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Chestertown Challenge Half Marathon Run and 5K Run/Walk
Chestertown, Maryland · Sunday, October 11, 2026 · Half Marathon, 5K
Official race page & registration ↗Chestertown Challenge Half Marathon Run and 5K Run/Walk takes place on Sunday, October 11, 2026 in Chestertown, Maryland. The race offers 2 distances: Half Marathon, 5K. For anyone travelling in, Edgewood is about 18 miles away and Baltimore is about 29 miles away.
It is one of 110 races on the Maryland calendar that October. At $25, entry sits below the $30 median for a Maryland half marathon.
- Date
- Sunday, October 11, 2026
- Location
- Chestertown, Maryland
- Distances
- Half Marathon, 5K
- Entry fee
- from $25
Listing from the 2026 race calendar, refreshed nightly. Details can change: confirm date and entry on the official race page before travelling. Spot an error? Tell us here.
Making a race weekend of it?
Stay near the start line in Chestertown: check in Oct 10, out Oct 12.
Common questions
When is Chestertown Challenge Half Marathon Run and 5K Run/Walk?
Chestertown Challenge Half Marathon Run and 5K Run/Walk is scheduled for Sunday, October 11, 2026.
Where is Chestertown Challenge Half Marathon Run and 5K Run/Walk held?
Chestertown Challenge Half Marathon Run and 5K Run/Walk is held in Chestertown, Maryland. It is about 18 miles from Edgewood and 29 miles from Baltimore.
What distances does Chestertown Challenge Half Marathon Run and 5K Run/Walk offer?
The listed distances are Half Marathon, 5K.
How much does Chestertown Challenge Half Marathon Run and 5K Run/Walk cost?
Entry is listed from $25. Check the official race page for the current price, which usually rises closer to race day.
How do I register for Chestertown Challenge Half Marathon Run and 5K Run/Walk?
Registration is handled on the official race page, linked at the top of this listing. Entry can close early if the race sells out.
More races nearby
- Oct 112026 Robert I. Damie Race For Our KidsBaltimore, MD
- Oct 11Falkorburg CrossStevenson, MD
- Oct 11Lighthouse Lookout 5k & 10kScotland, MD
- Oct 11Rick O'Donnell Memorial 5 Mile Trail Run and Ultra ChallengeMount Airy, MD
- Oct 11Rocky Gap 25K, 50K, Relay Trail RunFlintstone, MD
See every race on the Maryland calendar, Maryland Half Marathons, Maryland 5Ks, or use the Race Finder for maps and filters.