# A Merry Winter Garden Light Up & Holiday Stroll

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

- When: Dec 4 – Jan 3 · 6:00 PM – 9:00 PM
- Where: Historic Downtown Winter Garden, 300 W Plant St, Winter Garden, FL 34787
- Ages: All ages; stroller-friendly historic brick main street with barrier-free sidewalks
- Price: Free public community festival and nightly holiday lighting displays
- Organizer: City of Winter Garden
- Official page: https://www.cwgdn.com/916/Main-Street-Holiday-Stroll-2026
- Last checked: Sat, Nov 7

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/a-merry-winter-garden-light-up-and-holiday-stroll--listing-770349598d70f15700acd48d

## About

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.

## Similar picks in Orlando

- [A Merry Winter Garden Light Show](https://grassyknees.com/orlando/activities/a-merry-winter-garden-light-show--listing-1abcb5d7a305ae5c9a835cc0) — Sat, Dec 5 (+9 more dates) · 6:00 PM – 9:00 PM · Winter Garden City Hall · Free · checked Oct 14. An animated holiday light show synchronized to music across Winter Garden City Hall, described by the city as a must-see for all ages.
- [Lake Eola Park Christmas Tree Lighting & Wonderfall Light Show](https://grassyknees.com/orlando/activities/lake-eola-park-christmas-tree-lighting-and-wonderfall-light-show--listing-47620ada1797b9d999507c3c) — Dec 4 – Jan 6 · 5:00 PM – 10:00 PM · Lake Eola Park · All ages · Free · checked Nov 4. Downtown Orlando kicks off the holidays at Lake Eola Park with the illumination of the city's 72-foot Christmas tree adorned with 88,000 animated LED lights and 2,000 holiday…
- [The Santa Experience & Holiday Lights at ICON Park](https://grassyknees.com/orlando/activities/the-santa-experience-and-holiday-lights-at-icon-park--listing-1ffc76e5abe9bebfbca4600d) — Nov 13 – Dec 24 · 10:00 AM – 10:00 PM · ICON Park · All ages · With admission · checked Nov 7. ICON Park on International Drive transforms into a 20-acre holiday village centered around the 400-foot-tall observation wheel, which illuminates the night sky with a…
- [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…
- [Light Up the Holidays at Cranes Roost Park — Altamonte Springs](https://grassyknees.com/orlando/activities/light-up-the-holidays-at-cranes-roost-park-altamonte-springs--listing-adcb48e5ee94eeceb33e7a91) — Sat, Dec 5 · 5:00 PM – 9:00 PM · Cranes Roost Park, Altamonte Springs · Free · checked Oct 24. Altamonte Springs opens its holiday season with an evening at Cranes Roost Park, presented by the city and Duke Energy. The program includes live music and festive entertainment…
- [Light Up Venetian Gardens and Christmas Boat Parade — Leesburg](https://grassyknees.com/orlando/activities/light-up-venetian-gardens-and-christmas-boat-parade-leesburg--listing-87ec9c0e38f180281b54621b) — Sun, Dec 6 · 5:00 PM – 8:00 PM · Ski Beach Park (Venetian Gardens), Leesburg · Free · checked Oct 27. The City of Leesburg opens its holiday season on the Lake Harris shoreline with Light Up Venetian Gardens at Ski Beach Park, the lakefront section of Venetian Gardens. The…

## More for families

- [Things to do with kids at Historic Downtown Winter Garden](https://grassyknees.com/orlando/venues/historic-downtown-winter-garden) (Markdown: https://grassyknees.com/orlando/venues/historic-downtown-winter-garden.md)
- [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)
- [Things to do with kids in Orange County, FL](https://grassyknees.com/orlando/counties/orange-county-fl) (Markdown: https://grassyknees.com/orlando/counties/orange-county-fl.md)
- [Christmas lights and holiday events for kids in Orlando](https://grassyknees.com/orlando/christmas) (Markdown: https://grassyknees.com/orlando/christmas.md)
- [Things to do with kids in Orlando — December 2026](https://grassyknees.com/orlando/events/2026-12) (Markdown: https://grassyknees.com/orlando/events/2026-12.md)
- [This weekend in Orlando](https://grassyknees.com/orlando/this-weekend) (Markdown: https://grassyknees.com/orlando/this-weekend.md)
- [Things to do with kids in Orlando](https://grassyknees.com/orlando) (Markdown: https://grassyknees.com/orlando.md)