Winter Wonderland Special Events
November 28th: Opening Night!
Join us on Friday, November 28th as we kick off the holiday season with our Opening Night celebration! Enjoy the magic of our tree lighting ceremony and capture the fun with Snap n’ Share’s photo booth, perfect for creating and sharing festive memories with family and friends. Half of the proceeds from opening night ticket sales will benefit Chain of Checks, supporting those in need within our community. Come out and celebrate the start of the season with lights and holiday cheer!
Tuesday, December 2nd: Sherando Jazz Ensemble
Enjoy an evening of festive cheer as the Sherando Jazz Ensemble fills Winter Wonderland with the smooth sounds of the season! Join us for a night of holiday classics performed by these talented student musicians. Their lively performance is sure to add an extra sparkle to your Winter Wonderland experience! Performance begins at 6:30 pm at The Lodge.
Tuesday, December 9th: Snap 'n Share Photo Booth & The River 95.3
Snap ‘n Share Photo Booth will be on-site to capture your festive memories with family and friends, perfect for sharing holiday cheer. Plus, The River 95.3 will be broadcasting live, bringing the sights and sounds of Winter Wonderland straight to the community.
Sunday, December 14th: Santa's Holiday Makerspace
Make a cheerful holiday craft and send your wishes straight to Santa at our Letters to Santa station. A magical evening for kids of all ages!
Monday, December 15th: Winter Village
Each Frederick County Parks & Recreation basicRec site will build a winter-themed village from recycled materials! Visit the lodge on December 15th to vote—the winning site earns a pizza party.
Tuesday, December 16th: Snap n'Share Photo Booth
Snap ‘n Share Photo Booth will be on-site once again to capture your festive memories with family and friends!
Wednesday, December 17th: Admiral Byrd Jazz Band
Add some swing to your holiday season with a lively performance by the Admiral Byrd Middle School Jazz Band! These talented young musicians will bring the energy and spirit of the season to life with festive tunes and jazzy favorites. Don’t miss this fun, feel-good performance that’s sure to get your toes tapping and your heart smiling!
Thursday, December 18th: Windsong Community Chorus
This talented local choir will fill the night with beautiful harmonies and festive favorites that capture the magic of the season. Gather your family and friends, stroll through the lights, and enjoy an evening of music and cheer you won’t want to miss! Performance begins at 6:30 pm at The Lodge.
December 19th-23rd: Trolley Rides
Enjoy a magical ride on the Winchester Trolley to Winter Wonderland from December 19th to 23rd. Board the historic Winchester Trolley at the Frederick County Government parking lot (located behind 107 North Kent Street) and soak in the festive holiday lights and decorations as you travel to the dazzling Winter Wonderland at Clearbrook Park. Once you arrive at Clearbrook Park for the Walking in a Winter Wonderland it is a .5 mile illuminated walking path.
Before we depart, grab a bite to eat or a drink and take some family pictures with the decorations the George Washington Hotel has on display inside and outside! This hassle-free experience is perfect for creating cherished family memories amid the stunning light displays and winter fun. The Trolley will be parked behind the County Administration Building at 107 North Kent Street, Winchester, VA 22601.
Choose from two time slots: depart at 5pm, arriving by 5:30pm and returning by 7pm, or depart at 6pm, arriving by 6:30pm and returning by 8pm. Tickets include trolley ride and admission into Winter Wonderland. Trolley ride tickets are required for ages 3 and up; ages 2 and under free, no ticket required for entry.
Fridays & Saturdays (except Saturday, 12/6): Pony Rides!
Join us for a pony ride with Faithful Heart Horses & Friends: $10 cash or card paid directly to Faithful Heart Horses & Friends.
