Community Events

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!

Click here to become a vendor at one of our Festival's or Farmers Market.

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!

Heritage Day Logo

Saturday, January 27, 2024
Speer Park
10-2 p.m.

Presented by Orlando Health and in partnership with Healthy West Orange and the Oakland Nature Preserve, celebrates Oakland’s small-town charm, unique history, nature, wellness and the arts with a family-friendly day of live music, food trucks, fine arts and crafts, quality vendors, interactive kids’ activities, and more.

Saturday, March 23, 2024
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.

Community Events

Town Events

Town of Oakland Farmers Market - 2nd & 4th Thursdays

Music Under the Oaks: A night of live Latin Jazz Music

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