Trail Running calendar near Greater Carrollwood 2026-2027

A multi-distance running event at Jay Blanchard Park on September 27, 2026 offering a half marathon, 10K, 5K, 1 mile, kids dash, volunteer option and a virtual race, with bibs, shirts and finisher medals provided for most entries.

The John Holmes Trail Run takes place at Croom Park and Withlacoochee State Forest on October 3, 2026, offering 50K, 16 mile and 9 mile options. The field is limited to 250 runners and this is the event's 34th running.

A multi-format Spartan Race weekend at Lake Nona in Orlando with Sprint and Super obstacle races, a kids course, an obstacle workshop and a 4 hour Hurricane Heat. Team registration is available, and qualifying service member discounts apply..

A Halloween themed trail event in Englewood offering a 5K and a 1 mile walk at Ann & Chuck Dever Regional Park. Shirts, bibs, 5K finisher medals, costume awards and proceeds benefit the Zoomers Scholarship Fund.

A Halloween themed 5K and 1 Mile Fun Run/Walk on the Pinellas Trail in Palm Harbor benefiting Club-214 Land & Sea, with finisher medals, costume prizes, age group awards, and proceeds supporting veterans and their families.

A dog-friendly, off-road 3.1 mile trail event at Rock Springs Run State Reserve offering timed results, participant and dog finisher medals, event shirts while supplies last, included park admission for one guest, and on-site packet pickup.

A Halloween-themed trail event at Pruitt Trailhead in Dunnellon offering 5K and 10K runs and rucks plus a combined 5K+10K challenge. Ruck weigh-in standards apply and headlamps are required for the longer courses.

An 8K trail race through Weedon Island Preserve on October 24, 2026, featuring natural trails, boardwalks, views of Tampa Bay and professionally timed results; proceeds support Friends of Weedon Island.

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 near Lake Wales, FL where runners complete repeating 4.167 mile loops each hour until one runner remains. Crews and personal aid are allowed between loops and total distance is recorded for all participants.

A chip-timed trail run at Lake Louisa State Park with 5K, 10K and half-marathon options, aid stations roughly every two miles, on-course restrooms, post-race food and awards for individual and team categories.

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.

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 Blitz of 3+ miles with 15 to 20 obstacles and a main course of 5 to 7 miles with 25+ obstacles; parking is $20 and spectator passes start at $25.

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 100 mile urban endurance run through Tampa Bay from Ybor City to St Petersburg, passing Safety Harbor, Dunedin, Clearwater and Gulfport. Five staffed aid stations, supplies caches, drop bags, and mandatory navigation and sa..

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 community running day at Sand Hill Scout Reservation on November 21, 2026, featuring a 5 km trail run, a 2.5 km turkey trot with costumes encouraged, and a 0.8 km color run. Proceeds support local Scouting programs.