256 Upcoming 5K Races Near Winter Garden, FL

Mon, Jan 18, 20271 race

Chasing the Dream 5K -MLK Day Celebration

Orlando, FL

Sat, Jan 23, 20274 races

DeBary 50K, Marathon, Half, 10K & 5K – MileBuilt Gemini Springs 2-Day Challenge

DeBary, FL

2nd Annual UYA 5k Run It Back

Sanford, FL

Viking 5K & 10K at Plant City, FL (04)

Plant City, FL

Purple Pride 5k

Orlando, FL

Sat, Jan 30, 20279 races

Lake Mary's 10th Annual Run with a Hero 5K and Kids Run Sponsored by Orlando Health

Lake Mary, FL

Patriot Pride 5k

Altamonte Springs, FL

Wild Florida 5K

Orlando, FL

Orlando Magic 5K & Kids' Run Presented by AdventHealth

Orlando, FL

Time Travel Half-Marathon/5K/10K - Orlando

Orlando, FL

Ugly Pajama 5K Run - Clermont

Clermont, FL

ME STRONG 5K

DeLand, FL

Medal Madness 5K, 10K, & 13.1M, Deland, FL (05)

Deland, FL

Fri, Feb 5, 20272 races

Rotary Twilight 5k

Lakeland , FL

Twilight 5k

Lakeland, FL

Sat, Feb 6, 20277 races

Pirate 5K, 10K, & 13.1M at DeBary, FL (06)

DeBary, FL

Camp Boggy Creek 5K Fun Run and Gravel Ride

Eustis, FL

Angie Sharon Memorial 5K Heart Walk/Run

Edgewater, FL

Cherrylake Farm Races presented by Orlando Health

Groveland, FL

6th Annual Run for the Cherubs 5K & Walk benefiting Orlando Health Winnie Palmer Hospital for Women & Babies

Saint Cloud, FL

The Hunt for Sasquatch

Mulberry, FL

6th Annual School Spirit Run & Kids Run IGNITED By Addition Financial

Orlando, FL

Sun, Feb 7, 20271 race

AdventHealth Nighthawk Trail Run - Night Owl 5K and Coyote 10K

Lakeland, FL

Sat, Feb 13, 20276 races

AdventHealth Lake Apopka Scenic Trail 30K Run, 8 Miler & 5K

Apopka, FL

SDC 2027 (Strawberry Distance Challenge)

Plant City, FL

AHS Booster Club Cupid's 5K - Run With Your Heart

Titusville, FL

Medal Madness 5K, 10K, & 13.1M at Deland, FL (07)

Deland, FL

Cold Front - Orlando

Orlando, FL

Run for Resilience 5K

Orlando, FL

Sun, Feb 14, 20274 races

Tracked Chair Adventures -- Run for the Woods

Sorrento, FL

Love The Run You're With 5k

Lakeland, FL

Dream Finders Homes For the Love of Chocolate 5K

Clermont, FL

Bigfoot Challenge 5k/8k Presidents’ Day

Clermont, FL

Thu, Feb 18, 20271 race

Florida Five (Five Days, Five Different Locations, Five Distances to choose from)

Winter Park, Apopka, Winter Garden, Union Park & Orlando, FL

Sat, Feb 20, 20275 races

AdventHealth Howey-in-the-Hills 5K, 10K & Half Marathon presented by LiveTrends Design Group

Howey in the Hills, FL

Boone Brave Run

Orlando, FL

Husky Hearts 5K

Lake Helen, FL

Lakewood Center's Outrun Stigma 5k

Oviedo, FL

Winter Park 50K, Marathon, Half, 10K & 5K – MileBuilt Cady Way Bridge 2-Day Challenge

Winter Park, FL

Sun, Feb 21, 20271 race

SUPERHERO 5K- Compassion in Action

Orlando, FL

Fri, Feb 26, 20271 race

TECH CORPS Charity Group Registration (Princess Half Marathon Weekend 2027)

Kissimmee, FL

Sat, Feb 27, 20275 races

Squirrel 5K & 10K at Plant City, FL (09)

Plant City, FL

Squirrel 5K, 10K, & 13.1M at Deltona, FL (09)

Deltona, FL

Inua 5k

Orlando, FL

Running with the Herd 5k

The Villages, FL