Chestertown Challenge Half Marathon Run and 5K Run/Walk

The Rock Hall Triathlons are nestled on the edge of the Eastern Shore of Maryland in picturesque Kent County and only 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 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. Watch last years race video, then register and plan your trip to Rock Hall, MD!

Benefits: Benedictine - Learning for Living

Presented by: Godfrey’s Farm

When: Saturday, June 13, 2026, 9 A.M. Rain or Shine. Healthy Kids Run (10 & under) starts at 8:55 A.M.

Where: Godfrey’s Farm, 302 Leager Road, Sudlersville, MD – Visit godfreysfarm.com for complete details.

Registration:

• $30 plus fees until May 13 (t-shirt order date)

• $35 plus fees May 14 through June 1 (t-shirt subject to availability)

• $40 plus fees June 1 through event day. Registration starts 7:30 A.M. (t-shirt subject to availability)

Packet Pick Up: Godfrey's Farm, Friday June 12 8am - 6pm and Race Day 7:30 AM

Silent Hero: Can’t make the event but would like to show your support? Register as a Silent Hero. We appreciate your support.

Awards:

• 5K run awards:

• Top 1, 2, and 3 male finishers

• Top 1, 2, and 3 female finishers

• Age group awards for the Top 1 male runner & Top 1 female runner in each group: 9 and under, 10-19, 20-29, 30-39, 40-49, 50-59, 60-69, 70 and over

• 5K walk awards:

• Top 5 male finishers

• Top 5 female finishers

• Ribbons to all Healthy Kids Run participants

Benefits: Benedictine is one of the most comprehensive providers of services for children and adults with developmental intellectual disabilities and autism. They offer a year-round educational program and 365-day residential program for students ages 5-21. Their students come from throughout Maryland, as well as adjoining states. Benedictine’s adult program provide community living, meaningful day, and employment services on the Eastern Shore and Annapolis. To learn more about the great work they do at Benedictine, please go to their website www.benschool.org.

Team Signup: Sign up as a team of 5 or more and get a discount on ALL of the registrations. Who can have the largest team?

Amenities: Quality EVENT SHIRTS to all participants as available. Sign up early to insure you get your preferred t-shirt! Festivities to include music, apple cider donuts, blueberry scones, fresh fruit, coupon for free ice cream or fruit slushie, prize drawings, and much more!

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!!