Chestertown Challenge Half Marathon Run and 5K Run/Walk

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.

The 30th Annual Chestertown Tea Party

Distance Classic Race & Run for Radcliffe

Saturday, May 23, 2026

Radcliffe Creek School is excited to host the 30th Annual Chestertown Tea Party Distance Classic Race and Run for Radcliffe.

As is tradition, the run will help kick off Chestertown's Annual Tea Party Festival on Saturday, May 23, 2026! Hundreds of runners and walkers are slated to take off from Chestertown's Wilmer Park and trek along a 5K or a 10-mile path throughout the beautiful Kent County countryside.

As the only K-8 school on Maryland’s Eastern Shore focused on serving students with learning differences, Radcliffe Creek School (RCS) stands out as a critical resource for families across the State of Maryland and beyond, whose children have not found success in traditional learning environments.

When you participate in the Run for Radcliffe, you help fund scholarships for children with learning differences—such as dyslexia and ADHD—who rely on the research-backed methodologies and customized instruction that RCS provides to thrive in the classroom.

Registration will remain OPEN until right before the event on May 23rd. You will also be able to register in person on the day of the race (but don't wait until then - secure your spot for less AND a race shirt!)

In-Person Registration & Race Bib Pick-Up

Friday, May 22nd, 2026, from 3:00 pm - 6:00 pm

Radcliffe Creek School (201 Talbot Boulevard, Chestertown, MD 21620)

Saturday, May 23rd, 2026, beginning at 6:30 am

Wilmer Park (413 S Cross Street, Chestertown, MD 21620)

In-person registration & morning of registration costs will be an additional $5 + associated fees.

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/.