Holiday Five (Five Days, Five Distances to choose from)
calendar_today December 27, 2026
location_on Winter Park, Central Florida
Half Marathon5K31 MilesMarathon +1 more
Central Florida
Running in Winter Park, FL
Your local guide to races, running stores, and the Winter Park running community.
9
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 & 10K
Most popular race distances
Fastest Winter Park Runners, 2026 Cross Country
Season bests from 5 Winter Park-area schools, including Maitland, pulled from the Florida XC database.
directions_run High School
Boys · 5k Full list
| 1 | Matteo Kirwan '29 Circle Christian· 1A | 15:59 |
| 2 | Jonah Lehman-Saba '28 Circle Christian· 1A | 16:20 |
| 3 | Aschalew Parker '27 Circle Christian· 1A | 16:43 |
| 4 | Jackson Palk '29 Winter Park· 4A | 16:48.6 |
| 5 | Lucas Le Douran '28 | 17:10.5 |
Girls · 5k Full list
| 1 | Kathryn Ryan '29 Winter Park· 4A | 19:07 |
| 2 | Bella Sacks '27 Winter Park· 4A | 19:25.9 |
| 3 | Sofia Siddiqi '27 Winter Park· 4A | 20:02.4 |
| 4 | Kaitlyn Conboy '32 Circle Christian· 1A | 20:07.0 |
| 5 | Emmanuelle DelVecchio '28 | 20:44.7 |
directions_run Middle School
Boys · 3k Full list
| 1 | Mateu Fernandes '31 | 10:53.6 |
| 2 | Andrew Goodhue '32 | 12:27.8 |
| 3 | Silas MARONICK '31 Circle Christian· 1A | 13:03.01 |
| 4 | Garrett Struyk '33 | 13:07.4 |
| 5 | Daniel Rezende '31 Circle Christian· 1A | 13:09 |
Girls · 3k Full list
| 1 | Hannah BECK '32 Circle Christian· 1A | 14:44.7 |
| 2 | Jordan LEGGERIO '33 Circle Christian· 1A | 14:56.71 |
| 3 | Martha Brown '32 | 15:48.8 |
| 4 | Paige Bryant '33 Circle Christian· 1A | 16:39.60 |
| 5 | Kelsey Schwab '33 | 18:23.7 |
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 Park Running News
All news →
Cross Country · October 12, 2026
Weekend Recap: Pre-State Is Off, Episcopal Wins JAC, Sallault and Thompson Roll, and LaBelle Takes the Sugar Run at Clewiston
Thursday through Saturday, October 8 to 10, meet by meet: with Pre-State canceled for Hurricane Isaias, Episcopal's girls won the JAC Invitational over Bishop Kenny and Nease as Jillian Jakab won the race, Axel Sallault and Quentin Thompson won at South Marion and Wildwood, Spanish River swept the individual titles at Snake Bite while Columbus won the boys' team race, Bolles was eighth in the Eastern States Championship at Manhattan, and LaBelle won the boys' title at the Clewiston XC Sugar Run Invite, with photos from Dr. Bob Cooke.
Cross Country · October 4, 2026
Weekend Recap: Mantecon Wins Great American in 14:35, Moss and McMenemy-Hoang Take flrunners, Ross Runs 15:59 as Ponte Vedra Edges Vanguard at Speziale
Thursday through Saturday, October 1 to 3, meet by meet: Marcelo Mantecon of Belen Jesuit wins the COROS Race of Champions at the Great American XC Festival in Cary in 14:35.9, the fastest time by a Florida boy this season, with Armando Cruz sixth and Belen second of 40 teams on a hilly, humid morning that slowed the rest of the Florida contingent. Will Moss and Eva McMenemy-Hoang win the Race of Champions titles at flrunners.com in Lakeland and Fort Myers and Chiles take the team races, Luke Ross runs 15:59 as Ponte Vedra beats Vanguard twice at the Craig Speziale Invitational, Jaxon Kiper returns with a 15:24 at Don Bishop, Brody Johnson beats Luis Rivera by half a second at Harmony, Lainee Mercer runs 18:24 at Wild Bulldog, and Madison Muller stays unbeaten at Venice. David Barton of Maclay runs a 22-second personal best of 15:28 at the Alexander Invitational in Georgia. Bishop Kenny's girls are 16th of 44 in the Nike XC Town Twilight Race of Champions in Indiana. Twenty-six meets and more than 20,800 results.
Cross Country · September 23, 2026
Florida's Top Seventh-Grade Cross Country Runners: Boys and Girls Top 5
Colette Heffernan is unbeaten and the No. 1 middle school girl in Florida in any grade. The boys' top four project within four seconds of each other. The top five seventh-grade boys and girls in the state, from middle school 3ks and high school 5ks alike.
Cross Country · September 19, 2026
Weekend Recap: Sallault Runs 15:05 at Hawks on the Hill, Eudaly and Rivera Take North Port, Spanish River Names Its Course, and Belen Goes 1-2-3 in Alabama
Friday and Saturday, September 18 and 19, meet by meet: Axel Sallault runs 15:05.9 at Hawks on the Hill with Quentin Thompson 23 seconds back, Katherine Eudaly takes 63 seconds off her best to win North Port in 17:37 and Luis Rivera beats three ranked 3A runners, and Spanish River's seniors win both Race of Champions titles on the course that now carries Rick Rothman's name. Madison Muller and Lyla Hallick win again, Vanguard scores 22 at Rockledge, Hagerty holds off Tavares, and a seventh grader wins the Bulldog. Then Florida on the road: Belen Jesuit goes 1-2-3 at the Southern Showcase, IMG Academy's girls win it with Niceville second, Bolles takes second and seventh at the adidas XC Challenge, and Nease puts five under 16:07 at Roy Griak. Updated Sunday with the Katie Caples Invitational, where Annabella Tomasic ran 17:24 and Bishop Moore beat Bishop Kenny by a point, and Running on the Range, where Drake Matyka handed RJ Destremps his first loss.
Upcoming Races in Winter Park
See all events →directions_run
Winter Park 50K, Marathon, Half, 10K & 5K – MileBuilt Cady Way Bridge 2-Day Challenge
calendar_today February 20, 2027
location_on Winter Park, Central Florida
50KMarathonHalf Marathon10K +1 more
directions_run
Sunshine Double (Two Days, Five Distances to choose from)
calendar_today May 1, 2027
location_on Winter Park, Central Florida
Marathon31 MilesHalf Marathon10K +1 more
directions_run
Winter Park 50K, Marathon, Half, 10K & 5K – MileBuilt Cady Way Bridge Memorial Day 3-Day Challenge
calendar_today May 29, 2027
location_on Winter Park, Central Florida
50K10K5KMarathon +1 more
Independence Double (Two Days, Five Distances to choose from)
calendar_today June 26, 2027
location_on Winter Park, Central Florida
Half Marathon31.06 Miles10KMarathon +1 more
Frequently Asked Questions About Running in Winter Park
What running races are in Winter Park, Florida? expand_more
Winter Park currently has 9 upcoming running races across distances including Half Marathon, 5K, 31 Miles, Marathon, 10K. The next race is Holiday Five (Five Days, Five Distances to choose from) on December 27, 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 7 distances: Half Marathon, 5K, 31 Miles, Marathon, 10K, 50K, 31.06 Miles. 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 9 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 9 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 see every upcoming race in Winter Park with filters for distance, surface, and race date. Running a race in Winter Park? Submit your event to get listed for free.