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  • Distance: 940 m
    Sat, Oct 03, 2026 at 8:00 AM

    The Waterman’s Triathlons are nestled on the Eastern Shore of Maryland in picturesque Rock Hall, MD. Just 18 miles from Baltimore “as the fish swims” (put your bike rack on a boat!), Rock Hall is one of the friendliest, most laid back towns anywhere…and is full of history. George Washington took the Annapolis Ferry to Rock Hall nearly ten times before heading to Philly on horseback to work out America’s Independence! The time trial swim takes place in Rock Hall Harbor on the Chesapeake Bay, protecting athletes from any serious wind or chop. The bike course is a triathlete’s dream with beautiful ribbons of pavement and wide shoulders throughout most of the rural course. The run course is pancake flat and takes athletes through the quaint nautically themed neighborhoods and side roads of Rock Hall, MD.

    This race is worth the trip to Maryland’s Eastern Shore. Check out our race videos HERE and see why athletes consistently come back year after year to race. Don’t miss out, register today.

    For further race details go to https://kineticmultisports.com/races/watermans/.

    See full details
    RunSwimTriathlon via RunSignup
  • Distance: 16.1 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: 18.3 km
    Sun, Dec 27, 2026 at 8:45 AM

    Come out and enjoy this scenic and varied terrain route! You’ll traverse through a forest and along a stretch of sand, with stunning views of the Chesapeake Bay Bridge during part of the race.

    5k10kRunVirtual via RaceRoster
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