Trail Running calendar near Englewood 2025-2026

The 22nd Annual Dunedin OkotBEERfest 5K and 10K takes place at HOB Brewing Company in downtown Dunedin, Florida. Runners and walkers can choose OktoBEERfest 5K or 10K, with the 10K run as a two-loop course on the fully paved Pinellas Trail through downtown Dunedin. The event is dog- and family-frien..

Tick Tock Ultra is a Lakeland, Florida lake-lapping endurance event offering 12-hour and 6-hour races, plus a 12-hour relay for teams of 3–5. Runners complete 2.84-mile laps on a paved walkway around Lake Hollingsworth, aiming to log as many laps as possible before the finish. The atmosphere centers..

Trick or Trot 5K Trail Run, presented by Mazda of Port Charlotte, takes place at Ann & Chuck Dever Regional Park in Englewood, Florida. The event features a 5K trail run on a mostly dirt and gravel course, plus a 1-mile trail walk dubbed the Zoomers Trick or Trot. Participants are encouraged to wear..

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 scrub, with dirt and boardwalk sections and frequent views of..

The Tampa Bay 100 Mile Endurance Run is a third-year, point-to-point urban ultramarathon organized by Skunk Ape Events. The course begins in Ybor City, Tampa, winds through the city and across the bay to Safety Harbor, Dunedin, Clearwater, and Gulf Boulevard, finishing at Vinoy Park in St. Petersbur..

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 northbound out-and-back route. The 10K is two loops of the 5K course;..

Turkey Trails- Fort Myers, organized by Bodies Race Company, takes place at South County Regional Park in Punta Gorda, Florida. The Thanksgiving-themed event offers multiple distances—1 Mile, 5k, 10k—plus a Kids Dash, Volunteer-then-Run option, and a Virtual Race. Attendees can expect a family-frien..

Colt 45 Trail Run, staged by A1 Ultra Events, is held at Colt Creek State Park in Lakeland, Florida. Four distances are offered: Colt Double Malt (60 miles, four 14‑mile loops plus a bonus loop), Original Colt 45 (45 miles, three 14‑mile loops plus a 3‑mile starter loop), Colt Silver (45K, two 14‑mi..

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-run option. The course is designed around local parks with ma..

The Legacy Trail Ultra is a free 60-kilometer ultramarathon held in Sarasota, Florida. In its fourth year, the event follows an out-and-back course along the Legacy Trail, starting at Payne Park and heading south about 18.6 miles before returning to the start. There are no road closings and only lim..

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 County Sheriff, starting from near Citrus Park. The event in..

The 14th Annual FGCU XC Gobbler 5K is a community running event held at Florida Gulf Coast University’s Alico Arena in Fort Myers, Florida. The event features a 5K run/walk that loops around the scenic campus, a 1-mile run/walk, and a Tot Trot for children, all designed to support the FGCU Cross Cou..

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 atmosphere with local vendor booths, music, and community spirit.The..

The Caloosa Fest 5K is a trail running event held at Caloosahatchee Regional Park in Alva, Florida. Scheduled for December 6, 2025, it is part of a day-long festival that also features ultra races of 25K and 50K distances. The event offers a scenic trail course with a supportive atmosphere including..

The Caloosa Fest Ultra in Alva, Florida, at Caloosahatchee Regional Park, offers 50K and 25K ultramarathons along with a 5K trail race. The course features an 11.1-mile loop with varying terrain, rolling hills and technical sections, running the perimeter along Green, Black and Blue trails. Runners..

Candy Cane Course- Tampa, organized by Bodies Race Company, takes place in Tampa, Florida (venue to be announced) on December 13, 2025. It offers 1 mile, 5k, 12k, Kids Dash, and Virtual Race, plus a Volunteer option. The holiday-themed, family-friendly event features chip-timed 5k/12k with live resu..

The Peace River 100 Miler is an ultramarathon held at Mosaic Peace River Park in Bartow, Florida. The course features a challenging 10-mile loop combining equestrian trails, sandy paths, rolling grass, and limestone roads. Runners face a 36-hour cutoff to complete the 100-mile distance, with aid sta..

The Downtown Dunedin Holiday 5K, 10K, and 15K With Toy Drive is held at HOB Brewing Company in downtown Dunedin, Florida. It offers three distances: a 5K, a 10K (two 5K loops), and a 15K (three 5K loops), all on a fully paved course along the Pinellas Trail that starts and finishes at HOB. The event..

Bodies Race Company presents the Candy Cane Course in Punta Gorda, Florida, held at South County Regional Park-Baseball Field. The holiday-themed race offers 5k and 12k, plus family-friendly options including a 1-mile run and a Kids Dash, plus a Virtual Race. Participants can expect a designer shirt..

Long Haul 100 in Lakeland, Florida, is a premier 100-mile and 100-furlong trail race held at Colt Creek State Park. The course showcases Florida’s diverse, scenic landscape, with runners passing wildlife such as bald eagles, deer, alligators, otters, tortoises, and fox squirrels. The 100-mile option..