In 28 days · Sun, Oct 11, 2026
Don't let race day sneak up
One email during race week. That's it.
When
Sunday, October 11th, 2026
Where
Wilmer Park, Chestertown MD
Distances
Half · 5K
Typical weather
57–69°F · low rain risk
See last 10 years
On this date: rain 3 of the last 10 years
2025
50–69°F
dry
2024
49–65°F
dry
2023
53–68°F
dry
2022
51–68°F
dry
2021
62–74°F
dry
2020
63–71°F
rain
2019
55–71°F
dry
2018
72–78°F
rain
2017
65–73°F
rain
2016
50–63°F
dry
Best months to race in Maryland →
About this race
Event Overview
- Date: 2026-10-11
- Location: Wilmer Park, Chestertown, MD
- Race Starts: Half Marathon Run & 5K Run/Walk at 9 a.m.
- Registration Opens: At 8 a.m.
Benefits
- Supported Charity: Kent Association of Riding Therapy, Inc. (KART)
- Mission: Founded in 1984 to help children and adults with disabilities enhance their social and developmental growth.
- Programs: Involves therapeutic horseback riding, barn management, and caring for the horse.
- Silent Hero Donation: Can’t make this event but would like to show your support? Register as a Silent Hero!
Registration Information
- Race Day Registration: Available on race day!
- Packet Pickup: Starts at 8 a.m. on race day.
- Location: Wilmer Park, Chestertown, Maryland.
- Food: Food for purchase will be available!
Awards
- Overall Winners: Unique awards for overall male and female winners in the Half Marathon and 5K Run.
- Age Group Awards: Awards presented to the top 2 in 10-year age groups in the Half Marathon and 5K Run.
- 5K Walk Awards: Awards to top 2 male and female finishers in the 5K walk.
- Award Presentation: 5K awards will be presented after the last participant finishes: Half Marathon awards after 3 hours.
Course Information
- Start/Finish: The event starts and finishes at Wilmer Park.
- Terrain: Gentle rolling terrain 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.
- Water Stops: Located approximately every two miles on the Half Marathon course and at the 5K turnaround.
Amenities
- Shirts: Quality "Chestertown Challenge Half Marathon & 5K Run/Walk" tech shirts guaranteed to all participants registered by September 30th.
- Refreshments: Food and refreshments at the finish line!
- Course Support: Police controlled roads, mile markers, and directional arrows on road.
- Restrooms: Available at start/finish and along the Half Marathon course.
Directions
- Location: Wilmer Park is located across the street from 400 South Cross Street, Chestertown, MD.
- Map: For directions, use your GPS or MapQuest.
Spectators
- Attractions: While waiting for participants, enjoy the beautiful historic Chestertown sites on the Chester River.
- Visitor Information: Visit www.kentcounty.com/tourism for more details.
Accommodations
- Local Listings: Visit the following websites for hotels/motels and bed & breakfasts in the Chestertown and Rock Hall area.
- Rock Hall Lodging: www.kentcounty.com/lodging/rockhall_lodging.php
- Chestertown Inns: Inns & Bed and Breakfast in Chestertown, Maryland
- Red Roof Inn: Red Roof Inn & Suites Chestertown - ReservationDesk.com
- Comfort Inn: Comfort Inn & Suites Chestertown - ReservationDesk.com
Additional Information
- More Info: Visit the race website for full details: Chestertown Challenge Half Marathon Run and 5K Run/Walk.
Course map
Hotels for race weekend
Live prices near the start line, Oct 10 – 12, 2026.
Train with a club
Run clubs near Chestertown to train with before race day.
See all run clubs near Chestertown →
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