Chestertown Challenge Half Marathon Run and 5K Run/Walk
Chestertown Challenge Half Marathon Run and 5K Run/Walk is a running race on October 11, 2026 in Chestertown, MD, with entry fees from $25 to $50.
- Date
- October 11, 2026 (80 days to go)
- Location
- Wilmer Park, Chestertown, MD
- Price
- $25–$50
- Sport
- Running
From the Organizer
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 in 1984 to help children and adults with disabilities enhance their social and developmental growth. KART uses a multi-faceted program involving therapeutic horseback riding, barn management, and caring for the horse.
Packet Pickup: All race packets can be picked up on Sunday morning starting at 8 a.m. Race day registration will also be accepted at this time.
Directions: Wilmer Park is located across the street from address 400 South Cross Street, Chestertown, MD. For directions, use your GPS or MapQuest.
Awards: Unique awards for overall male and female winners in the Half Marathon and 5K Run. Awards presented to the top 2 in 10-year age groups in the Half Marathon and 5K Run. Awards to top 2 male and female finishers in the 5K walk. 5K awards will be presented after the last participant finishes. Half Marathon awards will be presented 3 hours after start.
Course: The event starts and finishes at Wilmer Park. The course has gentle rolling terrain and is run entirely on paved country roads.
Course Records: Half Marathon: Male - Hasan Butler - 1:21:27 - 2014, Female – Meredith Tulio - 1:28:29 - 2018. 5K Run: Male - Jesse Goodyear - 17:50 - 2015, Female – Lisa Victorius - 20:50 - 2017
Amenities: Quality “Chestertown Challenge Half Marathon & 5K Run/Walk” Tech Shirts guaranteed to all participants registered by Monday, September 30th. Food and refreshments at the finish line! Police controlled roads, mile markers and directional arrows on road.
Water stops: Water stops will be located at approximately every two miles on the Half Marathon course, at the turnaround of the 5K, and at the start/finish.
Restrooms: Restrooms will be available at the start/finish and on the Half Marathon course.
Spectators: While you're waiting for your friends or family members to complete the race, enjoy the beautiful historic Chestertown sites on the Chester River. Visit www.kentcounty.com/tourism.
Hotels/Motels/Bed & Breakfast: Visit the following websites for a complete list of hotels/motels and bed & breakfast in the Chestertown and Rock Hall area.,
www.kentcounty.com/lodging/rockhall_lodging.php
Inns & Bed and Breakfast in Chestertown, Maryland
Events
Weather
Typical Conditions
It's too far out for a forecast, so here's what weather on this date is normally like in the area. A race day forecast will replace this as race week approaches.
Typical High
69°
Typical Low
50°
Chance of Rain
27%
Based on US Climate Normals data from Chestertown, 2 mi from the venue.
Host City
About Chestertown, MD
City Elevation
9 ft
Nearest Airport
BWI
Baltimore/Washington International Thurgood Marshall Airport · 31 mi
Time Zone
Eastern Time
From Endurance Grid
Line up lodging and travel early to lock in your race weekend.
Race Location
Your Next Start Line
What Are You
Waiting For?
Every finish line starts with a single decision. Claim your spot at Chestertown Challenge Half Marathon Run and 5K Run/Walk, put it on the calendar, and turn “someday” into a start date.
80
Days to train
- Race
- Chestertown Challenge Half Marathon Run and 5K Run/Walk
- Date
- October 11, 2026
- Location
- Wilmer Park, Chestertown, MD
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From Endurance Grid
About This Sport
Endurance Grid is here to help you understand the sport, decide if it’s the right fit, and learn how to prepare. For course distances, logistics, and race-day specifics, always defer to the race organizer’s event page.
With running, there's a distance for every fitness level, a community at every start line, and nothing beats the feeling of crossing a finish line you trained for.
Running is an endurance sport that rewards consistency, and showing up every week compounds in ways that will surprise you.
Running
From 5K to marathon, running races are an accessible entry point into endurance sport. There's a distance for every fitness level and a community at every start line.
Coming Up
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Hart-Miller Island Run
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Plan your trip
Make it a Racecation
Coming from out of town? There's more to Chestertown than race day. We'll help you line up nearby lodging, flights, a rental car, and things to do so you can make the most of your racecation.
Plan your trip to ChestertownFrequently Asked Questions (FAQs)
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Chestertown Challenge Half Marathon Run and 5K Run/Walk
Oct 11, 2026