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Thu January 1 - Sat January 31, 2026
Oakland, FL 34760 US Directions

Events

Westly's 9th Annual 5K (In-Person)

Price: $0
Date Range: 01/31
Time: 9:30AM EST 11:00AM EST
Registration ends December 31, 2025 at 9:30am EST

Westly's 9th Annual 5K (Virtual)

Price: $0
Registration ends January 31, 2026 at 11:59pm EST

Place

126 W. Petris Ave
Oakland, FL US 34760

Description

New year, new miles - come snag yours at our free 5K! We’re 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 Oakland’s 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:

Can’t make it on the 31st? No worries! Here’s 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 it’s 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 info@healthywestorange.org 

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.

Race Contact Info

If you have any questions about this race, please contact the race director at

Directions

Race Participant Survey

Please complete the following survey to help us better understand your race experience.

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