
5K with the 5-0
About This Event
**Run with the Oakland Police Department along the West Orange Trail. All proceeds will benefit the Oakland Police Department Community Programs. **
Event Timeline:
Friday, November 20, 2026: Packet pick up at Oakland Police Department from 4:00 PM to 6:00 PM.
Saturday, November 21, 2026: Packet pick up at Oakland Police Department from 6:30 AM to 7:30 AM.
Race START time: 8:00 AM
Parking:
Parking for the 5K will be at Oakland Charter School, located at 456 E. Oakland Ave. Oakland, FL 34760.
Downtown Oakland 230 N. Tubb St Oakland, FL 34760
Handicap Parking at Oakland Charter School, 456 E. Oakland Ave.456 E. Oakland Ave. Oakland FL 34760
Vendors:
Will Set Up in Police Department Parking Lot 540 E. Oakland Ave. Oakland, FL 34760
Route:
Run will start on the Entrance to the Oakland Police Department. You will run North on Winter Landing Dr. to the West Orange Trails, then Westbound on the West Orange Trails through Scenic Oakland, to the Oakland Nature Preserve Entrance. You will then turn around at the entrance to the Oakland Nature Preserve and return to the Oakland Police Department Finish Line.
Water Stations:
There will be a water station at the one (1) mile marker and two (2) mile marker.
AWARDS:
All Finishers will receive a Finisher Medal.
Awards will be awarded to the Top Three in Each Age Group.
VIRTUAL RUN:
If you are running or walking the virtual 5K, you will have until November 29, 2026, to enter your results.
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Weather
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November 21, 2026