Winter Wonderland Special Events

November 28th: Opening Night!

Join us on Thursday, 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 Dececember 15th  to vote—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 Choir

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! Board the historic Winchester Trolley at the Frederick County Government parking lot (located behind 107 N. Kent St) and soak in the festive holiday lights and decorations as you travel to the dazzling Winter Wonderland at Clearbrook Park. Once you return to the George Washington Hotel, grab a complimentary cup of hot cocoa and take some family pictures with the decorations! Choose from two time slots: depart at 5 pm, arriving by 5:30 pm and returning by 7 pm, or depart at 6 pm, arriving by 6:30 pm and returning by 8 pm. Tickets include trolley and admission into Winter Wonderland. Tickets 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.