The town of Oakland is one of the oldest municipalities in Orange County — established in 1887 — and once was a major center of commerce with a thriving downtown that included an opera house and many businesses. A devastating fire wiped out the downtown but not the town’s determination to forge on.
Today, Oakland continues to grow with more than 3,500 residents and an increasing commercial presence on Oakland Avenue and West Colonial Drive.
Oakland’s town commissioners, officials and residents will recognize that resolve to rebuild Saturday during the Oakland Heritage Day celebration in the town’s historic downtown area.
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 Healthy West Orange Arts & Heritage Center.
At the arts and heritage center, Westly's 6th Annual Virtual 5K in-person event kicks off 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.
Folks can do their part in preserving the town’s history by participating in a History Harvest. The town is hoping attendees will take their historic items relating to Oakland to the center from 10 a.m. to 1 p.m. to be donated, loaned or scanned.
The center’s art and history exhibit will celebrate black heritage in Florida and Oakland with a soft opening of a new exhibition, “Hold Fast to Dreams,” from 10 a.m. to 2 p.m. The art exhibit delves into the town’s black heritage, starting with the growing workforce after the Civil War of citrus, lumber and turpentine, and continuing through the arrival of the railroad and the refurbishing of the Historic African American Cemetery.
The exhibition also highlights many of Oakland’s black leaders, as well as families that have lived in the town for generations.
At 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 known for its residency at a local theme park. Food trucks will offer Burger Fi, Smoking Soul BBQ, Razzo’s Pizzeria and Hot Dog Therapy; and West Orange Creamery will have sweet treats, and a beer and wine garden.
The Oakland Nature Preserve is sponsoring Historic Florida, which will feature blacksmiths, animal ambassadors and a silent auction benefitting the preserve. Gatorland will bring live alligators, snakes and exotic reptile encounters.
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.
“Oakland Heritage Day at Speer Park has been a long-standing event that allows residents and attendees to enjoy the history, as well as all the arts and crafts, food, and beverages the vendors have to offer,” Oakland Mayor Kathy Stark said. “There will be bands, music and a hands-on educational offering from Gatorland Orlando. Runners can take part in Westly’s 6th Annual 5K held by Healthy West Orange.
“This event has a long history in Oakland and has gotten better year after year,” Stark said. “I always look forward to seeing residents I know and meeting new residents and attendees. Oakland has much to be proud of, and this is a great way to have fun and learn about our town at the same time.”