2 events in Chestertown, Maryland
From big races to Saturday morning group runs—find 5k events and connect with the local endurance sports community.
Chestertown
2 events in Chestertown-
Sat, May 23, 2026 at 8:30 AMSee full details
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.
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Sun, Oct 11, 2026 at 9:00 AMSee full details
Benefits: Kent Association of Riding Therapy, Inc. (KART)
Registration opens at 8 a.m. - Half Marathon Run & 5K Run/Walk start at 9 a.m.
Registration: Race day registration will be available! Packet pickup starts at 8 a.m. and races start at 9 a.m. at Wilmer Park, Chestertown, Maryland.
Silent Hero Donation: Can't make this event but would like to show your support? Register as a Silent Hero!
Benefactor: Kent Association of Riding Therapy (KART) was founded in 1984 to help children and adults with disabilities enhance their social and developmental growth. KART uses a multi-faceted program involving therapeutic horseback riding, barn management, and caring for the horse.
Packet Pickup: All race packets can be picked up on Sunday morning starting at 8 a.m. Race day registration will also be accepted at this time.
Directions: Wilmer Park is located across the street from address 400 South Cross Street, Chestertown, MD. For directions, use your GPS or MapQuest.
Awards: Unique awards for overall male and female winners in the Half Marathon and 5K Run. Awards presented to the top 2 in 10-year age groups in the Half Marathon and 5K Run. Awards to top 2 male and female finishers in the 5K walk. 5K awards will be presented after the last participant finishes. Half Marathon awards will be presented 3 hours after start.
Course: The event starts and finishes at Wilmer Park. The course has gentle rolling terrain and is run entirely on paved country roads.
Course Records: Half Marathon: Male - Hasan Butler - 1:21:27 - 2014, Female – Meredith Tulio - 1:28:29 - 2018. 5K Run: Male - Jesse Goodyear - 17:50 - 2015, Female – Lisa Victorius - 20:50 - 2017
Amenities: Quality “Chestertown Challenge Half Marathon & 5K Run/Walk” Tech Shirts guaranteed to all participants registered by Monday, September 30th. Food and refreshments at the finish line! Police controlled roads, mile markers and directional arrows on road.
Water stops: Water stops will be located at approximately every two miles on the Half Marathon course, at the turnaround of the 5K, and at the start/finish.
Restrooms: Restrooms will be available at the start/finish and on the Half Marathon course.
Spectators: While you're waiting for your friends or family members to complete the race, enjoy the beautiful historic Chestertown sites on the Chester River. Visit www.kentcounty.com/tourism.
Hotels/Motels/Bed & Breakfast: Visit the following websites for a complete list of hotels/motels and bed & breakfast in the Chestertown and Rock Hall area.,
www.kentcounty.com/lodging/rockhall_lodging.php
Inns & Bed and Breakfast in Chestertown, Maryland
Red Roof Inn & Suites Chestertown - ReservationDesk.com
Comfort Inn & Suites Chestertown - ReservationDesk.com
Local Clubs & Organizations
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