Trail Running calendar near Holiday 2026-2027

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.

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.

A BACKYARD Ultra in Lake Wales, FL where runners repeat a 4.167 mile loop each hour until one runner completes a final loop alone. Aid is allowed between loops but not while on course.

Trail races at Lake Louisa State Park on November 7, 2026 include 5K, 10K and a Half Marathon over natural trails. The event features chip timing, aid stations, on-course restrooms and finisher medallions.

A Veterans Day running event in Dunedin offering a 5K, a two-loop 10K and a kids Honor Dash on the paved, stroller friendly Pinellas Trail with American themed finisher medals and timed results.

Celebrate Thanksgiving with this family friendly event in Tampa featuring distances from a Kids Dash to a Half Marathon. Enjoy chip timed results, finisher medals, and festive treats at the finish line.

Savage Race Florida Fall in Dade City on November 14, 2026 offers a 3+ mile BLITZ with 15 to 20 obstacles and a 5 to 7 mile main race with 25 or more obstacles. Entry fees rise by date and parking is $20.

The 6th Annual Veterans Run in Tampa returns with in-person and virtual races along the Courtney Campbell Causeway, offering 5K, 10K, half marathon, and a 15.5 mile course with certified timing and aid stations.

A point-to-point urban endurance tour from Ybor City to St. Petersburg covering about 100 mile of Tampa Bay sights, beaches and waterfronts. The mostly flat route includes five aid stations, supplies caches and specific pacing and mandatory..

Experience the natural beauty of Lakeland at Colt Creek State Park for a trail event featuring distances from 14 miles to a 60 mile ultra. Enjoy a loop based course with handcrafted medals and a post race picnic.

A set of runs on November 21, 2026 in Brooksville, Florida features a 5K trail run, a 2.5K Turkey Trot with costumes encouraged, and a short Color Fun Run with colored powder. Proceeds support Scouting programs.

Turkey Day 5K Clermont is a Thanksgiving tradition themed 5K at Waterfront Park in Clermont, FL on November 26, 2026. The out and back course uses the Upper Tampa Bay Trail and entries include chip timing, a finisher medal and a shirt.

A Thanksgiving 5K on the Upper Tampa Bay Trail in Tampa, FL on November 26, 2026. The chipped timed 5K includes a finisher medal, a soft short sleeve shirt, age group awards, free photos, and holiday-themed elements.

Experience the natural beauty of Carlton Reserve at this Florida trail event. Runners can choose between three distances and enjoy a pre race stretch session with recovery snacks and awards for various age groups.

A trail ultra at Lake Louisa State Park offering 50K and 25K options across 75% singletrack with varied terrain, four aid stations, professional timing and media, and awards across overall, masters, and age categories.

Trail races at Alafia River State Park on December 4-5, 2026 offer individual options: a 5.3 mile Red Loop, a timed 6 hour ultra, and a 24 hour ultra. The village includes camping, bonfires, music, food trucks, and finisher items.

A marked one-loop 16.8 mile course preview at Colt Creek State Park in Lakeland, FL with unstaffed water-only stations and primitive tent camping available; park entry fee applies and registration closes Dec 3.

RunFluent Christmas in Lutz, FL on December 12, 2026 offers multiple trail distances including a new 13.1 half marathon on a 4.45 mile course, finisher woodals, podium and age-group awards, and a no-refund policy with eligible deferrals.

A holiday run in downtown Dunedin on December 19, 2026 featuring 5K 10K and 15K routes on the Pinellas Trail with electronic timing finisher medals shirts and a post race beer option for those 21 and over.

Sleigh It is a loop based event at Lake Wailes Park in Lake Wales Florida offering 4.17 mile, six hour, and twelve hour options plus a twelve hour relay. The course uses grass and asphalt and has aid stations at each turnaround.