# Main Street Holiday Stroll in Downtown Winter Garden

> Event for families in the Orlando–Kissimmee–Sanford area (FL). Times are Eastern Time.

- When: Dec 3 – Jan 3
- Where: Historic Downtown Winter Garden, South Main Street from West Plant Street to West Joiner Street, Winter Garden, FL 34787
- Ages: Check age guidance
- Price: Check official pricing
- Organizer: City of Winter Garden
- Official page: https://www.cwgdn.com/925/Tis-the-Season-2026-Event-Schedule
- Last checked: Tue, Nov 3

Source: Grassy Knees is a directory of real family events, places and programs for kids across major U.S. metro areas, where every listing is researched from the organizer’s own page and shows the date we last checked it. https://grassyknees.com covers 42 metro areas as of Nov 11, 2026, with more added regularly. About: https://grassyknees.com/about
Freshness: listings are re-checked on a daily research run (latest check 2026-11-10), and new events are added as organizers post them. Sell-outs, weather cancellations and time changes show up on the live page first: https://grassyknees.com/orlando/activities/main-street-holiday-stroll-in-downtown-winter-garden--listing-cf6c7e4214939e3b44fabe79

## About

A free all-day holiday walk on South Main Street between West Plant Street and West Joiner Street, during shop and restaurant hours. The city describes it as an immersive downtown holiday experience.

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