🏡💚 Corcoran Connect's Guide to December Events in Winter Garden: Holiday Lights and Historic Charm
December in Winter Garden is pure magic! From the annual lighting ceremony to classic theater and Santa's neighborhood visits, the city's historic downtown is the place to be. At Corcoran Connect, we are proud to serve a community with such deep-rooted traditions. As Your Real Estate Concierge, we've compiled this list to ensure you don't miss any of the holiday cheer this month! 🏡💚
The Grand Holiday Kickoff: December 5th & 6th
Light Up Winter Garden December 5, 2025 | 6:00 PM – 9:00 PM Historic Downtown Winter Garden, 300 W. Plant Street
Welcome the season with the official lighting of the tree and more in historic downtown! 🎄 This free annual event kicks off the "Tis the Season" celebration with live entertainment, children’s activities, vendors, and more.
Winter Garden Farmers Market December 6, 2025 | 8:00 AM – 1:00 PM Downtown Interactive Fountain & Pavilion, 104 S. Lakeview Avenue
Start your Saturday morning at the award-winning Farmers Market! 🥕🛍️ You'll find over 100 vendors selling everything from fresh produce to holiday-ready artisan crafts and unique gifts.
Winter Garden Christmas December December 6, 2025 | 10:00 AM – 11:15 AM The route starts at S. Dillard Street, through Downtown
A cherished annual tradition! 🎅 Gather spectators for this long-standing parade featuring festive floats, marching bands, and, of course, the big guy himself at the end. Admission is free.
Holiday Night Market December 6, 2025 | 4:00 PM – 8:00 PM Downtown Interactive Fountain & Pavilion
The downtown area transforms into a festive open-air market under the stars! 🌙 Shop holiday goods from vendor booths, enjoy live holiday entertainment, visit with Santa, and take a trolley ride. Admission is free.
Winter Garden Christmas Golf Cart Parade December 6, 2025 | 6:00 PM Historic Downtown, West Plant Street
Don't miss the 13th Annual Christmas Golf Cart Parade! 🚗 An amazing sight of elaborately decorated golf carts spreads holiday cheer through downtown. After the parade, you can get a closer look at the holiday masterpieces parked throughout the area.
Ongoing Festivities and Community Connections
A Merry Winter Garden Light Show Select Dates in December | 6:00 PM – 9:00 PM Historic Downtown Winter Garden
A favorite holiday tradition is back! 💡 Enjoy a spectacular animated holiday-themed light show synchronized to music, projected onto the front façade of Winter Garden City Hall. Free to attend on select Fridays, Saturdays, and Sundays throughout the month.
Winter Garden Fire Rescue Annual Santa Run Nights: December 8, 9, 10, 11, 13 | 6:45 PM – 9:00 PM Northeast Winter Garden Neighborhoods
Look for the moving parade as Santa and his sleigh, along with elves of firefighters, police, and city staff, spread holiday music, treats, and good cheer through Winter Garden neighborhoods! Free to attend.
Holiday Fridays on the Plaza December 12, 2025 | 7:00 PM – 9:00 PM Historic Downtown, Centennial Plaza Gazebo
Enjoy live holiday music at Fridays on the Plaza, featuring the festive sounds of the Dickens Carolers! Free for all to enjoy.
Cocoa & Cookies with Santa Preschool Holiday Program December 19, 2025 | 10:00 AM – 12:00 PM Jessie Brock Community Center, 310 N. Dillard St.
Bring your little ones (ages 3 to 5) for a free holiday program! 🎅 Children will enjoy hot cocoa, holiday-themed crafts, and a meet and greet with Santa Claus.
Holiday Classics at the Garden Theatre
Holiday Flix at the Garden: White Christmas (NR) December December 7, 2025 | 2:00 PM – 4:00 PM Garden Theatre on Plant, 160 W. Plant Street
Catch this fan-favorite holiday classic movie for only $5 a ticket at the historic Garden Theatre. Presented by the City of Winter Garden. Reserve your tickets online now!
A Christmas Carol at the Garden Theatre on Plant December 22, 2025 | 8:00 PM – 9:30 PM Garden Theatre on Plant, 160 W. Plant Street
Experience the magic of Charles Dickens’ powerful tale of redemption. This spectacular touring production features timeless Christmas carols, haunting special effects, and an enormous dose of laughter. A wonderful holiday event for all! (Ticket purchase required).
Winter Garden's charm and spirit shine brightest in December! If you are considering making this wonderful area your home, the Corcoran Connect team is here to guide you with personalized expertise. Corcoran Connect: Your Real Estate Concierge. 🔑💚