Longwood
Walking Events Calendar near Longwood 2026-2027
Monthly updates for Longwood
Get new running races (and updates) in your inbox every month.
Explore the top walking events near Longwood for 2026-2027! We've gathered 103 great walks in the area. Check out our detailed list below to find your next local walk.
December 2026
Walkers follow a 5K route along the back nine of the Grande Lakes golf course through resort grounds. Check in and packet pickup are on Valencia Lawn adjacent to the Spa; self parking is complimentary plus yoga and post event refreshments.
January 2027
Walkers can choose 100, 50, 15, or 8 MILE routes starting in Christmas, FL on wild scenic single track through Tosohatchee and Seminole Ranch with some mud, roots and aid stations.
Walkers can join the chip timed 5K (3.1 miles) across the Lake Brantley and Forest City campuses at 991 Sand Lake Road in Altamonte Springs. Course uses campus paths with community vendors and a virtual 5K option and shirts and medals for registr..
February 2027
Walkers follow an approximately 3 miles route through SeaWorld Orlando park pathways and the Sesame Street neighborhood and start behind the runners; free race day parking is included.
Walkers can join the 5K 3.1 Miles route at Camp Boggy Creek in Eustis, following camp trails through natural surroundings. The course offers a water station and a finish clock, with packet pickup on race day and free on site parking; no chip timi..
Walkers may cover the 5K course at Bill Frederick Park in Orlando on park terrain, with in person and virtual options alongside the running races.
Walkers use the hard packed limestone Lake Apopka Northshore trail at Magnolia Park for 3.1 Miles or a virtual 18.6 Miles walk; event is cupless so bring water.
Walkers can choose 5K (3.1 miles), 12K (7.14 miles) or Half Marathon (13.3 miles) routes from Bear Pond Trail Head through the scenic trails of Seminole State Forest.
March 2027
Walkers can take the 10 km or 2 mile routes from Central Park, Winter Park, on tree canopied roads with slight inclines and Chain of Lakes views; 15 min/mi pace required.
Walkers follow the 5K course along the back nine of the golf course at Grande Lakes, with check in at Valencia Courtyard adjacent to the Spa and complimentary parking.
Walkers can choose 10K or 5K on the flat out and back South Lake Trail along Lake Minneola, starting at Waterfront Park, Clermont; aid stations open four hours.
April 2027
Participants may choose in person or virtual 5K options, with the in person course starting at 2501 General Rees Ave in Orlando. The family friendly event is held alongside the fun run and raises funds for Paving the Way Foundation prevention edu..
Walkers follow an out and back on hard packed clay roads at Southern Hill Farms in Clermont FL, covering 5K (listed as 3.1 miles). The event includes a free pancake breakfast and a pint of u pick blueberries at the venue; virtual entries excl..
Walk the scenic 5K through downtown Orlando finishing at Lake Eola Park, with a Walker start on N. Eola Drive, purple bibs, team and virtual options.
May 2027