Winter Garden
Walking Events Calendar near Winter Garden 2026-2027
Monthly updates for Winter Garden
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Explore the top walking events near Winter Garden for 2026-2027! We've gathered 68 great walks in the area. Check out our detailed list below to find your next local walk.
October 2026
Walkers can choose 5K, 10K, or 13.1 Miles routes starting at 37 Dirksen Drive in DeBary FL on a clear, marked local course. Staffing is minimal, EMS is not on site, and water is provided only at the finish and at the end of each lap.
Walkers complete a 5K course in Fort Mellon Park at 600 E 1st St, Sanford, FL, as part of a breast cancer awareness event alongside the running races. The event emphasizes solidarity with survivors and community support.
Walk the 5K course at Harbor Park, 4990 New Broad St, Orlando FL. Walkers receive finish line chocolate and event perks including a custom t shirt and a limited edition medal, with family friendly activities and a kids dash nearby.
Walkers follow a two lap 3.1 mile course (5K) through the campus of the Orange County Convention Center in Orlando. The event includes a t shirt, finisher medal, race bag and light breakfast, with walking offered alongside the running race.
Walkers can join Run/Walk events on the South Lake Trail at Waterfront Park in Clermont, including a 9.3 Miles 15K and a 3.1 Miles 5K. Both are out and back courses on the South Lake Trail alongside the festival multisport races.
Walkers can choose a 1 Mile Tribute Walk or walk the in person 3.1 Miles 5K at Oviedo Mall. Tribute walk registration includes a dri fit shirt and bib; 5K walkers get a dri fit shirt, chip timed bib and finisher medal.
From the St. Stephen Catholic Church field in Winter Springs this walk offers a 2.5 Miles route across church grounds and adjacent pumpkin patch. Registration is free, suggested donation $25; check in offers refreshments and raffle.
Walkers follow the 5K trail route starting at 938 Victory Way in Clermont, FL, on wooded trails with spooky themed spook zones as darkness falls. The walk runs alongside the running race and includes haunted zones and a costume contest.
November 2026
Walkers can follow the measured 3.1 Miles course starting at 1061 S Sun Dr, Lake Mary on a USATF certified route near the shopping plaza. Packet pickup is available at Front Running Sports, and registration plus a virtual 5k option are offered al..
Walk the 3.1 Miles course from Newton Park, 1 Surprise Drive, through Downtown Winter Garden, its historic neighborhoods and along Lake Apopka. Donut zones at miles 1, 2 and 3 provide on-course snacks that reduce finish time when eaten alongside th..
Walkers can choose 5K, 10K, or 13.1 Miles on a clear local course starting at 37 Dirksen Drive in DeBary FL. Course is staffed but water is limited to lap ends and the finish and EMS is not on site so plan accordingly.
Walkers can take part in the Race for Champions Orlando 5K at RFI Orlando, 3251 Margaritaville Blvd, Kissimmee, FL 34747, on November 7. Day of registration is available and packet pickup details are TBD, with the event held alongside the running..
Walkers can follow the 5K route starting and finishing on Park Avenue, a scenic course down Interlachen Avenue to Alabama Drive with views of Lake Maitland. Walkers are welcome alongside runners and must maintain about a 15 minute per mile pace o..
Walkers can choose a 3.1 Miles course or a 1 Miles youth route starting on the RLC campus at 31333 Round Lake Rd in Mount Dora. The course follows Round Lake Road which will be closed and includes sand dirt and grass on the cross country loop..
Walkers can take part in the 3.1 Miles course starting at 205 Windermere Road, Winter Garden FL, alongside the event running races. The event benefits The Gift of Swimming and its mission to expand drowning prevention resources and access to swim..