Trail Running calendar near Greater Carrollwood 2026-2027

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 ultramarathon at Lake Louisa State Park in Clermont, FL offering 50K and 25K on a 16.2 mile loop with varied terrain, mostly singletrack, four aid stations, timing, medals, and free race media.

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 16.8 mile loop course preview and training run at Colt Creek State Park in Lakeland, FL. Unstaffed water stations provide water only, so participants should bring food and secure gear in vehicles. Primitive tent camping is availabl..

RunFluent Christmas in Lutz, Florida offers trail and timed events from a four mile loop to a new half marathon with awards and finisher woodals. Registration closes December 11 and refunds are not issued.

Candy Cane Course in Orlando on 12/13/2026 offers 5K, 10K, 15K, a 1 Mile, a Kids Dash and a virtual option. Entries normally include a designer shirt, custom bib and finisher medal, with youth pricing for ages 12 and under.

Central Florida Spartan Trifecta Weekend at Skipper Ranch in Sebring features obstacle races across farmland, marsh and mud. Distances include Sprint 5 km, Super 10 km, Beast 21 km and a kids race, with an obstacle workshop the day before.

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.

A looped event at Lake Wailes offering 4.17 mile, 6 hour, 12 hour and 12 hour relay options. Food is available at the Runners Village and all participants receive a long sleeve shirt.

Holiday-themed races at Gadsden Park in Tampa on December 27, 2026, with distances from a kids 50 m dash to 15K, plus a virtual option, chip-timing, shirts, medals, photos, and finish-line treats.

A looped trail event at Colt Creek State Park near Lakeland, FL, offering a 100-mile Western States qualifier and a 12.5-mile 100 Furlongs option with staffed aid stations and loop drop bag access.

A chip timed 5 km run and walk at Masaryk Winery in Masaryktown, Florida on January 16, 2027, with a helper registration option, race items including a t-shirt and wine glass, and results posted online by J3 Timing.

In-person and virtual races at Oscar Scherer State Park on January 23, 2027, featuring a mostly hard-packed 5K and a technical Scramble 10K with sugar-sand sections. Finisher medals, shirts while supplies last, chip timing and age-category..

A free, donation-supported 12-hour trail event at Whispering Pines City Park in Inverness, FL. Runners use a marked 5-mile loop on mixed trails, with an aid station and a finisher award for 10 miles or more.

A 5K and 10K trail run at Lake Manatee State Park featuring sandy paths, pine corridors, wildlife sightings, chip timing, finisher medal, and post-race refreshments. A lodging partner offers a promo code RUN for event dates.

Trail races at Bone Valley ATV Park include a 10K, 5K, and a 1 mile color run on hilly, uneven trails. Back to back challenge options require an 18 minute per mile pace and awards are given by age category.

Trail races on February 14, 2027 in Seminole State Forest at the Bear Pond Trail Head offer 5K, 12K and half marathon distances. The nonprofit event directs proceeds to forest improvements and registration fees may be tax deductible.

Experience a scenic trail race through the Carlton Reserve in Venice with distances ranging from 5k to 15k. Enjoy post race snacks and unique handmade wood awards in a festive community atmosphere.