Chestertown Challenge Half Marathon Run and 5K Run/Walk

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/.

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.

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!!