Central Florida
Running in Winter Park, FL
Your local guide to races, running stores, and the Winter Park running community.
6
Upcoming Races
0
Running Stores
Running in Winter Park 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
Most popular race distances
Fastest Winter Park Runners, 2026 Cross Country
Season bests from 4 Winter Park schools, pulled from the Florida XC database.
directions_run High School
Boys · 5k Full list
| 1 | Matteo Kirwan '29 Circle Christian· 1A | 16:34.0 |
| 2 | Jackson Palk '29 | 17:06.0 |
| 3 | Aschalew Parker '27 Circle Christian· 1A | 17:19.0 |
| 4 | Joanh Lehman-Saba Circle Christian· 1A | 17:42.0 |
| 5 | Lucas Le Douran '28 | 17:57.1 |
Girls · 5k Full list
| 1 | Bella Sacks '27 | 19:33.1 |
| 2 | Kathryn Ryan '29 | 19:37.9 |
| 3 | Kaitlyn Conboy '32 Circle Christian· 1A | 20:07.0 |
| 4 | Emmanuelle DelVecchio '28 | 20:44.7 |
| 5 | Sofia Siddiqi '27 | 21:13.6 |
directions_run Middle School
Girls · 3k Full list
| 1 | Jordan LEGGERIO Circle Christian· 1A | 14:57.8 |
| 2 | Hannah BECK '32 Circle Christian· 1A | 15:36.6 |
| 3 | Claire CHEGWIN Circle Christian· 1A | 21:11.4 |
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.
Upcoming Races in Winter Park
See all events →directions_run
MileBuilt 2-Day Bridge Challenge
calendar_today February 20, 2027
location_on Winter Park, Central Florida
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Frequently Asked Questions About Running in Winter Park
What running races are in Winter Park, Florida? expand_more
Winter Park currently has 6 upcoming running races across distances including 5K. The next race is Labor Day Triple on September 5, 2026. Browse the events listed above for registration links and full race details.
Where can I buy running shoes in Winter Park? expand_more
While there are no specialty running stores listed in Winter Park yet, check our full Florida running store directory for the nearest options.
Are there running clubs or coaches in Winter Park? expand_more
Winter Park has an active running community. Check our full directory for local running clubs, coaches, and fitness groups near Winter Park.
What distances can I race in Winter Park? expand_more
Runners in Winter Park can choose from 1 distance: 5K. Whether you're looking for a quick 5K or training for a longer event, Winter Park has options for every level.
What is the best time of year to run in Winter Park, Florida? expand_more
The best running season in Winter Park 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 Park currently has 6 races scheduled — most Florida races are concentrated in the cooler months.
Running in Winter Park, Florida
Winter Park is home to an active running community with 6 upcoming races this season. Whether you're training for your first 5K or chasing a marathon PR, Winter Park has the roads, trails, and community to support your goals.
Browse all upcoming races in Winter Park above, or view the full event calendar with filters for distance, surface, and race date. Running a race in Winter Park? Submit your event to get listed for free.