4 running events in Kent County, Maryland
From big races to Saturday morning group runs—find running events and connect with the local endurance sports community.
Kent County
4 events in Kent County-
Fri, May 22, 2026 at 5:30 PMSee full details
The Sneaker Creeper was started by Dixon Valve & Coupling back in 1988, which means we are currently celebrating over 30 years of fun and fundraising!
All proceeds from this event benefit our local elementary school, Henry Highland Garnet Elementary, a Title 1 School. Funds are used to support school events, assemblies and extracurricular activities through the PTA.
This annual community-wide event is meant to enhance and encourage learning, sportsmanship, friendship and fitness, while having a whole lot of fun along the way. This event also kicks off the Chestertown Tea Party Festival.
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Sat, May 30, 2026 at 8:00 AMSee full details
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!
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Sat, Oct 03, 2026 at 8:00 AMSee full details
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/.
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Sat, Oct 10, 2026 at 8:00 AMSee full details
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.