When is race season in Winchester?
October is the busiest month for races in Winchester, with 2 of the 6. If you are flexible on the date, that is the quickest way to narrow things down.
Virginia · Race calendar
Running Races in Winchester, Virginia
Upcoming running races in and near Winchester, Virginia - 5Ks, 10Ks, half marathons and more, with dates, pricing, finish-time stats, start-line maps, and local run clubs to train with.
6 upcoming races · 3 with finish-time stats
By the numbers
The Biggest and Longest-Running
The Winchester races that stand out on the numbers: the biggest field, and the longest unbroken run of editions.
Mon, Jul 27, 2026SVR Richmond Marathon Group Training Program Winchester, VAFrom $25Register Mon, Aug 17, 2026Youth Running Club Winchester, VAFrom $65Details Sat, Sep 12, 2026Bill Meyer Invitational Winchester, VAPricing TBADetails Sat, Oct 10, 2026Fire and Rescue 5K Winchester, VAFrom $35Details Thu, Oct 29, 2026Halloween Scavenger Hunt Fun Run Winchester, VAFrom $5Details Sun, Dec 6, 2026SVR Winter Series Winchester, VAFrom $60Details
How we calculate these stats: RunSesh calculates these figures from the most recent published results of past editions, sourced from RunSignup. We show aggregates only: field size, winning and median times, and the cutoff. We never publish individual finisher tables. Last updated Sep 10, 2026.
Common Questions About Racing in Winchester
Are Winchester races beginner-friendly?
Yes, for the most part. Across the 3 races in Winchester with published results, the typical median finish is around 27:52, which means half of every one of those fields came in slower than that. Recreational runners and walk-runners are the bulk of these fields, not the exception.
Where can I train for a race in Winchester?
Browse Winchester run clubs on RunSesh to find a training group at your pace.