FreeA Merry Winter Garden Light Up & Holiday Stroll
Through Jan 3Dec 4 – Jan 3 · 6:00 PM – 9:00 PM · Opening Light Up Celebration Friday, Dec 4, 2026, 6:00 PM – 9:00 PM; holiday light canopy and interactive displays illuminated nightly through Jan 3
Historic Downtown Winter Garden300 W Plant St, Winter Garden, FL 34787 · 12.7 mi approx. from OrlandoDirections
All ages; stroller-friendly historic brick main street with barrier-free sidewalks
FreeFree public community festival and nightly holiday lighting displays
About this adventure
Historic Downtown Winter Garden glows during its month-long holiday celebration along Plant Street. Over one million lights transform City Hall, the clock tower, and the charming brick-lined streets into an idyllic holiday postcard, featuring a 25-foot animated holiday tree at Centennial Plaza. Children delight in strolling past decorated shop windows, listening to live street buskers and brass quartets, and taking horse-drawn carriage tours through the historic district. The pedestrian plaza around the splash pad offers wide sidewalks, ramped curb cuts, clean public restrooms, and family-friendly dining patios.
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