Top Downtown Events

Spring Fever in the Garden_Text.png

The Spring Fever in the Garden festival is the main fundraising activity for the Bloom & Grow Garden Society of West Orange county Florida. Our mission statement:
“To stimulate a knowledge and love of gardening; To aid in protection of native plants and birds; To encourage civic plantings”.

Blues and BBQ Fest

Blues and BBQ is a great night of delicious food and rockin' music held in Downtown Winter Garden! Its always a great time!

Happy of 4th July

4th of July Downtown Winter Garden Fireworks




Drive, stroll, shop, dine and bicycle while enjoying an all new Socially Distanced Halloween Experience from Friday, October 23 – Sunday, November 1, 2020. Please visit www.cwgdn.com for additional information and updates.

Cruz N' Car Show

Come out and enjoy approximately 275 classic cars of all makes and models will adorn the streets of downtown Winter Garden. All car enthusiasts and families will have so much to enjoy! Entertainment by WJBJ Cruisin' with the Classics.

Light Up

Winter Garden

Join us in welcoming the season with this annual event. Enjoy live entertainment, vendors, shopping and children’s activities.

Tis the Season 2018.png

Downtown Winter Garden is a great time for the entire family during the Christmas holidays!


In Downtown Winter Garden the Rotary Club of Winter Garden held a beautiful evening at Newton Park listening to the Orlando Philharmonic Orchestra.

Health and Harvest Fest

Health and Harvest Festival.jpg

Health screenings - Healthy cooking demos - Family bike ride

- Fun Activities for kids - Zumba and yoga


Memorial Day

Screen Shot 2020-07-24 at 4.15.17 PM.png

Paint, hide and find cool rocks in Winter Garden