Maryland · Half Marathon · 5K Run · 5K Walk (plus Silent Hero donation entry)
Chestertown Challenge Half Marathon Run and 5K Run/Walk
Chestertown Challenge Half Marathon Run and 5K Run/Walk is a half marathon, 5K Run and 5K Walk (plus Silent Hero donation entry) event held in Chestertown, Maryland. It was last held on October 11, 2026 and is usually run in October; the next date hasn't been announced yet. About 109 runners take part across all distances.
- Usually held
- October
- Location
- Chestertown, MD
- Field size
- ~109 runners
Race details
- Last held
- October 11, 2026
- Usually held in
- October
- Location
- Chestertown, Maryland
- Distances
- Half Marathon, 5K Run, 5K Walk (plus Silent Hero donation entry)
- Field size
- About 109 runners
- Course
- Out-and-back course on paved rural roads outside Chestertown; organizer describes terrain as "gentle rolling"; no official elevation profile published.
- Registration
- runsignup.com
Registration, course & weather
- Registration status
- Registration status as last checked September 26, 2026: open
- Entry fee
- Listed fee for the longest distance, $54.50 (from runsignup.com, checked September 26, 2026)
- Start time
- 9:00 AM EDT
- Course profile
- Out-and-back course; Road surface; USATF certified
- Typical race-day weather
- about 63°F at the start, 82% humidity, 15 mph wind (based on the 2025 race day, measured near the city center rather than the exact start line; Open-Meteo, checked September 26, 2026)
About the Chestertown Challenge Half Marathon Run and 5K Run/Walk
Benefits: Kent Association of Riding Therapy, Inc. (KART) Registration opens at 8 a.m. - Half Marathon Run & 5K Run/Walk start at 9 a.m. Registration: Race day registration will be available! Packet pickup starts at 8 a.m. and races start at 9 a.m. at Wilmer Park, Chestertown, Maryland. Silent Hero Donation: Can't make this event but would like to show your support? Register as a Silent Hero! Food for Purchase will be available! Benefactor: Kent Association of Riding Therapy (KART) was founded …
More half marathons in Maryland
Coming up next, by confirmed date.
-
Schaeffer Half Marathon, 10K, 5K Trail RunGermantown, MDHalf Marathon3.2 Miles6.7 Miles13.5 Miles ~2 runners
-
Freedom is Never Free 5k, 10k, & HalfPotomac, MD10K5KHalf MarathonVirtual with Medal +2 more ~629 runners
-
Budds Creek Turkey Trot 5k, 10k, & HalfMechanicsville, MD10K5KHalf MarathonVirtual with Medal +2 more
-
NCR Marathon & Half Marathon (North Central Rail Trail)Sparks Glencoe, MDMarathonHalf Marathon ~2,000 runners
More upcoming races in Maryland
Keep exploring
- All races in Maryland
- 5Ks in Maryland 96 upcoming races
- 10Ks in Maryland 41 upcoming races
- Half Marathons in Maryland 19 upcoming races
- Marathons in Maryland 6 upcoming races
- 5Ks in the United States 6,000 upcoming races
- Half Marathons in the United States 1,668 upcoming races
- Fall Half Marathons
- October Half Marathons
- October races in Maryland
- Half Marathons in Virginia 40 upcoming races
- Half Marathons in Pennsylvania 40 upcoming races
- Half Marathons in West Virginia 18 upcoming races
- Half Marathons in Washington, DC 15 upcoming races
Guides from the RaceRove blog
- 8 min read How to Choose the Best Half Marathon for a PR, Racecation or 50-State Challenge The best half marathon depends on what you want from it. How to choose a course for a personal record, a race worth travelling for, or an efficient stop on a 50-state challenge.
- 7 min read How to Find a 5K, 10K, Half Marathon or Marathon Near You A practical way to find running races near you: pick a distance, decide how far you'll travel, read the listing properly and confirm the details before you register.
- 9 min read How to Run a Race in All 50 States How to plan a 50-state running challenge: set your own rules, group states into trips, build a calendar around the seasons, budget for it and keep track of every finish.
- Blog All guides Planning advice for finding, choosing and travelling to races.
Chestertown Challenge Half Marathon Run and 5K Run/Walk: common questions
- When is the Chestertown Challenge Half Marathon Run and 5K Run/Walk?
- The next date hasn't been announced in the listing yet. The race is usually held in October. Check the organiser's website for the official date.
- Where is the Chestertown Challenge Half Marathon Run and 5K Run/Walk held?
- In Chestertown, Maryland.
- What distances does the Chestertown Challenge Half Marathon Run and 5K Run/Walk offer?
- Half Marathon, 5K Run and 5K Walk (plus Silent Hero donation entry).
- How many people run the Chestertown Challenge Half Marathon Run and 5K Run/Walk?
- About 109 runners across all of its distances. That figure is an estimate of the field size, not an entry cap.
- How do I register for the Chestertown Challenge Half Marathon Run and 5K Run/Walk?
- Registration is handled by the organiser at runsignup.com. Entry fees, caps and deadlines are set there.
- Is registration open for the Chestertown Challenge Half Marathon Run and 5K Run/Walk?
- Registration status as last checked September 26, 2026: open. Listed fee for the longest distance, $54.50 (from runsignup.com, checked September 26, 2026).
- What time does the Chestertown Challenge Half Marathon Run and 5K Run/Walk start?
- 9:00 AM EDT.
- What is the course like at the Chestertown Challenge Half Marathon Run and 5K Run/Walk?
- Out-and-back course; Road surface; USATF certified.
- What is race-day weather usually like at the Chestertown Challenge Half Marathon Run and 5K Run/Walk?
- about 63°F at the start, 82% humidity, 15 mph wind (based on the 2025 race day, measured near the city center rather than the exact start line; Open-Meteo, checked September 26, 2026).
Plan this race in RaceRove
Save it to your plan, compare it with other races, check typical race-day weather and track your 50-state progress in the interactive app.