What race distances can I run in Chesapeake City?
Chesapeake City has 5K (3). The 5K is usually the easiest entry point if you are new, and the links above jump straight to each distance.
Maryland · Race calendar
2027 Running Races in Chesapeake City, Maryland
Upcoming running races in and near Chesapeake City, Maryland - 5Ks, 10Ks, half marathons and more, with dates, pricing, finish-time stats, start-line maps, and local run clubs to train with.
3 upcoming races · 1 with finish-time stats
By the numbers
The Biggest and Longest-Running
The Chesapeake City races that stand out on the numbers: the biggest field, and the longest unbroken run of editions.
Sun, Jun 6, 2027Pain in De Ass 5K Chesapeake City, MDRegistration opens Jan 31, 2027From $35Details Sun, Aug 8, 2027Run the Vineyards - Bohemia Manor Farm 5K & 8K Chesapeake City, MDFrom $44Details Sun, Aug 29, 2027Crush the Chesapeake 5K Chesapeake City, MDRegistration opens Feb 13, 2027From $25Details
Within 100 miles
Races in Nearby Cities
More race calendars close to Chesapeake City. Miles are measured center to center, so treat them as a rough guide.
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 Nov 12, 2026.
Common Questions About Racing in Chesapeake City
When is race season in Chesapeake City?
August is the busiest month for races in Chesapeake City, with 2 of the 3. If you are flexible on the date, that is the quickest way to narrow things down.
Where can I train for a race in Chesapeake City?
Browse Chesapeake City run clubs on RunSesh to find a training group at your pace.
Are there trail races near Chesapeake City?
Yes, one race around Chesapeake City gets you off the pavement: 1 is a trail race.