# Things to do with kids at Historic Downtown Winter Garden

> 4 upcoming family events and 0 ongoing programs and visits at Historic Downtown Winter Garden, 300 W. Plant Street, Winter Garden, FL 34787, in the Orlando–Kissimmee–Sanford area. Dates and times are Eastern Time. Today is Wed, Nov 11.

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/venues/historic-downtown-winter-garden

## Events ahead

- [Main Street Holiday Stroll in Downtown Winter Garden](https://grassyknees.com/orlando/activities/main-street-holiday-stroll-in-downtown-winter-garden--listing-cf6c7e4214939e3b44fabe79) — Dec 3 – Jan 3 · Historic Downtown Winter Garden · Free · checked Nov 3. 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…
- [A Merry Winter Garden Light Up & Holiday Stroll](https://grassyknees.com/orlando/activities/a-merry-winter-garden-light-up-and-holiday-stroll--listing-770349598d70f15700acd48d) — Dec 4 – Jan 3 · 6:00 PM – 9:00 PM · Historic Downtown Winter Garden · All ages · Free · checked Nov 7. 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…
- [Light Up Winter Garden](https://grassyknees.com/orlando/activities/light-up-winter-garden--listing-0813490b2eaef1a11ff1c2b0) — Fri, Dec 4 · 6:00 PM – 9:00 PM · Historic Downtown Winter Garden · Free · checked Oct 14. Winter Garden's annual tree-lighting ceremony kicks off 31 days of 'Tis the Season events downtown, with A Very Merry Light Show, live holiday entertainment, a children's snow…
- [Winter Garden Christmas Parade](https://grassyknees.com/orlando/activities/winter-garden-christmas-parade--listing-0c9bebe9ae04713fafeea86f) — Sat, Dec 5 · 10:00 AM – 11:00 AM · Historic Downtown Winter Garden · Free · checked Oct 14. Winter Garden's annual Christmas Parade through historic downtown with festive floats, community groups, holiday entertainment and Santa Claus. Bring lawn chairs and blankets…

## Nearby

- [Things to do with kids in Winter Garden, FL](https://grassyknees.com/orlando/towns/winter-garden-fl) (Markdown: https://grassyknees.com/orlando/towns/winter-garden-fl.md)
- More venues in Winter Garden, FL: [Horizon West Branch Library](https://grassyknees.com/orlando/venues/horizon-west-branch-library) (Markdown: https://grassyknees.com/orlando/venues/horizon-west-branch-library.md), [Garden Theatre on Plant](https://grassyknees.com/orlando/venues/garden-theatre-on-plant) (Markdown: https://grassyknees.com/orlando/venues/garden-theatre-on-plant.md), [Downtown Interactive Fountain & Pavilion](https://grassyknees.com/orlando/venues/downtown-interactive-fountain-and-pavilion) (Markdown: https://grassyknees.com/orlando/venues/downtown-interactive-fountain-and-pavilion.md)
- [Things to do with kids in Orlando](https://grassyknees.com/orlando) (Markdown: https://grassyknees.com/orlando.md)
- [This weekend in Orlando](https://grassyknees.com/orlando/this-weekend) (Markdown: https://grassyknees.com/orlando/this-weekend.md)

Venue pages are listed once a venue has 3 current listings.