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, December 3, 2022 
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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Saturday, January 28, 2023
Speer Park
10-2 p.m.

The 23rd annual Oakland Heritage Day presented by Orlando Health returns in January 2023 with a day of music, arts & craft vendors, historic tours, and community. The day will start with 5k sponsored by Healthy West Orange, beginning at The Arts & Heritage Center towards the Oakland Nature Preserve and ending at Speer Park at the Oakland Heritage Day Festival.

Saturday, March 25, 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. 

  1. ‘Among the Oaks’: Oakland celebrates trees with new art and history exhibit

    Commemorating nearly two decades as a Tree City USA®, Oakland is hosting a special art and history exhibit celebrating the beauty of nature and delving into the inspiration behind Oakland’s name. Read on...
  2. Santa rolls into Oakland on Dec. 3 for ‘Santa’s Lane’

    Offering exciting experiences and classic holiday joy, the Town of Oakland is thrilled to announce “Santa’s Lane” is returning bigger and jollier than ever. Read on...
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