Central Florida
Running in Winter Haven, FL
Your local guide to races, running stores, and the Winter Haven running community.
2
Upcoming Races
0
Running Stores
Running in Winter Haven at a Glance
wb_sunny Best Running Months
Oct – Apr
Cooler temperatures, lower humidity
thermostat Typical Weather
55–92°F
Year-round running climate
terrain Terrain
Flat
Road, trail, and beach routes
directions_run Popular Distances
5K & 10K
Most popular race distances
Fastest Winter Haven Runners, 2026 Cross Country
Season bests from 2 Winter Haven schools, pulled from the Florida XC database.
directions_run High School
Boys · 5k Full list
| 1 | Maxx De La Cruz '27 | 18:38.0 |
| 2 | Julius Hanford '27 | 18:43.2 |
| 3 | Devion Pinckney '27 | 19:54.8 |
| 4 | Jeremiah Elas '29 | 20:07.6 |
| 5 | Joel Villba All Saints'· 1A | 20:22.2 |
Girls · 5k Full list
| 1 | Charlotte Roy '31 All Saints'· 1A | 18:28.5 |
| 2 | Kylie Cook '31 All Saints'· 1A | 20:27.2 |
| 3 | Lindsey Cook '28 All Saints'· 1A | 20:48.3 |
| 4 | Melody Lopez '30 | 22:13.3 |
| 5 | Savannah Simonds '32 All Saints'· 1A | 22:27.7 |
Times are as run, on the course each athlete raced, so they are not course-adjusted. Regular season and postseason meets in the database only. Missing a school? Let us know.
Latest Winter Haven Running News
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Cross Country · September 1, 2026
Middle Schoolers Racing Varsity: Florida's Top 5 in Every Grade, Boys and Girls
An eighth grader finished second at the Kowboy behind the defending 2A state champion. A seventh grader won a varsity race outright in Cape Coral. Two sixth graders ended August one second apart without ever meeting. The top five middle schoolers in every grade, boys and girls, racing Florida high school cross country.
Cross Country · August 28, 2026
Kowboy XC Invitational Preview: Gateway and St. Cloud Return Everyone. Only One of Them Has Raced.
Gateway and St. Cloud both return all seven boys they ran in Kissimmee last August, and only one of them has been on a starting line in 2026. Boone's girls win every version of the math without running a step — and Arabella Duffell is entered with the meet record in reach.
Upcoming Races in Winter Haven
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Latest Running Articles
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Cross Country
Horse Park Recap: Mantecon Opens With the Win, Gaona-Zelaya Beats Hallick and Tomasic, and Destremps Goes Under Ten
11 min read
Local Guides
In Ocala for a Race? Make a Day of It
7 min read
Cross Country
Estero 3D Invitational, Run Through the Race Simulator: Fort Myers by 41, Aubrey Rogers by 29, and Both Individual Titles Flip With the Toggle
10 min read
Frequently Asked Questions About Running in Winter Haven
What running races are in Winter Haven, Florida? expand_more
Winter Haven currently has 2 upcoming running races. The next race is Warriors For Wellness 5k on October 3, 2026. Browse the events listed above for registration links and full race details.
Where can I buy running shoes in Winter Haven? expand_more
While there are no specialty running stores listed in Winter Haven yet, check our full Florida running store directory for the nearest options.
Are there running clubs or coaches in Winter Haven? expand_more
Winter Haven has an active running community. Check our full directory for local running clubs, coaches, and fitness groups near Winter Haven.
What distances can I race in Winter Haven? expand_more
Winter Haven typically hosts races across popular distances like 5K, 10K, half marathon, and marathon. Check the events section above for current availability.
What is the best time of year to run in Winter Haven, Florida? expand_more
The best running season in Winter Haven is October through April, when temperatures average 55–75°F with lower humidity. Summer months (June–September) are hot and humid, so runners should plan for early morning or evening runs and stay hydrated. Winter Haven currently has 2 races scheduled — most Florida races are concentrated in the cooler months.
Running in Winter Haven, Florida
Winter Haven is home to an active running community with 2 upcoming races this season. Whether you're training for your first 5K or chasing a marathon PR, Winter Haven has the roads, trails, and community to support your goals.
Browse all upcoming races in Winter Haven above, or view the full event calendar with filters for distance, surface, and race date. Running a race in Winter Haven? Submit your event to get listed for free.