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.
The festival 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.
It will be held on Saturday, Jan. 28 from 10 a.m.-2 p.m. in Historic downtown Oakland.
Speer Park
• The Gerry Williams Band, a funk, soul, and R&B act, headlines the festival, with additional performances by soloist Kelly Jarrard and Handpicked, a banjo trio beloved for their residency at an Orlando theme park.
• Food trucks including Burger Fi, Smoking Soul BBQ, Razzo’s Pizzeria, and Hot Dog Therapy; sweet treats and beer and wine garden by West Orange Creamery.
• Historic Florida section sponsored by Oakland Nature Preserve featuring blacksmiths, animal ambassadors and a silent auction benefitting the Preserve.
• Gatorland’s live alligators, snakes, and exotic reptile encounters.

Healthy West Orange Arts & Heritage Center
• Westly’s 6th Annual Virtual 5K In-Person Event kicks off from the Healthy West Orange Arts and Heritage Center at 9 a.m. and continues to the Healthy West Orange Fresh Start Zone at Speer Park. Register here: https://runsignup.com/Race/FL/Oakland/WestlysAnnualV5K
• The Orlando Youth Chamber Ensemble will perform on the Center porch from 11 a.m. – 2 p.m.
• Soul Haven Ranch will offer historic horse-drawn carriage tours beginning on Petris Avenue outside the Center. Register here: https://www.soulhavenranch.com/historic-carriage-tour
• Participate in a History Harvest by bringing historic items relating to Oakland to be donated, loaned or scanned at the Center.
• The Center’s art and history exhibit will celebrate African American heritage in Florida and Oakland.

For more information on Oakland Heritage Day, visit oaklandfl.gov/999/Community-Events or follow the Town on Facebook at www.facebook.com/oaktownusa.