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Trail Running Calendar near Kissimmee 2026-2027

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Explore the top trail runs near Kissimmee for 2026-2027! We've gathered 16 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

September 2026
Sep
27
Su

Bodies Race Company - Orlando

Trail Run 3 mi 6 mi 13 mi
A race day at Jay Blanchard Park on 09/27/2026 with distances from a 50 m kid's dash to a 13.1 mile half marathon, chip timing for main races, event shirts and medals, plus volunteer and virtual options.
October 2026
Oct
10-11
Sa - Su

Orlando Spartan Weekend

Obstacle Run 5 km 10 km
Orlando Spartan Weekend at Lake Nona features sprint and super obstacle races, kids events, a Hurricane Heat and an obstacle workshop across Oct 9 to 11, 2026.
Oct
10
Sa

We Care 5K

Trail Run 5 km
Lutheran Counseling Services holds the We Care 5K on October 10, 2026 in Longwood to raise funds and awareness for mental health. The event offers an in person 5K along parts of the Seminole Trail and a virtual 5K option.
Oct
25
Su

Clermont Clay 15K

Trail Run 5 km 15 km
Experience the famous clay trails of Clermont in this hilly off road event featuring timed 15K and 5K distances. Run along scenic 5 Mile Road and enjoy a professional racing environment with full course support and finisher medals.
Oct
31
Sa

Nightmare on the Clermont Trails 5K

Trail Run Walk 5 km
A Halloween 5K in Clermont with haunted spook zones, a costume contest, and a live DJ. A virtual 5K option includes shirt, bib, medal and domestic shipping.
November 2026
Nov
7
Sa

Bodies Race Company - Orlando

Trail Run 3 mi 6 mi 13 mi
Celebrate Thanksgiving with a series of themed races including a Half Marathon, 10k, and 5k in Orlando. Enjoy chip timed results, finisher medals, and family friendly distances like the Kids Dash and 1 Mile fun run.
Nov
26
Th

Turkey Day 5K Clermont

Trail Run 5 km
A Thanksgiving-themed 5K at Waterfront Park in Clermont, FL on November 26, 2026. The out and back course runs on the Upper Tampa Bay Trail and registration includes chip timing, a shirt, a finisher medal, awards, and photos.
Nov
28
Sa

Turkey Burn Ultra

Trail Run 25 km 50 km
A trail ultramarathon at Lake Louisa State Park with 50K and 25K options, varied singletrack terrain, four aid stations, and on-course media coverage.
December 2026
Dec
13
Su

Bodies Race Company - Orlando

Trail Run 3 mi 6 mi 7 mi
Candy Cane Course in Orlando on 12/13/2026 offers 5K, 10K, 15K, a 1 Mile, a Kids Dash and a virtual option. Entries normally include a designer shirt, custom bib and finisher medal, with youth pricing for ages 12 and under.
Dec
19
Sa

Sleigh It

Backyard Ultra 4 mi
A multi-format running event at Lake Wailes Park featuring 4.17 mile loops with 6 hour, 12 hour, single-loop and relay options plus aid stations and awards.
January 2027
Jan
30-31
Sa - Su

Forgotten Florida

Trail Run Walk 8 mi 15 mi 50 mi 100 mi
A multi-distance trail event in Christmas, Florida on January 30 and 31, 2027, running through Tosohatchee and nearby state forests with single track, varied terrain, wildlife viewing, course maps, aid station details, and crew and volunteer support.
February 2027
Feb
13
Sa

Lake Apopka Scenic Trail

Trail Run Walk 5 km 8 mi 13 mi 30 km
Trail races at Lake Apopka from 5K to 30K on packed lime rock and hard-packed Northshore trails, with support stations and awards; starts and finishes at Magnolia Park.
March 2027
Mar
14
Su

Formosa Spiked Apple 5K

Trail Run Walk 5 km
A chip timed 5K run/walk at Formosa Winery in Kissimmee on March 14, 2027. Registration includes a T-shirt, a medal that doubles as a bottle opener, a pour of cider and a homemade cider donut.
April 2027
Apr
10
Sa

Last Man Standing Orlando

Backyard Ultra 4 mi
A backyard ultra at Lake Louisa State Park on April 10, 2027 where runners complete a 4.167 mile loop each hour until they can no longer start a loop; shirts, medals, ribbon sliders, and multiple award categories are offered.
May 2027
May
8
Sa

Run for the Trees Jeannette Genius McKean Memorial 5K

Road Race Trail Run Walk 5 km
A point to point 5K in Winter Park with a final mile on a tree canopied dirt road, event swag, reusable-cup hydration options, and a tree sapling for in-person finishers.
June 2027
Jun
26-27
Sa - Su

Independence Double

Urban Trail 5 km 10 km ... 26 mi 50 km
Two-day running event on June 26 and June 27, 2027 at Cady Way Trail Head in Winter Park, FL. Distances range from 5K to 50K on flat, looped paved trails with a pavilion aid station and hand timing.
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