Oakland Heritage Day returns to celebrate town’s 135th anniversary

A day of fun and activities will pay tribute to the town’s extensive history during Oakland Heritage Day.

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Oakland Heritage Day returns this year to commemorate the town of Oakland’s 135th anniversary. The festival — set for 10 a.m. to 2 p.m. Saturday, Jan. 28, in historic downtown Oakland — will be revitalized with fresh, new experiences tailored for both longtime and new residents.
The event 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, vendors, interactive children’s activities, and more.
Activities will take place in two locations: Speer Park and the Health West Orange Arts & Heritage Center.


• 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 known for its residency at a local theme park.
• Food trucks including Burger Fi, Smoking Soul BBQ, Razzo’s Pizzeria and Hot Dog Therapy; sweet treats, 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.



• 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 at bit.ly/3JO7aT3.
• The Orlando Youth Chamber Ensemble will perform on the center porch from 11 a.m. to 2 p.m.
• Soul Haven Ranch will offer horse-drawn carriage tours beginning on Petris Avenue outside the center. Register at bit.ly/3X1QflF.
• 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, visit oaklandfl.gov/999/Community-Events.

The event is presented by Orlando Health in partnership with Healthy West Orange and the Oakland Nature Preserve.



Amy Quesinberry

Community Editor Amy Quesinberry was born at the old West Orange Memorial Hospital and raised in Winter Garden. Aside from earning her journalism degree from the University of Georgia, she hasn’t strayed too far from her hometown and her three-mile bubble. She grew up reading The Winter Garden Times and knew in the eighth grade she wanted to write for her community newspaper. She has been part of the writing and editing team since 1990.

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