Trail Running calendar near Holiday 2025-2026

Run the historic John Holmes Trail Run on October 4, 2025 in Brooksville, FL, featuring the Southeast's oldest 50K plus 16 mile and 9 mile options. Enjoy singletrack through pines, creek bottoms and cypress ponds with shirts, awards and pos..

Test your trail legs on a rugged 50K along the Florida National Scenic Trail West Corridor in Ocala on October 18, 2025, finishing at Baseline Road Trailhead. Enjoy aid stations and a drop bag zone for unsupported runners.

Location: Palm Harbor, Florida, on the Pinellas Trail with Start/Finish at De Bine Brewing Company (993 Florida Ave). Distances: a 5K (3.1 miles) and a 1-mile Fun Run/Walk. Atmosphere: inaugural Halloween-themed event encouraging participan..

Nightmare on the Clermont Trails 5K takes place in Clermont, Florida, on October 25, 2025. The event offers a 5K Run/Walk on the scenic Clermont Trails and a Virtual 5K option for remote participants. As dusk falls, the course is transforme..

The Gopher Weedon Trail Run is an 8K trail race held at Weedon Island Preserve in northeast St. Petersburg, Florida (1800 Weedon Dr NE, 33702). The course covers about 4.9 miles of natural trails through mangroves, salt marsh and Florida sc..

The Greenway Trick 'R Trot is a Halloween-themed trail race held at the Pruitt Trailhead in Dunnellon, Florida. Scheduled for October 25, 2025, the event offers multiple race options including 5K and 10K runs and rucks, as well as combined..

Run with the Bobcats 5K or 1 Mile is a cross-country event hosted by Pasco-Hernando State College in New Port Richey, Florida, at 10230 Ridge Rd. The day offers a 5K Run/Walk and a 1 Mile Fun Run/Walk along a flat, fast course, including a..

The Florida Run stages the Lake Louisa State Park Trail Run in Clermont, Florida, offering 5K, 10K, and Half-Marathon distances. Runners navigate a scenic course through pine forests, lakeshores, and open meadows with varied terrain and mod..

Run 100 miles across Tampa Bay on a point to point urban ultra starting in Ybor City and finishing in Vinoy Park. Enjoy murals, waterfront views, beaches and city sights on a mostly flat, scenic endurance tour on Nov 8, 2025.

The Dunedin Veterans Day 5K, 10K and Kids Dash Runs take place in downtown Dunedin, FL. The course starts and finishes near the VFW at the Dunedin Hale Center, 330 Douglas Avenue, and runners traverse the paved Pinellas Trail on a northboun..

Landbridge Trail 5k is a well-marked, 5-kilometer loop on the Florida Trail in Ocala, Florida. The course climbs to the top of the famed Landbridge in the Marjorie Harris Carr Cross Florida Greenway, following Blue and Orange blazed trails...

Run Colt Creek trails on November 22, 2025 with options from a single 14 mile loop to a 60 mile ultrarun. Enjoy pine flatwoods and wildlife, then celebrate with a handcrafted finisher award and post race picnic.

Turkey Trails - Tampa, organized by Bodies Race Company, is a Thanksgiving-themed, family-friendly running event in Tampa, Florida (location listed as TBD, 33611). It offers 1 Mile, 5k, 10k, Kids Dash, a Virtual Race, and a Volunteer-then-r..

Event details The Legacy Trail Ultra is a free, 60K ultramarathon in Sarasota, FL, organized by the Manasota Track Club. It is the fourth annual running of the event and uses the Legacy Trail as its course. The route is an out-and-back that..

Turkey Day 5K Tampa Bay is a Thanksgiving-themed 5K run/walk held along the Upper Tampa Bay Trail in Tampa, Florida (near Citrus Park). The scenic, nice-down-and-back course follows the trail with a street crossing assisted by Hillsborough..

Turkey Day 5K Clermont is a Thanksgiving-themed 5K held at Waterfront Park in Clermont, Florida. The course is described as a nice down-and-back on the Waterfront Park paved trail, starting near the shelter past the splash pad and offering..

Take on Florida 48 at Ocala's Shangri La Campground: run 4 miles every 4 hours for 48 hours, enjoy three nights of camping and meals, support on a mostly flat out and back course, and earn a finisher patch. Limited to 100 runners.

The Trail Hog Half Marathon is a trail running event held at Carlton Preserve in Venice, Florida. It features three race distances: a half marathon, a 10k, and a 5k, catering to a wide range of runners. Participants enjoy a festive atmosphe..

Turkey Trails- Orlando, run by Bodies Race Company, unfolds at Waterfront Park in Clermont, Florida. This Thanksgiving-themed event offers 1 mile (untimed), 5k, 10k (two laps), a Kids Dash, plus Volunteer-then-Run and Virtual options. It fe..

Run Thanksgiving weekend at Lake Louisa Park in Clermont Florida with 50K and 25K trail options across wooded singletrack and sandy hills. Tackle a scenic 17 mile loop with four aid stations, pro timing and a finisher medal.