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  • Distance: 5.8 km from Winchester
    Sat, Aug 08, 2026 at 7:30 AM

    Come enjoy the scenic routes at Third Winchester Battlefield!

    Walkers are welcome to attend this event.

    5k10kHalf MarathonRunVirtual
  • Distance: 11.8 km from Winchester
    Thu, Nov 26, 2026 at 8:00 AM

    Get ready to gobble up the fun this Thanksgiving! Start your holiday with our festive Thanksgiving Day 5K at beautiful Sherando Park. Whether you’re racing or strolling, you’ll love our scenic course featuring the track, pavement, and woodland trails — it’s the perfect mix of terrain and fall color. Work up an appetite before the feast, make memories, and kick off your day with fun, fitness, and festive vibes!

    No Race Day Registration - register early!!

    3.1 Miles5kFun RunKidsRunTrail
  • Distance: 12 km from Winchester
    Sat, Sep 26, 2026 at 8:30 AM

    Join us for our annual trail race at Sherando Park—and get ready for an unforgettable fall challenge!

    Now in its 7th year, this mixed-surface four-mile trail race takes runners through the paved paths and wooded trails of Sherando Park’s scenic mountain bike trail system. Whether you’re a seasoned trail runner or tackling your first off-road race, you’ll enjoy a challenging and rewarding course surrounded by crisp fall air and vibrant autumn colors.

    ✨ New for 2026: We’re excited to introduce a Mountain Bike Time Trial to this event! Cyclists will have the opportunity to test their speed and skills on the Sherando Park mountain bike trails in a timed, individual-start format, adding a whole new level of competition and excitement to race day.

    Proceeds from all events will benefit the I’m Just Me Movement, supporting confidence, inclusion, and self-acceptance in our community.

    Not up for four miles on trails?

    We’ve got you covered! We’ll also offer an untimed One Mile Fun Run/Walk, perfect for participants who want to support the cause while enjoying a shorter, paved option. The one-mile course will be an out-and-back on the paved Sherando Park path, with a course marshal stationed at the turnaround. Mile participants will start just before the four-mile race.

    Date: Saturday, September 26th

    Time: 8:30 AM

    Location: Sherando Park - Mountain Bike Trails

    Race Day Registration & Packet Pickup: Saturday, September 26th: 7-8 am at the Race Start/Finish area

    1 Miles4 Miles5.3 MilesFun RunRunTrailWalk

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