Saturday: Celebrate Oakland’s 135th anniversary at Heritage Day

Heritage Day returns this weekend to the town of Oakland in west Orange County.


This year’s festival will be held on Saturday, Jan. 28 in Oakland’s historic downtown.

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Organizers said the event will celebrate Oakland’s 135th anniversary and will feature “fresh new experiences tailored for both longtime and new residents.”

Visitors can experience small-town charm while enjoying arts and crafts, live music, kids’ activities and various vendors.

Food trucks will include Burger Fi, Smoking Soul BBQ, Razzo’s Pizzeria, and Hot Dog Therapy.

A beer and wine garden will be located near the West Orange Creamery.

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Organizers added that other festival highlights will include:

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.

  • Historic Florida section: Sponsored by Oakland Nature Preserve, featuring animal ambassadors and a silent auction benefitting the Preserve.

  • Gatorland’s live show: Features alligators, snakes, and exotic reptile encounters.

  • Orange Blossom Market: Features boutique vendors; for a full list, click here.

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Healthy West Orange Arts & Heritage Center:
  • Westly’s 6th Annual Virtual 5K: The in-person event kicks off at 9 a.m. To register, click here.

  • The Orlando Youth Chamber Ensemble: Presented by HAPCO, performs from 11 a.m. – 2 p.m.

  • The Center’s art and history exhibit: “Hold Fast to Dreams” celebrates Black heritage.

  • History Harvest: Participate by bringing historic items relating to Oakland to be donated, loaned, or scanned.

  • Historic horse-drawn carriage tours: To register, click here.

Oakland Heritage Day runs from 10 a.m. to 2 p.m. on Jan. 28

For complete event details, click here.

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