Events in Kent County, Maryland | 2026-2027

36th Annual Sneaker Creeper [runsignup.com]

Fri, May 22, 2026 at 5:30 PM

Description

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...

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.

1 Miles Run

Kent County, Maryland, 21678, United States
OpenStreetMap Google Maps

Rock Hall Triathlon [kineticmultisports.com] [Register at runsignup.com]

Sat, May 30, 2026 at 8:00 AM

Description

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...

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!

Run Swim Triathlon

21096 W. Sharp St., Kent County, Maryland, 21661, United States
OpenStreetMap Google Maps

Betterton SwimFest [frenchcreekracing.com] [Register at runsignup.com]

Sat, May 30, 2026 at 8:30 AM

Description

Welcome to the 2026 Betterton SwimFest brought to you by French Creek Racing!

This SwimFest event at Betterton Beach, MD has three distances (plus options to combine events for longer distance)...

Welcome to the 2026 Betterton SwimFest brought to you by French Creek Racing!

This SwimFest event at Betterton Beach, MD has three distances (plus options to combine events for longer distance) including:

800 meter swim (1 loop)

1600 meter swim (2 loops)

2400 meter swim (3 loops)

For an extra challenge, race in all 3!

Register today for your choice of races!

Online Registration Closes Thursday, May 28 at 12 midnight.

Check-in is available from 6:30AM to 8:00AM on Saturday May 30. All racers should check in when they arrive.

NO REFUNDS and no rain date. In the event of inclement weather, entries will roll into next year's race, or you may transfer your registration to another FCR event.

Historical water temperature varies, but has averaged between 65-75F for this date over the past 4 years. Wetsuits will be allowed with water temps below 78.0 degrees. You can find real time water temperature updates here.

Swim

Kent County, Maryland, 21610, United States
OpenStreetMap Google Maps

Waterman's Triathlon Festival [kineticmultisports.com] [Register at runsignup.com]

Sat, Oct 03, 2026 at 8:00 AM

Description

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...

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/.

Run Swim Triathlon

21096 W. Sharp St., Kent County, Maryland, 21661, United States
OpenStreetMap Google Maps

Tom McHugh Arts Scholarship 5K Run/Walk [runsignup.com]

Sat, Oct 10, 2026 at 8:00 AM

Description

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...

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 Info@TCREventManagement.com

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.

3.1 Miles 5k Run Virtual Walk

Kent County, Maryland, 21661, United States
OpenStreetMap Google Maps

5 events in Kent County, Maryland

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