Cycling & running events in Orlando, 2026

Orlando Training Notes

Running: Locals run Lake Eola laps when they want shade, bathrooms, and easy water. West Orange Trail handles long-run base miles from Killarney Station toward Winter Garden, and Shingle Creek Trail gets the nod when someone says it is by far the best. Orlando Runners Club keeps the week honest with Monday miles at Winter Park Mellow Mushroom, Wednesday runs in College Park and Cady Way, and Sunday 6, 7, or 10 miles in Winter Park. Orlando Social Run Club brings a relaxed 5K from PIGZZA. Disney Wine & Dine Half Marathon Weekend and WALT DISNEY WORLD Marathon Weekend anchor the calendar.

Cycling: Locals ride Cady Way Trail and Lake Baldwin Loop for easy spins, then stretch the legs on West Orange Trail, South Lake Trails, Little Econ Greenway, and Cross Seminole Trail. Florida Freewheelers, Great Rides Orlando, and Winter Garden Wheel Works keep group rides steady. The local climbs hit 7 km with 355 m elevation and over 1,100 ft climbing. The short climbs go 2 km with 399 m elevation. The Horrible Hundred brings the anchor event, with 35, 70, or 100 miles in November.

Season: October, November, January, February, March, April, and May give runners and cyclists the cleanest training window. Summer brings high temperatures, heavy humidity, and frequent afternoon thunderstorms, so locals move intervals early and keep Z2 honest before the heat bites. The Heatwave Half Marathon still gives summer runners a target. Winter turns the whole metro into race and gran fondo mode, with mild temperatures that make long runs, club rides, and back-to-back weekends easier. North dirt and sand routes can get hard after a lot of rain, so locals lean more on paved trails and backroads.