Chestertown Lions Club

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

Join the Tom McHugh Art Scholarship 5k

When: Saturday, October 10, 2026, 9:00 a.m. Rain or Shine. FREE Kiddie K Run (10 & under) starts at 8:45 a.m.

Where: Waterman’s Crab House & Dock Bar, 21055 East Sharp Street, Rock Hall, MD 21661.

Registration: $30 until Oct 3rd; $35 after and on event day. Registration starts 8:00 a.m. Questions? Contact [email protected]

Silent Hero: Can't attend but would like to show your support? Register as a silent hero. We appreciate your support!

Awards: Awards to overall male/female and master winners, top 3 male/female runners in 10-year age groups awards and top 5 male/female walk finishers. Ribbons to all Kiddie K finishers. The awards ceremony will be held immediately after last participant finishes.

SWAG: Quality "Tom McHugh Arts Scholarship" tech shirts for all of our registered participants.

Celebrate: FallFest is an annual celebration of family, community, and oysters. Live music, entertainment, vendors, artisans, and food will be offered. Rock Hall is a charming waterfront town on the Chesapeake Bay. More information can be found at www.rockhallfallfest.org or www.RockHallMD.com

Our Mission: The Tom McHugh Arts Scholarship has been created to support a student whose character aligns with the spirit of Tom McHugh, a creative artist, an inspirational storyteller, and a community enthusiast. * Proceeds from the 5K will benefit the Tom McHugh Arts Scholarship Award to be presented to a KCHS graduating senior pursuing studies in an Arts curriculum. A portion of the proceeds will also benefit the Rock Hall Elementary School Arts Program.

The website for the Scholarship Site is https://tommchughscholarship.com/

We will continue our Virtual Option!! Run anywhere you like on October 10th to celebrate with us! If you would like a shirt, please note that you will need to make arrangements with the Race Director to pick it up. Shirts will NOT be mailed.

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/.