Wed
27
May
Boogie Nights Summer Run Series - Ventura
Ventura, US
Wed
27
May
Hike For a Change 2026
Duxbury, US
Wed
27
May
Johnnycake Jolt Series!
Windsor Mill, US
Wed
27
May
JPMorganChase Corporate Challenge New York City
New York, US
Wed
27
May
Mighty Mile - FREE RACE FOR KIDS - Dansville
Dansville, US
Wed
27
May
Oviedo Memorial 5K
Oviedo, US
Wed
27
May
Palmetto Dunes Turtle Trot 5K
Hilton Head Island, US
Wed
27
May
Parks Foundation of Hendricks County: Summer Fun Run & Walk Series
Danville, US
Wed
27
May
Rock Dallas Trail Run Half Marathon, 15K & 5K
Dallas, US
Wed
27
May
05/27 Move 2026 Champ
Cincinnati, US
Wed
27
May
05/27 Move 2026 Volunteer
Cincinnati, US
Wed
27
May
CCSF Color Rush
Cedarburg, US
Wed
27
May
Firefly 5K
Wilmington, US
Wed
27
May
Lighthouse 5k Series May 27, 2026
Corolla, US
Wed
27
May
Lisa's Rainbow Rockin 5.27K
Steger, US
Wed
27
May
One Hour Track Run
Alexandria, US
Wed
27
May
Senior Field Trip to SF Giants Game
Daly City, US
Wed
27
May
TCTC Summer Track Series
Winston-Salem, US
Thu
28
May
NYU Langone Health HYROX New York
New York, US
Thu
28
May
FitzGerald Elementary 8th Annual Fitzy 5k Fun Run/Walk
Waltham, US
Holiday Five
Tuesday, December 29, 2026 · Winter Park, United States
Distances
5K
10K
Half
Full
49.9km
About this race
Holiday Five is a small race series in Winter Park, starting at 6:00 AM EST, offering 50K, marathon, half marathon, 10K, and 5K distances. The field is typically small, ranging from 1 to 100 participants, giving it the feel of a low-key local event rather than a large production.
The races take place on a paved, partly shaded bike path within an urban environment. The course is fast and flat, with average temperatures between 53 and 72 degrees. Easy parking and a generous time limit make it accessible for first-time participants, casual runners, and those seeking a straightforward race experience.
Start location
Cady Way Trail Head
Winter Park, FL