Community Events

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The Town of Oakland welcomes the community to join us at our unique festivals and events. From a helicopter Easter Egg Drop to free concerts along the trail, Town events large and small add to the unique character and small-town charm of Oakland.

Save the date for our signature festivals listed below. View the calendar and news releases for information on additional upcoming special events. We hope to see you soon!

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Saturday, January 28, 2023
Speer Park
10-2 p.m.

Oakland Heritage Day presented by Orlando Health and in partnership with Healthy West Orange and the Oakland Nature Preserve, returns in 2023 to commemorate Oakland’s 135th anniversary. The time-honored festival will be revitalized with fresh, new experiences tailored for both longtime and new residents alike.

Saturday, April 1, 2023
VanderLey Park
10-1 p.m.

Oakland’s annual springtime time event in VanderLey Park features an egg hunt, petting zoo, and family friendly fun. While there, pose with the Easter Bunny and hop down the West Orange Trail to additional fun at The Healthy West Orange Arts & Heritage Center. 

Santa Logo

Saturday, December 2, 2023 
Historic Town Center Circle 
3-6 p.m. 

Historic Town Center at Tubb Street will transform into “Santa’s Lane,” bringing the North Pole to West Orange. Come visit Santa and his elves and stay for snow flurries and family fun! 


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