Westly's 9th Annual 5k
Thursday, January 1 – Saturday, January 31, 2026
Past event
9:30 AM EST
Oakland, Florida
Free · 2 races
5km
Event summary
Get ready to kick off the new year with an exciting fitness challenge at Westly's 9th Annual 5K! This vibrant event will take place in Oakland, Orange, throughout January 2026, with the exhilarating in-person race happening on Saturday, January 31. Join fellow community members at the Healthy West Orange Arts & Heritage Center as you run or walk the scenic 3.1-mile course along the West Orange Trail. Check-in starts at 8:00 AM, followed by warm-ups at 9:15 AM, and the race will commence at 9:30 AM.
Whether you prefer to participate in person or opt for the virtual 5K, this event is designed for everyone! For those who can't join on the 31st, you can complete the 5K challenge at your own pace anywhere between January 1 and 31. Enjoy the camaraderie, receive a T-shirt and medal for in-person participants, and take part in an array of fun activities at the Fresh Start Zone in Speer Park after the race. With live music, food trucks, and wellness activities, there's something for everyone in this celebration of health and community spirit. Don't miss out on this fantastic opportunity to get active and connect
Whether you prefer to participate in person or opt for the virtual 5K, this event is designed for everyone! For those who can't join on the 31st, you can complete the 5K challenge at your own pace anywhere between January 1 and 31. Enjoy the camaraderie, receive a T-shirt and medal for in-person participants, and take part in an array of fun activities at the Fresh Start Zone in Speer Park after the race. With live music, food trucks, and wellness activities, there's something for everyone in this celebration of health and community spirit. Don't miss out on this fantastic opportunity to get active and connect
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Races
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Westly's 9th Annual 5k (In-Person)
Entries closedSaturday, Jan 31, 2026 (9:30 AM EST)
Free
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Westly's 9th Annual 5k (Virtual)
VirtualComplete Westly's Annual Virtual 5K anytime in the month of January!
Entries closedThursday, Jan 1, 2026 (9:30 AM EST)
Free
Organiser's description
New year, new miles - come snag yours at our free 5K! Were getting active together as a community in person AND virtually! Register for one, or both (must register separately for each) if you want double the 5K fun!
* Please note the prize details below, as some of our guidelines have changed.
In-Person 5K Option:
Want to complete 3.1 miles with an awesome group? Join us on Saturday, January 31 along the West Orange Trail! Walk or run a 5K as a community. All ages are welcome! The race will begin at the Healthy West Orange Arts & Heritage Center at the Town of Oakland, with check-in at 8:00am, warm-ups at 9:15am, and race kick off at 9:30am.
After you cross the finish line, head over to Oaklands Speer Park where Healthy West Orange will host our Fresh Start Zone at Oakland Heritage Day! Our local partners will be offering fitness, nutrition, and wellbeing activities for FREE from 10am 2pm. Folks can also enjoy live music, food trucks, and artisan vendors.
Virtual 5K Option:
Cant make it on the 31st? No worries! Heres how our virtual 5K works: register first, then complete 3.1 miles between January 1-31 at your own pace, wherever you like, whenever you like. Bike the West Orange Trail, hike at Oakland Nature Preserve, rollerblade around your neighborhood! If you want to break it up into segments go for it! Tell your family and friends, because its open to all ages and mobility levels.
No need to track your miles we go by the honor system and are here to encourage you to get moving. We always love it when folks send in their finish line photos if they complete their 5K virtually! Post your photos and tag or DM us on social media @healthywestorange, or email us at [email protected]
5K Prize Info:
In-Person 5K T-shirts and Medals:
This year, 5K T-shirts will be handed out first come, first served at the In-Person 5K on January 31 starting at 8am. Specific sizes are not able to be reserved/guaranteed, as there are limited quantities. Medals will be distributed to participants at the finish line!
Virtual 5K T-shirts:
T-shirt pickup for virtual participants will take place on Thursday, February 5 from 4pm to 7pm at the Healthy West Orange Building at 1200 E Plant St, Winter Garden. It is first come, first served, with limited quantities, and specific sizes are not guaranteed. We are unfortunately unable to guarantee new medals to virtual participants, however assorted medals from years past will be available at pickup.
Please note: Prizes are limited to residents of the following zip codes: 32703; 32710; 32808; 32810; 32818; 32819; 32821; 32830; 32835; 32836; 34734; 34740; 34760; 34761; 34786; 34787.
* Please note the prize details below, as some of our guidelines have changed.
In-Person 5K Option:
Want to complete 3.1 miles with an awesome group? Join us on Saturday, January 31 along the West Orange Trail! Walk or run a 5K as a community. All ages are welcome! The race will begin at the Healthy West Orange Arts & Heritage Center at the Town of Oakland, with check-in at 8:00am, warm-ups at 9:15am, and race kick off at 9:30am.
After you cross the finish line, head over to Oaklands Speer Park where Healthy West Orange will host our Fresh Start Zone at Oakland Heritage Day! Our local partners will be offering fitness, nutrition, and wellbeing activities for FREE from 10am 2pm. Folks can also enjoy live music, food trucks, and artisan vendors.
Virtual 5K Option:
Cant make it on the 31st? No worries! Heres how our virtual 5K works: register first, then complete 3.1 miles between January 1-31 at your own pace, wherever you like, whenever you like. Bike the West Orange Trail, hike at Oakland Nature Preserve, rollerblade around your neighborhood! If you want to break it up into segments go for it! Tell your family and friends, because its open to all ages and mobility levels.
No need to track your miles we go by the honor system and are here to encourage you to get moving. We always love it when folks send in their finish line photos if they complete their 5K virtually! Post your photos and tag or DM us on social media @healthywestorange, or email us at [email protected]
5K Prize Info:
In-Person 5K T-shirts and Medals:
This year, 5K T-shirts will be handed out first come, first served at the In-Person 5K on January 31 starting at 8am. Specific sizes are not able to be reserved/guaranteed, as there are limited quantities. Medals will be distributed to participants at the finish line!
Virtual 5K T-shirts:
T-shirt pickup for virtual participants will take place on Thursday, February 5 from 4pm to 7pm at the Healthy West Orange Building at 1200 E Plant St, Winter Garden. It is first come, first served, with limited quantities, and specific sizes are not guaranteed. We are unfortunately unable to guarantee new medals to virtual participants, however assorted medals from years past will be available at pickup.
Please note: Prizes are limited to residents of the following zip codes: 32703; 32710; 32808; 32810; 32818; 32819; 32821; 32830; 32835; 32836; 34734; 34740; 34760; 34761; 34786; 34787.
Location
126 W. Petris Ave, Oakland, 34760, FL, United States
Westly's 9th Annual 5k
Event data
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