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

OAKLAND, Fla. — Heritage Day returns this weekend to the town of Oakland in west Orange County.

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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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