Winchester Christmas Events & Things to Do 2025

Discover a festive holiday shopping experience at the Holiday Handmade Market. Browse unique, handcrafted gifts from over 90 local artisans across two vibrant locations in Ranson and Bolivar. Find the perfect presents and soak in the seasonal cheer.

Experience the magic of the holiday season in Purcellville with a series of festive events. Witness the enchanting Town Tree Lighting, enjoy the vibrant Holiday Parade, and discover unique treasures at the Holiday Market. Families can create ornaments and meet Santa, while a special Holiday Lights Tour Map guides you...

Experience the magic of the holiday season in Purcellville with a series of festive events. Highlights include a charming Holiday Market at the Bush Tabernacle, a lively parade, and a special ornament workshop. Families can also capture cherished memories with Santa Claus and explore a map of beautifully decorated homes.

Experience the magic of Christmas in Middleburg, Virginia, on December 6, 2025. This cherished annual event transforms the town into a winter wonderland with a festive parade, tree lighting ceremony, and a heartwarming pageant. Enjoy a special breakfast with Santa, witness the thrilling Middleburg Hunt & Hounds Review, and explore...

Step back in time for a "Dickens of a Christmas" celebration in Middleburg, where the town transforms into a scene from a Charles Dickens novel. Enjoy caroling, dancing, and theatrical performances. Don't miss the traditional Christmas Parade and the Middleburg Hunt Review, plus enchanting horse-drawn carriage rides.

Step into a winter wonderland at Lights on the Lake, a dazzling holiday light show in Harpers Ferry, WV. This enchanting walkthrough event features over 500,000 twinkling lights and themed displays along the shores of Lake Shannondale. It's the perfect festive tradition for creating family memories and capturing holiday photos.

Step back in time with the Hillsboro Holiday Homes Tour, a captivating journey through six historic residences adorned with festive greenery. Experience the warmth of the season with the scent of pine and crackling fires as you explore 18th and 19th-century homes. Enjoy live music and historical narratives during guided...

Lace up for the 15th Annual South Berkeley Christmas 5K, a festive run that kicks off the South Berkeley Christmas Parade. This mostly flat 5K course winds along the parade route, ensuring plenty of cheering spectators. Festive costumes are highly encouraged, adding to the holiday spirit. All proceeds benefit The...

Immerse yourself in the holiday spirit in historic Shepherdstown, with festivities commencing right after Thanksgiving and continuing through December. The celebration ignites with a bonfire, Mrs. Claus's enchanting storytelling, and a magical tree lighting ceremony. Stroll down German Street, where shops and restaurants gleam with festive decorations, inviting you to...