Trail Running calendar near Holiday 2026-2027

Join the 26th annual Scrub Jay Races at Oscar Scherer State Park in Osprey, FL on January 24, 2026, with a fast 5K, a technical 10K trail scramble, and virtual options. Enjoy scenic courses, finisher medals, and proceeds supporting Friends..

Run a scenic 5k through Masaryk Winery vineyards with chip timing and a festive wine themed finish. Receive a tee, shatterproof collapsible wine glass and a finisher medal that doubles as a wine stopper while supporting Nik's Wish.

RunFluent's Coo Wah Chobee returns as a single loop trail run at Carlton Preserve in Venice FL, featuring mixed single and dual track trails. Distances from 50k to Youth 5k, plus signature swag and Wicked Skin awards.

A community 5K at Legacy Park in Venice, FL on January 31, 2026, with two age-based categories, chip timing, and post-race activities. Hosted by Respect 1st Responders to raise funds for Disaster Relief Kits; field limited to 200 runners.

Celebrate the new year with Westly's 9th Annual 5K in Oakland, Florida. Run or walk the in person West Orange Trail event or join virtually anytime in January for a free, family friendly 5K with post race festivities and live music.

Celebrate Mardi Gras at Celery Fields with 5k, 10k and canicross races for runners and their dogs. Expect shirts, post race snacks, live music, vendors and age group awards plus a guided warm up.

Race under the stars at AdventHealth Nighthawk Trail Run in Colt Creek State Park with 5K, 10K and a 15K Challenge. Rugged unpaved loops, headlamp required for the 5K, finisher medals and a race shirt promise a memorable night on the trails..

Join the Gopherdillo Trail Run at Lake Manatee State Park on Feb 7, 2026 for scenic 5K and 10K non loop courses over sand, grass and paved roads. Expect wildlife sightings, a performance shirt option, and a finisher medal.

Join The Hunt for Sasquatch at Bone Valley ATV Park on February 7, 2026 for a fun trail challenge over varied terrain and small hills. Choose from 10K, 5K, 1 Mile or multi race options, with shirts, swag and awards.

A trail event at Green Swamp West Tract near Dade City offering 60K, 30K and a 30K ruck on varied Florida terrain with aid stations every 3 to 5 miles, finishers hats, and a local pet food drive.

Sasquatch invites runners to Carlton Preserve in Venice Florida for 15k, 10k, 5k and a virtual race on Feb 15 2026. Expect race shirts, snacks, live music, vendor booths and a guided group stretch for all abilities.

Join the inaugural Longleaf Blaze Trail Run at Disney Wilderness Preserve with 5K, 10K or Double Down options. Family friendly with kids activities, finisher medals and hats; bring your own water bottle and enjoy scenic trails.

Celebrate Mardi Gras on the flat, paved Pinellas Trail with 5K, 10K or 15K options hosted at HOB Brewing Company in Dunedin. Limited to 200 runners, all finishers get a medal and 21 plus registrants enjoy a complimentary beer.

Join the Painted Horse Urban Ultra in Ocala on Feb 21 for a self supported, navigation heavy adventure. Choose 55k or 25k routes that visit dozens of painted horse sculptures, and it is not a race but a sightseeing scavenger hunt.

Explore Lakeland on a 30k urban adventure visiting painted swans from the Swansation art trail while navigating with a race book. This low key, self supported run from the Where's the Finish? Podcast mixes city charm and relaxed challenge.

All Day at Holloway offers a well groomed cross country loop of trail and road at Holloway Park in Lakeland on Feb 28, 2026. Choose 10k, 30k, 50k or a five person 50k relay.

Run scenic single loop trails along the Withlacoochee River in the Croom Tract with options from 6K to the challenging 33.3 mile distance. Enjoy aid stations, a post race picnic and a quirky vinyl record finisher award.

Run the 30th Croom Fools Run in Withlacoochee State Forest near Brooksville, FL, with 16 mile, 50K and 50 mile options on a scenic 16 mile loop. Limited field and a laid back post race picnic make for a classic trail day.

Run through scenic Colt Creek State Park in Lakeland FL on April 11, 2026 with 5K, 10K, and half marathon distances. Trails, chip timing, a finisher medallion and post race snacks make this a lively spring event for runners and clubs.

Join the Turtle Trot 10K and 5K at SunWest Park on April 11 for scenic paved loops around old salt mines, perfect for runners and walkers. All finishers get awards and proceeds benefit Pasco Parks adaptive programs in memory of a staffer.