196 Upcoming 5K Races Near Windermere, FL

11th Annual Umatilla Kiwanis 5K for the Kids

Umatilla, FL

Saturday, November 7th, 2026

View details for race 11th Annual Umatilla Kiwanis 5K for the Kids

Jack and Allie Superhero 5K

Clermont, FL

Saturday, November 7th, 2026

View details for race Jack and Allie Superhero 5K

WGPAL Donut Dash 5K

Winter Garden, FL

Saturday, November 7th, 2026

View details for race WGPAL Donut Dash 5K

BIGFOOT CHALLENGE 5k Veterans Day Run/Walk 5:00Pm

Clermont, FL

Wednesday, November 11th, 2026

1 Mile

View details for race BIGFOOT CHALLENGE 5k Veterans Day Run/Walk 5:00Pm

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Tunnel to Towers 5K Run & Walk - The Villages, FL

The Villages, FL

Saturday, November 14th, 2026

Fast

View details for race Tunnel to Towers 5K Run & Walk - The Villages, FL

Victoria Helping Veterans- First Annual Battle ...

Kissimmee, FL

Saturday, November 14th, 2026

View details for race Victoria Helping Veterans- First Annual Battle Buddy 5k

AdventHealth Presents the Central Florida Legen...

DeBary, FL

Saturday, November 14th, 2026

Marathon

Half

Fast

View details for race AdventHealth Presents the Central Florida Legends Marathon, Half Marathon and 5K

Gobbler 5K, 10K, & 13.1 at Lake Beresford Park,...

Deland, FL

Saturday, November 14th, 2026

10K

Half

View details for race Gobbler 5K, 10K, & 13.1 at Lake Beresford Park, Deland, FL (46S50)

Save the Manatee 5K

Orange City, FL

Sunday, November 15th, 2026

Trail

View details for race Save the Manatee 5K

The Keri Anne DeMott Foundation's World Day of ...

Orlando, FL

Sunday, November 15th, 2026

10K

View details for race The Keri Anne DeMott Foundation's World Day of Remembrance 5K and 10K

Hunger Run 5K at the Waterfront

Clermont, FL

Friday, November 20th, 2026

View details for race Hunger Run 5K at the Waterfront

Gobbler 5K, 10K, & 13.1M at DeBary, FL (47)

DeBary, FL

Saturday, November 21st, 2026

10K

Half

View details for race Gobbler 5K, 10K, & 13.1M at DeBary, FL (47)

Celebration 10K & 5K Pancake Run and Walk prese...

Celebration, FL

Saturday, November 21st, 2026

10K

Fast

View details for race Celebration 10K & 5K Pancake Run and Walk presented by the Rotary Club of Celebration

5K with the 5-0

Oakland, FL

Saturday, November 21st, 2026

Trail

View details for race 5K with the 5-0

Formosa Wine Run Turkey Trot 5k

Kissimmee, FL

Sunday, November 22nd, 2026

1 Mile

View details for race Formosa Wine Run Turkey Trot 5k

CINNAMON ROLL 5K

Plant City, FL

Thursday, November 26th, 2026

View details for race CINNAMON ROLL 5K

Ultra Ultras Turkey Trot 5k

Lake Wales, FL

Thursday, November 26th, 2026

Trail

View details for race Ultra Ultras Turkey Trot 5k

NSB Thanksgiving Gobble Wobble 5k - 2026

New Smyrna Beach, FL

Thursday, November 26th, 2026

View details for race NSB Thanksgiving Gobble Wobble 5k - 2026

AdventHealth Groveland Turkey Trot 5K & 10K pre...

Groveland, FL

Thursday, November 26th, 2026

10K

View details for race AdventHealth Groveland Turkey Trot 5K & 10K presented by LiveTrends Design Group

Turkey Day 5K Clermont

Clermont, FL

Thursday, November 26th, 2026

View details for race Turkey Day 5K Clermont

Turkey Trot 5k DeBary

Deland, FL

Thursday, November 26th, 2026

View details for race Turkey Trot 5k DeBary

Rise & Trot

Orlando, FL

Thursday, November 26th, 2026

View details for race Rise & Trot

All Turkey Trots

Deland, FL

Thursday, November 26th, 2026

View details for race All Turkey Trots

The Ritz-Carlton Gobbler 5K & Master Yoga Class

Orlando, FL

Thursday, November 26th, 2026

View details for race The Ritz-Carlton Gobbler 5K & Master Yoga Class

Turkey Trot Oviedo

Oviedo, FL

Thursday, November 26th, 2026

View details for race Turkey Trot Oviedo

Gobbler 5K, 10K, & 13.1M at Deltona, FL (48)

