WINTER VILLAGE HOURS

This will be an open-air market and will be free for everyone to attend!

Printed event maps are available at the Winchester-Frederick County Visitors Center and Old Town Winchester businesses. Maps will also be available at the event’s Information Tent.

Event Highlights

The weekend begins Friday, December 5th with two fun holiday events!

Santa’s Pub Crawl (Friday evening):
Our friends at The Ivy Chest have organized a charity Santa’s Pub Crawl on Friday evening, benefitting Froggy’s Closet.

Grab your Santa hat (or full costume!) and come out for a holly jolly night in Downtown Winchester for the annual Santa’s Pub Crawl! Wristbands are $10 with proceeds benefitting Froggy’s Closet, an amazing local organization supporting children in need right here in our community.
How it works:
 Check in at 15 E Boscawen St starting at 5 PM to grab your wristband.
 Visit participating bars (listed here) and enjoy $5-or-less holiday specials.
 Sip, stroll, snap a photo, and spread holiday cheer — all for a great cause!

ShenArts Gallery Holiday Market (Friday evening):
This holiday season, ShenArts is turning the gallery into a festive marketplace filled with art, creativity, and cheer! The ShenArts Holiday Market will celebrate small works with big impact—unique, one-of-a-kind pieces perfect for gifting or collecting.

Full Winter Village Event (Saturday & Sunday):
Then on Saturday, December 6th and Sunday, December 7th, bring out the whole family to enjoy the specialty vendors, a tented Santa’s Village area with Santa, crafts, and even an appearance by the Grinch!

Take a complimentary horse-drawn wagon ride (weather permitting) from Shenandoah Carriage Company on Saturday between 12pm-6pm to enjoy the beautiful Old Town lights and displays. Horse-drawn wagon rides will be complimentary and first-come first served and handled by the carriage company staff.

There will be live caroling and music, demonstrative vendors, and you can grab a warm serving of gluhwein, a traditional hot mulled spiced red wine, from a participating restaurant and carry it with you as you shop. Several restaurants and shops will also be offering kinderpunch, a warm spiced non-alcoholic cider, and hot cocoa!

If you know of someone who needs a special message of hope, good wish or prayer, stop by our Wishing Tree area at the Taylor Pavilion and write out a wish for them and place it on the tree.

Live music schedule

Saturday:
11am-1pm – Wassailing by the Quire-Book Carolers 11am-1pm
12:30-2:30pm – City of Winchester Pipes & Drums 12:30-2:30pm
2:45-4:00pm – Rachel’s Merrie Melodies
Sunday:
11-11:30am – Low Brass Christmas (Shenandoah University)
11:30am-1pm – Alex Kilkus Trio
2-2:30pm – SCAA Youth Choir Caroling