift Certificates

Knit 1 Purl 2, 20 W. Boscawen St. 20% off yarn and flags

Flavor Pourfection, 27 N. Loudoun St. 10% off any gift basket or gift set

Handworks Gallery, 150 N. Loudoun St. Cookies and Treats

Lox Salon, 209 E. Boscawen St. 20% off all color services, $35 shampoo, cut, and blow-dry/style

Michelle’s Wigs and More, 33 W. Piccadilly St. 15% off storewide

Northern Virginia Tours, 9 N. Loudoun St. $2 Stocking Stuffers

Old Town General Store, 106 S. Loudoun St. BOGO Hot Chocolate

Once Upon A Find, 48 S. Loudoun St. Free donut and hot beverage with any purchase and receive a $5.00 Santa Buck for every $25.00 purchase.

Shenandoah Valley Discovery Museum Store, 19 W. Cork St. 5% off store purchases

Thinker Toys, 202 S. Braddock St. $5 Come Back Cash for every $50 spent

White House Country Store, 204 S. Loudoun St. Warmers, wax melts and Snoozies on sale




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