Deltona, FL

Saturday, November 28th, 2026

10K

Half

View details for race Gobbler 5K, 10K, & 13.1M at Deltona, FL (48)

OUC Orlando Half Marathon Weekend

Orlando, FL

Saturday, December 5th, 2026

Half

View details for race OUC Orlando Half Marathon Weekend

Holiday 5K, 10K, & 13.1M at DeBary, FL (49)

DeBary, FL

Saturday, December 5th, 2026

10K

Half

View details for race Holiday 5K, 10K, & 13.1M at DeBary, FL (49)

Your Next Step is the Cure 5K

Plant City, FL

Saturday, December 5th, 2026

View details for race Your Next Step is the Cure 5K

Deltona Jingle Jog 5K

Deltona, FL

Saturday, December 12th, 2026

View details for race Deltona Jingle Jog 5K

2026 Jingle Bell Run - Orlando, FL

Orlando, FL

Saturday, December 12th, 2026

1 Mile

View details for race 2026 Jingle Bell Run - Orlando, FL

Keel Farms Christmas Wine Run 5k

Plant City, FL

Saturday, December 12th, 2026

1 Mile

View details for race Keel Farms Christmas Wine Run 5k

Medal Madness 5K, 10K, & 13.1M at Deland, FL (50)

Deland, FL

Saturday, December 12th, 2026

10K

Half

View details for race Medal Madness 5K, 10K, & 13.1M at Deland, FL (50)

AdventHealth Santa's Twilight 5K - Cocoa Village

Cocoa, FL

Saturday, December 12th, 2026

View details for race AdventHealth Santa's Twilight 5K - Cocoa Village

Stuff Your Face Race

Orlando, FL

Saturday, December 12th, 2026

1 Mile

View details for race Stuff Your Face Race

ITMS Howl-iday Hustle, Run, Walk, and Play!

Winter Springs, FL

Saturday, December 12th, 2026

View details for race ITMS Howl-iday Hustle, Run, Walk, and Play!

AdventHealth Howey-in-the-Hills Reindeer Dash 5...

Howey-in-the-Hills, FL

Saturday, December 12th, 2026

Trail

View details for race AdventHealth Howey-in-the-Hills Reindeer Dash 5K presented by LiveTrends Design Group

Naughty or Nice 5K - Lake Mary

Lake Mary, FL

Sunday, December 13th, 2026

View details for race Naughty or Nice 5K - Lake Mary

Candy Cane Course - Orlando

Orlando, FL

Sunday, December 13th, 2026

1 Mile

10K

View details for race Candy Cane Course - Orlando

Holiday 5K, 10K, & 13.1M at DeBary, FL (51)

DeBary, FL

Saturday, December 19th, 2026

10K

Half

View details for race Holiday 5K, 10K, & 13.1M at DeBary, FL (51)

Mount Dora Half Marathon & 5K

Mount Dora, FL

Saturday, December 19th, 2026

10K

Half

View details for race Mount Dora Half Marathon & 5K

Santa Hustle Orlando

Kissimmee, FL

Saturday, December 19th, 2026

10K

View details for race Santa Hustle Orlando

Santa's Run Fest

Winter Haven, FL

Saturday, December 19th, 2026

15K

10K

Trail

View details for race Santa's Run Fest

AdventHealth Santa's Twilight 5K - Downtown Cle...

Clermont, FL

Saturday, December 19th, 2026

View details for race AdventHealth Santa's Twilight 5K - Downtown Clermont

Holiday Stress Buster 5K - 14th Annual

Lake Helen, FL

Thursday, December 24th, 2026

View details for race Holiday Stress Buster 5K - 14th Annual

Holiday 5K, 10K, & 13.1M at Deltona, FL (52)

Deltona, FL

Saturday, December 26th, 2026

10K

Half

View details for race Holiday 5K, 10K, & 13.1M at Deltona, FL (52)

The Ritz-Carlton Winter GLO 5k

Orlando, FL

Saturday, December 26th, 2026

View details for race The Ritz-Carlton Winter GLO 5k

Holiday Five

Winter Park, FL

Sunday, December 27th, 2026

Ultra

Marathon

Half

Trail

View details for race Holiday Five

Cheers to New Year's 5k Run/Walk - Orlando

Kissimmee, FL

Saturday, January 2nd, 2027

View details for race Cheers to New Year's 5k Run/Walk - Orlando

Game On! Run for Responders 5K

Cocoa, FL

Saturday, January 2nd, 2027

View details for race Game On! Run for Responders 5K

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