Land O' Lakes
Trail Running Calendar near Land O' Lakes 2026-2027
Explore the top trail runs near Land O' Lakes for 2026-2027! We've gathered 23 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
A Halloween-themed 5K, 1-Mile Fun Run and virtual 5K in Dunedin/Palm Harbor benefiting Club-214 Land & Sea and veteran support services.
Second annual Withlacoochee River 5K Run/Walk in Dade City on Oct 17 2026 with live 5K, 1 mile and virtual 5K plus medals, awards and charitable giving.
November 2026
PHSC hosts a flat 5K and a 1 Mile run/walk on November 1, 2026 at PHSC West Campus with awards, participant shirts, and post-race refreshments.
Obstacle course event on November 14, 2026 in Dade City FL with a 3+ mile BLITZ (15–20 obstacles) and a 5–7 mile race (25+ obstacles).
A self-guided, point-to-point urban endurance tour of about 100 miles from Ybor City through Tampa Bay beaches to a finish at Coffee Pot Park in St. Petersburg.
Trail and family runs at Sand Hill Scout Reservation in Brooksville, featuring a 5K, a costume 2.5K Turkey Trot, and a 0.8K Color Fun Run.
First annual Kilted 5K walk and run in Dunedin with a trail through Hammock Park; entry includes a T-shirt, medal, and admission to the Dunedin Celtic Festival.
Thanksgiving morning 5K on the paved Upper Tampa Bay Trail in Tampa with costumes encouraged, finisher medals, music, and family-friendly activities.
Third annual Salty Soul Splash Dash is a 5K fun run in Dunedin on 11/28/2026 along the Pinellas Trail with race timing, a shirt, and a cold beverage.
December 2026
January 2027
Trail runs at Croom Park near Brooksville, FL offering 50K, 20M and 10M on a 10 mile loop with aid stations about every 5 miles.
Timed 5k at Masaryk Winery in Masaryktown, FL, with on-site wines, a finisher medal that doubles as a wine stopper, and race timing by J3 Timing.
March 2027
Trail races on March 6, 2027 at Ridge Manor Trailhead near Brooksville, FL featuring 33 1/3 mile, half marathon and 6K courses through the Croom Tract.
April 2027
A 5K kilted trail run and walk in Dunedin with race shirt, medal, and festival admission included as part of the Highland Games.
Trail races on April 3, 2027 in Brooksville, FL: 50M, 50K and 16M run on a 16-mile loop through Withlacoochee State Forest with aid stations and packet pickup.
A naturist 5K run and 2K walk on April 11, 2027 at Lake Como Family Nudist Resort with resort access included and a background check requirement for guests.