HalfRuns
Chestertown Challenge Half Marathon Run and 5K Run/Walk

Chestertown Challenge Half Marathon Run and 5K Run/Walk

Chestertown Challenge offers a scenic country road half marathon benefiting therapeutic horseback riding.

Race Date

Oct 11, 2026

Location

Chestertown, MD

Standout60

Quick facts

Date
Sunday, October 11, 2026
Location
Chestertown, Maryland
Distance
Half marathon (13.1 mi) + 3.1 Miles, Silent Hero
Course
Loop Course
Terrain
Road
USATF certified
Yes
Finishers on record
646

Highlights

Good For

Beginner Friendly

Atmosphere

Local CommunityGreat SwagWell Organized

Course

Scenic Route

The Experience

The Chestertown Challenge Half Marathon, first run in 2010 and now in its 6th edition, winds through the picturesque Maryland countryside. Runners will experience the gentle rolling terrain of paved country roads, starting and finishing at the scenic Wilmer Park.

This event is more than just a race; it's a community effort supporting the Kent Association of Riding Therapy (KART), which provides therapeutic horseback riding for children and adults with disabilities. With a median field size of around 134 finishers, the race offers an intimate yet growing atmosphere, drawing participants from approximately 9 states.

Unique awards await overall winners and age group top finishers, with the 5K awards presented after the last participant crosses the line and the half marathon awards given three hours after the start. Participants can also register as a 'Silent Hero' to support KART even if they cannot attend.

Race-provided description

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!   Food for Purchase will be available! 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

Logistics

Race Day

Sunday, October 11, 2026

Start Time

9:00 AM

Giveaway

T-Shirt

Start Location

Wilmer Park, Chestertown, MD, 21620

Directions

Course Info

USATF Certified

Course Type

Loop Course

Terrain

road

Scenery

Rural

Surface

Paved

Difficulty

Rolling Hills

Net Drop/km

0 m (Flat)

Separation

0.0%

Also Offers

3.1 MilesSilent Hero

USATF Certified Course

MD24003NP · Chestertown Challenge Half

Relatively flat with minimal net elevation change. Loop course — start and finish are close together.

Course Map

1 other map for this race

Quality Score

Standout60
Methodology
Heritage12/20

6 years running

Size11/15

~134 finishers a year

Momentum5/5

growing or steady

Loyalty9/20

9% returning runners

Course & details10/15

USATF certified · 5 timing sources

National draw6/10

runners from 9 states

Front-pack speed3/5

winner 1:23:31

Weather5/10

typical high 68°F

Race Day Weather

5-year historical avg

Start (Low)

53°

Afternoon (High)

68°

Pleasant conditions — light layers at start, comfortable by finish

0.1"

Precipitation

10 mph

Wind

73%

Humidity

Historical Finish Times

How 646 finishers actually crossed the line across 6 years.

Most recent

2025

Total finishers

646

Median time

2:07:56

Latest turnout

67

States

20

10%
25%
75%
90%
1:10p50 median ≈ 2:053:40

Turnout by year

20102025

'10'11'12'23'24'25
See full results

Hover the histogram to inspect specific finish times.

Race Photos

Frequently asked

When is the Chestertown Challenge Half Marathon Run and 5K Run/Walk?

The Chestertown Challenge Half Marathon Run and 5K Run/Walk is held on Sunday, October 11, 2026, starting at 9:00 AM.

Where does the Chestertown Challenge Half Marathon Run and 5K Run/Walk take place?

It takes place in Chestertown, Maryland.

What distances does the Chestertown Challenge Half Marathon Run and 5K Run/Walk offer?

The half marathon (13.1 miles), plus 3.1 Miles, Silent Hero.

Is the Chestertown Challenge Half Marathon Run and 5K Run/Walk course flat and good for a PR?

The Chestertown Challenge Half Marathon Run and 5K Run/Walk is a rolling hills, loop course course. The course is USATF-certified, so finish times can be used for qualifying.

How many people run the Chestertown Challenge Half Marathon Run and 5K Run/Walk?

HalfRuns has finish records for 646 runners who have completed the Chestertown Challenge Half Marathon Run and 5K Run/Walk.

HalfRuns editorial — independent, no paid placement.

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