Trail Running calendar near Osprey 2026-2027

A community 5K at Robinson Preserve in Bradenton on June 13, 2026, with a $35 registration fee. Participants receive a t-shirt, snacks and hotdogs, and awards are given to the top three men and women in each age group.

InHouse Ultra is a last one standing treadmill competition for 33 athletes held inside Run Unlimited and Twenty One Run. Competitors run five miles every hour and must complete each set to stay in the race.

Summer Sizzler in Tampa on 08/01/2026 features timed 5K 10K and 15K races, untimed 1 mile and kids dash, and a virtual option. The event includes chip timing, shirts and medals, free photos and finish line treats.

A self-supported six hour Fat Ass event at Walsingham Park in Seminole, FL on August 1, 2026. Runners use an approximately 3 mile paved out and back loop and self-record laps on clipboards for official results.

An ultramarathon in Pinellas County, Florida measured at just over 46 miles, running along the Pinellas Trail from St. Petersburg toward Tarpon Springs and returning toward Dunedin.

Tick Tock Ultra is a timed running event on September 19, 2026 offering 6 hour and 12 hour formats plus a 12 hour five person relay, organized by Ultra Ultras with registration via UltraSignup.

A timed lake-lap event at Lake Hollingsworth offering 12 hour, 6 hour and 12 hour team relay formats on 2.84 mile paved laps. The race has a hard cap of 200 entrants and supports the Pheel Good Foundation.

Choose a 5 km or a two loop 10 km course from HOB Brewing Company along the Pinellas Trail. Stroller and dog friendly with electronic timing, finisher medals, and a free draft beer for participants aged 21 and over.

A multi distance running event in Tampa with a half marathon, 10K, 5K, 1 mile, kids dash and virtual option. Features include chip timing, designer shirts and finisher medals, with youth pricing for ages 12 and under.

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 on October 17 2026 along the Pinellas Trail supporting Club-214 Land & Sea. Proceeds fund veteran services; participants receive finisher medals and costume prizes.

An 8K trail run through Weedon Island Preserve with mangroves, salt marsh and Tampa Bay views; race proceeds support the Friends of Weedon Island and include a technical shirt, timing and awards.

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.

A multi-discipline outdoor event in Arcadia, Florida on 11/07/2026 featuring a 5K trail run, a 15K mountain bike race, and a combined 20K Stampede Challenge, with awards, finisher hats, vendors, live music, and support for Eirene Ranch.

Family-focused mud run in Ave Maria with 1.5 to 2 miles of course and 10 to 16 obstacles, open to participants aged 5 and up; participant entries and a dog entry option have separate fees.

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.

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.