Trail Running calendar near Oakland 2026-2027

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 in Lakeland Florida on Feb 28 invites runners to tackle a fast, well groomed 10k loop used for NCAA Division II regionals. Choose from 10k, 30k, 50k or a five person 50k relay for a lively community race day.

Join the family friendly Run for the Springs 5K through scenic Silver Springs State Park trails on Saturday Feb 28, 2026. Enjoy a kids area, refreshments, door prizes, age group medals and a Traveling Cup for the fastest team.

Run single loop trails along the Withlacoochee River and through serene forest at the Long Play Trail Run in Brooksville. Choose from a 33.3 mile race, a half marathon or a 6K and earn a collectible vinyl record finisher award.

Escape to the Juniper and Hopkins Prairies for a scenic out and back ultra in Ocala National Forest, with 50K and 30K options. Entry is free, the field is capped at 50, registration opens Dec 1, 2025, and carpooling is encouraged.

Join the Formosa Spiked Apple 5k at Formosa Winery in Kissimmee for a scenic, partly grassy course and tasty cider treats. Choose 5 km or 1.5 mile, get a cider donut and a finisher medal that doubles as a bottle opener while supporting Flor..

Celebrate St Patrick in Tampa on March 21, 2026 at the Time to Paddy 5k 10k and Lucky 13.1, featuring races from a kid's dash and mile to a half marathon. Enjoy festive shirts, finisher medals, chip timing and virtual options.

Explore the scenic trails of Silver Springs State Park on March 29, 2026 with a half marathon, 10K, 5K or virtual trail run. Enjoy a custom tech shirt and finisher medal as you race past springs, river and abundant wildlife.

Run the 30th Croom Fools Run on April 4 2026 in Withlacoochee State Forest near Brooksville Florida. Choose 16 mile 50K or 50 mile looped trail routes through pines creeks and cypress ponds with a capped field of 250 runners.

Run through scenic Colt Creek State Park in Lakeland on April 11, 2026 with 5K, 10K and half marathon options. Chip timed races include finisher medallions, swag and post race snacks for a fun day on the trails.

Join the fifth annual Turtle Trot at SunWest Park for 10K and 5K run or walk around scenic paved trails. Honor a fallen parks staff member and support Pasco County's adaptive programs while earning a finisher award.

The Funest 50k at Loyce Harpe Park invites runners to tackle twisty singletrack and rolling sand and dirt trails with 50k, 30k and 10k looped races. Limited fields and a $10 donation per entry to Polk County Parks and Recreation.

Run the Withlacoochee Trail Marathon on April 19 in Hernando on scenic forest trails with marathon, half and 10K options. All finishers earn an award and every entrant gets a cotton shirt and bib.

Run the Skunk Ape in Ocala FL on April 25 to 26 with 50 Mile or 100 Mile options on scenic trails. Expect sandy single track through pine woods and lakes, strong aid station support, with a buckle for 100 Mile runners.

Join Stomp Out Suicide on May 2, 2026 at Withlacoochee River Park for a scenic trail run or walk that raises awareness for suicide prevention. Choose 1 mile, 5K or 10K routes and enjoy a race shirt, snacks and a finisher award.

The Tick is a point to point trail ultramarathon of about 57 miles through the Ocala National Forest along the Florida National Scenic Trail. Crew support is required on this wild, scenic route.

Run the Turkey Creek 5K at Turkey Creek Sanctuary in Palm Bay on May 23, 2026 with in person or virtual options for runners and walkers. Enjoy race shirts, custom medals for the first 300 and post race refreshments.

Hit the trails on May 24 in Inverness FL for Sweat, Swat n Swear offering single loop 50K, 25K or 10 Miler courses through the scenic Citrus Tract at Holder Mine Campground. Expect aid stations, a finisher award and a lively post race picni..

Run the Florida Run LEFTOVER Trail Race on June 13, 2026 at Lake Louisa State Park in Clermont, featuring scenic 4 and 8 mile trail courses. Professionally timed with awards, a leftover medal, live music and post race food for a family frie..

Experience the low frills Independence Double in Winter Park on June 27 to 28 with lap based 5K to 50K on a flat, shaded paved trail. Hand timed and cupless, the relaxed event suits self supported runners looking for simple aid and communit..