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7 running, walking, cycling, and other events in The Villages, Florida

From big races to Saturday morning group runs—find running, walking, cycling, and wheelchair events and connect with the local endurance sports community.

  • Hearts for Our Hospital Bicycle Challenge [raceroster.com]

    Sat, Nov 08, 2025

    Cycling Run

    Bonneau Ln, The Villages, Florida, United States
    OpenStreetMap Google Maps
  • Running with the Herd 5k [runningwiththeherd5k.com] [Register at runsignup.com]

    Sat, Feb 21, 2026 at 8:00 AM

    Description

    Join us for our 9th annual Running with the Herd 5k where there is fun for all ages! Aside from our main event, we will host a "Stampede Sprint" 100 Meter race for participants 10 and under as well...

    Join us for our 9th annual Running with the Herd 5k where there is fun for all ages! Aside from our main event, we will host a "Stampede Sprint" 100 Meter race for participants 10 and under as well as a "Herd Hurdle Havoc" Obstacle Course for participants Ages 3-12.

    All participants in the Stampede Sprint and Herd Hurdle Havoc Obstacle Course will receive a plastic participation medal.

    Registered Runners in the 5k Race will receive a *T-shirt (*must register before January 26, 2026) and those who complete the race will receive a 2026 Finisher medal.

    If you have a child running the 5k race and they are in 17 or younger, registration is $25. Adult registration is $35. Registration includes Finisher Medal and *T-Shirt (*ALL must register before January 26, 2026).

    We will have awards in the 5k race for men overall, women overall and 1st, 2nd, and 3rd place in each age group.

    Packet Pickup

    On Friday, February 20, 2026, we will have Packet Pickup at The Villages Charter Middle School Buffalo Ridge Campus (251 Buffalo Trail, The Villages, FL 32162) from 9:00am to 3:00pm. We will also have packet pickup starting at 6:30am on Saturday, the day of the race.

    If you haven't registered yet or have friends/family who are looking to register, there will be registration available at packet pickup on Friday as well as Saturday morning from 7:00am to 7:45am. Acceptable forms of payment will be cash and credit card. If paying by cash, please have the exact amount as we may not be able to make change.

    5k Run

    361 Buffalo Trail, The Villages, Florida, 32162, United States
    OpenStreetMap Google Maps
  • Buffalo Stroll - Autism Awareness 5k and Family Fun Event [runsignup.com]

    Sat, Apr 11, 2026 at 8:00 AM

    Description

    Lace up for a cause! The Buffalo Stroll features both a 5k timed race and a 100-meter dash.

    Stick around after the race for our Family Fun Event, complete with bounce houses, face painting, and...

    Lace up for a cause! The Buffalo Stroll features both a 5k timed race and a 100-meter dash.

    Stick around after the race for our Family Fun Event, complete with bounce houses, face painting, and balloon art.

    Plus, explore our Services Showcase to connect with local businesses that serve the autism community.

    Registration for the 5k

    • Registration fee is $35. $10 discount for participants under 17 and under.

    • Registration Fee includes t-shirt and bid for timed race. T-shirts available while supplies last. Register by March 20 to be guaranteed a race t-shirt.

    Pre-Registered Packet Pick Up:

    Packet pick up will be on Friday, April 10 from 8:30am to 2:30pm at The Villages Charter School Autism Center, 420 Village Campus Circle, The Villages, FL 32162. Packets will also be available at the race site the morning of the event starting at 7:15 am if you are not able to make it to early pick up on Friday. You may also have a friend or family member pick yours up if you are unable to do so.

    5k Run

    361 Buffalo Trail, The Villages, Florida, 32162, United States
    OpenStreetMap Google Maps
  • Walk In My Shoes 2026 - The Villages [laurenskidswalk.org] [Register at runsignup.com]

    Wed, Apr 15, 2026 at 9:00 AM

    Description

    Join the Lauren’s Kids foundation and thousands of walkers across the state for the 2026 Walk in My Shoes 1,500-mile trek across Florida. April is National Sexual Assault Awareness Month and National...

    Join the Lauren’s Kids foundation and thousands of walkers across the state for the 2026 Walk in My Shoes 1,500-mile trek across Florida. April is National Sexual Assault Awareness Month and National Child Abuse Prevention Month — every step counts in the fight to prevent child sexual abuse and help survivors heal.

    WALK IN MY SHOES THE VILLAGES

    Date: Wednesday, April 15th, 2026

    Start location: AVIV Clinics, 2955 Brownwood Blvd, The Villages, FL 32163

    Registration Begins: 9:00 AM

    Walk Start: 10:00 AM

    Details:

    Join us for a 5-mile walk to Publix Super Market at Trailwinds Village (5810 Seven Mile Dr Wildwood, FL 34785) — with the opportunity to stop or continue walking our full 9-mile route to Publix Super Market at Colony Plaza (327 Colony Blvd, The Villages, FL 32162)!

    An UBER code will be provided to walkers to cover the cost of a ride back from the walk.

    9 Miles Trail Walk

    2955 Brownwood Blvd, The Villages, Florida, 32163, United States
    OpenStreetMap Google Maps
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