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Walking Events Calendar near Casselberry 2026-2027

Monthly updates for Casselberry

Get new running races (and updates) in your inbox every month.

Explore the top walking events near Casselberry for 2026-2027! We've gathered 100 great walks in the area. Check out our detailed list below to find your next local walk.

October 2026
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.
Walkers start at First United Methodist Church in Oviedo and follow the Cross Seminole Trail on an out and back route of 3.1 Miles or 6.2 Miles. A kids course of 1 Miles runs along a canopied road.
Walkers can join the 5K starting and ending at the Historic Civic Center in Longwood's historic district. The family friendly Halloween themed route follows streets through the historic district and includes a free kids dash.
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 do 3.1 Miles around Lake Mineola, starting and finishing on the grassy area at 330 Third St., Clermont; strollers start at back and dogs not allowed.
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..
5K walk starts and finishes on Park Avenue in Winter Park along a scenic course down Interlachen Avenue with homes, greenery and views of Lake Maitland. Walkers must maintain a 15 minute per mile pace.
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..
Walkers can choose 5K, 10K, or 13.1 Miles routes starting at 2100 Fatio Rd in Deland FL alongside the running races. Water is limited to the end of laps and the finish, so walkers should plan for weather, carry needed supplies, and check..
Walkers cover 3.1 Miles from Cadwell Park through scenic Umatilla on the USATF certified course, alongside the running race on marked roads.
A community 5K walk around Lake Baldwin from Harbor Park in Orlando, with packet pick up available at 150 W. Michigan Street.
Walkers can complete the 5K course at Blue Jacket Park in Orlando alongside runners, with fundraising, vendors, family friendly activities, and event day check in.
The event offers a 3.1 Miles walking route starting and finishing at Blue Spring State Park along the scenic, flat Spring to Spring Trail adjacent to the park. Park admission is included with registration and packet pick up is available before an..
Walkers follow a 5K waterfront route along Lake Minneola, starting at the Waterfront near 100 3rd St., Clermont. The community event welcomes walkers alongside runners and raises funds for River Clermont Food Distribution.
Walkers can choose 5K, 10K, or 13.1 Miles starting at 37 Dirksen Drive in DeBary FL. The course is local and clear but water is limited to lap ends and the finish, so walkers should plan for weather and bring supplies.
Walkers can take the 1.5 Miles course around Formosa Winery, passing vineyard and fruit orchards and finishing near the tasting house. They select their start time during registration and the walk takes place alongside the 5k.
Walkers can complete the chip timed 3.1 Miles course starting at 1700 Oviedo Mall Boulevard in Oviedo FL alongside the running races. The event includes chip timing and a finisher medal for participants.
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