Upcoming Races in Winter Garden, FL 2026-2027

Ole Ole 5K - St. Cloud

St. Cloud, FL

Saturday, May 23rd, 2026

Featured

5K

View details for race Ole Ole 5K - St. Cloud

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Luau 5K, 10K, & 13.1 at Green Springs Park, Del...

Deltona, FL

Saturday, May 23rd, 2026

5K

10K

Half

View details for race Luau 5K, 10K, & 13.1 at Green Springs Park, Deltona, FL (21M60)

Memorial Day 5K/10K/15K - Lakeland

Lakeland, FL

Saturday, May 23rd, 2026

5K

10K

15K

View details for race Memorial Day 5K/10K/15K - Lakeland

Run for Their Lives 5k

Lakeland, FL

Saturday, May 23rd, 2026

5K

Trail

View details for race Run for Their Lives 5k

Remember & Honor - Memorial Day 5k & Master Yog...

Orlando, FL

Saturday, May 23rd, 2026

5K

View details for race Remember & Honor - Memorial Day 5k & Master Yoga Class- Restorative Yoga

Run the Course 5k

Howey In The Hills, FL

Saturday, May 23rd, 2026

5K

View details for race Run the Course 5k

*Spring Lake Memorial Classic* 2Mile / 5K / 10K

Brooksville, FL

Saturday, May 23rd, 2026

5K

10K

View details for race *Spring Lake Memorial Classic* 2Mile / 5K / 10K

Hometown Half Marathon & 5k/10k - Orlando

Orlando, FL

Saturday, May 23rd, 2026

1 Mile

5K

10K

View details for race Hometown Half Marathon & 5k/10k - Orlando

Rise & Remember

Orlando, FL

Monday, May 25th, 2026

5K

View details for race Rise & Remember

Medal Madness 5K, 10K, & Half Marathon at Lake ...

Deland, FL

Saturday, May 30th, 2026

5K

10K

Half

View details for race Medal Madness 5K, 10K, & Half Marathon at Lake Beresford Park, Deland, FL (22) 50

Doughnut Day 5K

Lake Mary, FL

Saturday, May 30th, 2026

5K

View details for race Doughnut Day 5K

Dr. Myron L. Rolle Pediatric Gun Safety 5k Walk...

Orlando, FL

Saturday, May 30th, 2026

5K

View details for race Dr. Myron L. Rolle Pediatric Gun Safety 5k Walk/Run

The Big Run Presented by Brooks

Orlando, FL

Wednesday, June 3rd, 2026

5K

Fast

View details for race The Big Run Presented by Brooks

The Big Run 5k Presented by Brooks

Plant City, FL

Wednesday, June 3rd, 2026

5K

View details for race The Big Run 5k Presented by Brooks

Treat Trot-Orlando

Minneola, FL

Saturday, June 6th, 2026

5K

10K

15K

View details for race Treat Trot-Orlando

Medal Madness 5K, 10K, & 13.1M at Columbus, GA ...

Columbus, FL

Saturday, June 6th, 2026

5K

10K

Half

View details for race Medal Madness 5K, 10K, & 13.1M at Columbus, GA (23)

Treat Trot-Orlando

Orlando, FL

Saturday, June 6th, 2026

5K

10K

15K

View details for race Treat Trot-Orlando

Medal Madness 5K, 10K, & Half Marathon at Gemin...

DeBary, FL

Saturday, June 6th, 2026

5K

10K

Half

View details for race Medal Madness 5K, 10K, & Half Marathon at Gemini Springs Park, DeBary, FL (23) 80

THE BIG RUN 2025 Fleet Feet The Villages, FL - ...

The Villages, FL

Saturday, June 6th, 2026

5K

View details for race THE BIG RUN 2025 Fleet Feet The Villages, FL - Global Running Day Celebration

The Florida Run LEFTOVER Trail Race

Clermont, FL

Saturday, June 13th, 2026

Trail

View details for race The Florida Run LEFTOVER Trail Race

Medal Madness 5K, 10K, & 13.1 at Lake Beresford...

Deland, FL

Saturday, June 13th, 2026

5K

10K

Half

View details for race Medal Madness 5K, 10K, & 13.1 at Lake Beresford Park, Deland, FL (24S40)

The Phrozen Jewel Run 5/10K

Orlando, FL

Saturday, June 13th, 2026

5K

10K

View details for race The Phrozen Jewel Run 5/10K

31st Summer Sunrise Watermelon Series | Lakelan...

Lakeland, FL

Saturday, June 13th, 2026

5K

View details for race 31st Summer Sunrise Watermelon Series | Lakeland, FL

Medal Madness 5K & 10K at Orlando, FL (24)

Orlando, FL

Saturday, June 13th, 2026

5K

10K

View details for race Medal Madness 5K & 10K at Orlando, FL (24)

AdventHealth Cool Sommer Mornings Triathlon-Dua...

