Nov 25, 2025
As the holiday season approaches, Winchester’s Old Town is preparing to transform into a magical winter wonderland. In this episode of The Valley Today, host Janet Michael and guest Justin Kerns, from Winchester-Frederick County Convention & Visitors Bureau, offer listeners an exclusive preview of the much-anticipated Winchester Winter Village. Their lively conversation reveals how this beloved event continues to evolve, bringing new experiences while preserving cherished traditions.
Expanding the Village: More Vendors, More Variety
This year, the Winter Village boasts a record number of vendors—nearly 47, up from 28 last year. According to Justin, the event team has carefully curated the vendor list to ensure a diverse selection of handmade goods, local crafts, and unique gifts, all while avoiding direct competition with Old Town’s brick-and-mortar businesses. The expanded layout, inspired by European Christmas markets, promises a cozy, meandering experience for visitors, with vendor tents thoughtfully arranged to encourage exploration and discovery.
Kicking Off with the Santa Crawl
The festivities begin on Friday night with the ever-popular Santa Pub Crawl, an adults-only event benefiting Froggy’s Closet, a local charity. Participants don festive attire, visit participating restaurants for drink specials, and enjoy the vibrant downtown atmosphere. Justin emphasizes the importance of keeping Friday night’s activities separate from the family-focused events on Saturday and Sunday, ensuring everyone can enjoy the Winter Village in their own way.
Family Fun in the Kinder Village
Transitioning to the weekend, families will find plenty to delight children in the Kinder Village. This dedicated area features crafts, character visits from Santa and the Grinch, and a safe, warm space for kids to create holiday memories. The organizers have improved the flow of the Kinder Village tent to reduce congestion and added stroller parking for convenience.
Special Touches: Wishing Trees, Carriage Rides, and More
No visit to the Winter Village would be complete without experiencing its signature touches. The wishing trees, now doubled to six, invite visitors to write down their hopes and dreams, creating a moving display of community spirit. Free horse and wagon rides, courtesy of the Shenandoah Carriage Company, offer a nostalgic journey through the twinkling lights of Old Town. Meanwhile, the aroma of roasted chestnuts and the allure of hot spiced wine and cocoa add to the festive ambiance.
Live Music and Local Partnerships
Throughout the weekend, live music fills the air, with performances by local groups and the city’s renowned pipes and drums. The event’s success, Justin notes, is due in large part to strong partnerships with organizations like Friends of Old Town and the dedication of local volunteers. These collaborations ensure the Winter Village remains a true community celebration.
A Gift to the Community
Perhaps most remarkable is the event’s commitment to accessibility. Admission is free, and nearly all activities—except the Santa Pub Crawl—are open to everyone. The organizers’ vision is clear: to draw people downtown, support local businesses, and foster a sense of togetherness during the holiday season.
Looking Ahead
As Janet and Justin wrap up their conversation, their excitement for the Winter Village is palpable. With new features, returning favorites, and a steadfast focus on community, Winchester’s Winter Village promises to be the most magical yet. Whether you’re a longtime attendee or planning your first visit, this event is sure to warm your heart and kindle your holiday spirit.
For more information, maps, and a full schedule of events, visit winchesterwintervillage.com.