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Chestertown Challenge Half Marathon Run and 5K Run/Walk logo

Chestertown Challenge Half Marathon Run and 5K Run/Walk

Sun, Oct 11, 2026, 9:00 AM EDT

Location
Chestertown, MD
Wilmer Park, 21620
Type
RUN

Sign up and verify details on the organizer’s official page.

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Course feel, difficulty, and community fit are being added to this listing. Check back, and always confirm details on the official registration page.

Distances & registration

4 options

Registration for all distances is through the official signup link above.

  • 3.1 Miles

    Sun, Oct 11, 9:00 AM EDT · From $28.00

    Opens Dec 5, 2025, 7:00 PM EST · Closes Sep 20, 2026, 7:59 PM EDT

  • 3.1 Miles

    Sun, Oct 11, 9:00 AM EDT · From $28.00

    Opens Dec 5, 2025, 7:00 PM EST · Closes Sep 20, 2026, 7:59 PM EDT

  • 13.1 Miles

    Sun, Oct 11, 9:00 AM EDT · From $54.50

    Opens Dec 5, 2025, 7:00 PM EST · Closes Sep 20, 2026, 7:59 PM EDT

+ 1 more option
  • Silent Hero

    Sun, Oct 11, 9:00 AM EDT · From $33.30

    Opens Dec 6, 2025, 5:25 PM EST · Closes Oct 11, 2026, 5:00 AM EDT

Vibe Check

Steady Effort

Flat road course, longer distance

Based on terrain, weather, and distance data.

The course

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!

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

Red Roof Inn & Suites Chestertown - ReservationDesk.com

Comfort Inn & Suites Chestertown - ReservationDesk.com

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