Clermont, FL

Sunday, June 14th, 2026

5K

Ultra

Trail

View details for race AdventHealth Cool Sommer Mornings Triathlon-Duathlon-5K Series #1

Run with the Pack 5k

Orange City, FL

Sunday, June 14th, 2026

5K

View details for race Run with the Pack 5k

Lake Mary Summer Solstice 5K

Lake Mary, FL

Sunday, June 14th, 2026

5K

Trail

View details for race Lake Mary Summer Solstice 5K

Medal Madness 5K, 10K, & Half Marathon at Gemin...

DeBary, FL

Saturday, June 20th, 2026

5K

10K

Half

View details for race Medal Madness 5K, 10K, & Half Marathon at Gemini Springs Park, DeBary, FL (25) 80

Independence Double

Winter Park, FL

Saturday, June 27th, 2026

5K

10K

Half

View details for race Independence Double

Medal Madness 5K, 10K, & 13.1M at Deltona, FL (26)

Deltona, FL

Saturday, June 27th, 2026

5K

10K

Half

View details for race Medal Madness 5K, 10K, & 13.1M at Deltona, FL (26)

Red, White & Brew 5k

LAKELAND, FL

Saturday, July 4th, 2026

5K

View details for race Red, White & Brew 5k

AdventHealth Clermont Freedom 5K presented by L...

Clermont, FL

Saturday, July 4th, 2026

5K

Trail

View details for race AdventHealth Clermont Freedom 5K presented by Live Trends Design Group

Run, White and Blue 5k and Yoga Master Class

Orlando, FL

Saturday, July 4th, 2026

5K

View details for race Run, White and Blue 5k and Yoga Master Class

AdventHealth July 4th Watermelon 5K

Winter Park, FL

Saturday, July 4th, 2026

5K

View details for race AdventHealth July 4th Watermelon 5K

Four on the 4th

Orlando, FL

Saturday, July 4th, 2026

View details for race Four on the 4th

Eagle 5K, 10K, & 13.1 at Lake Beresford Park, D...

Deland, FL

Saturday, July 11th, 2026

5K

10K

Half

View details for race Eagle 5K, 10K, & 13.1 at Lake Beresford Park, Deland, FL (28S40)

$AdventHealth Cool Sommer Mornings Triathlon\Duathlon\5K Series #2 logo$

AdventHealth Cool Sommer Mornings Triathlon\Dua...

Clermont, FL

Sunday, July 12th, 2026

5K

Ultra

Trail

View details for race AdventHealth Cool Sommer Mornings Triathlon\Duathlon\5K Series #2

Heatwave Half Marathon - Orlando

Orlando, FL

Saturday, July 18th, 2026

1 Mile

5K

10K

View details for race Heatwave Half Marathon - Orlando

Eagle 5K, 10K, & 13.1M at DeBary, FL (29)

DeBary, FL

Saturday, July 18th, 2026

5K

10K

Half

View details for race Eagle 5K, 10K, & 13.1M at DeBary, FL (29)

Eagle 5K, 10K, & 13.1 at Green Springs Park, De...

Deltona, FL

Saturday, July 25th, 2026

5K

10K

Half

View details for race Eagle 5K, 10K, & 13.1 at Green Springs Park, Deltona, FL (30M60)

Ninja 5K, 10K, & 13.1M at DeBary, FL (31)

DeBary, FL

Saturday, August 1st, 2026

5K

10K

Half

View details for race Ninja 5K, 10K, & 13.1M at DeBary, FL (31)

Summer Sizzler- Orlando

Orlando, FL

Sunday, August 2nd, 2026

1 Mile

10K

View details for race Summer Sizzler- Orlando

Summer Sizzler- Orlando

Minneola, FL

Sunday, August 2nd, 2026

1 Mile

10K

View details for race Summer Sizzler- Orlando

Preseason Preview

Wildwood, FL

Saturday, August 8th, 2026

5K

View details for race Preseason Preview

Hot August Night Trail Race

Inverness, FL

Saturday, August 8th, 2026

Ultra

10 Miles

Trail

View details for race Hot August Night Trail Race

$AdventHealth Cool Sommer Mornings Triathlon\Duathlon\5K Series #3 logo$

AdventHealth Cool Sommer Mornings Triathlon\Dua...

Clermont, FL

Sunday, August 9th, 2026

5K

Ultra

Trail

View details for race AdventHealth Cool Sommer Mornings Triathlon\Duathlon\5K Series #3

Keel Farms Brew Run 5k

Plant City, FL

Saturday, August 15th, 2026

5K

View details for race Keel Farms Brew Run 5k

Upcoming Races Near Winter Garden, FL