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  • Distance: 21 km
    Sat, Aug 08, 2026 at 9:00 AM

    Join us on Saturday August 9thth for the Annual Running Hot Clayton Fire 5K.

    Post race Fiesta back at the station!

    5kRun via RunSignup
  • Distance: 20.3 km
    Sun, Oct 11, 2026 at 9:00 AM

    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

    See full details
    3.1 Miles5k13.1 MilesHalf MarathonRunWalk via RunSignup
  • Distance: 14.3 km
    Sat, Oct 17, 2026 at 8:00 AM

    Be a part of a celebration of the parks in beautiful Queen Anne's County, Maryland. Just over the Chesapeake Bay Bridge, on the Eastern Shore of Maryland, this straight forward event will be a great way to end your season!

    Come experience the Matapeake Beach area with a 1/2 mile swim in the Chesapeake Bay, a 12 mile out-and-back bike ride along the straight and flat Route 8 (Romancoke Road) corridor, and then it's back out for an out-and-back 3.1 mile run on the South Island Trail. Once you see the views from here, you'll be sure to be back for training!!

    See full details
    12.5 Miles15.6 Miles15.9 MilesDuathlonRunSwimTrailTriathlon via RunSignup
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