Sun, Oct 11, 2026

Chestertown Challenge Half Marathon Run and 5K Run/Walk

Chestertown, MD

Registration openAnnual since at least 2015

Half Marathon5K

Entry is $25 now and rises to $30 after Sep 20, 2026, so registering before then saves $5.

About the Chestertown Challenge Half Marathon Run and 5K Run/Walk

The course starts and finishes at Wilmer Park and runs entirely on paved country roads through the surrounding area. The terrain rolls gently throughout, nothing steep or technical, just the kind of quiet rural road running that lets you settle into a rhythm. Police control the roads, and there are markers and directional arrows along the way to keep you on course.

Packet pickup and race-day registration both happen at Wilmer Park on the morning of the race, so there is no separate trip the day before. Food and refreshments are available at the finish, and restrooms are set up at the start and at points along the half marathon course.

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Finish-Time Stats

Going by the 2025 results, this is a small, friendly field, with a competitive front end and a big recreational middle.

13.1 Miles · 2025 results

67finishers

1:23:31winner

2:07:56median

3:05:20cutoff

Top 3: Jack Elvin (1:23:31) · Michael DePolo (1:30:39) · Pascal Patterson (1:30:42)

3.1 Miles · 2025 results

42finishers

19:18winner

34:04median

54:50cutoff

Top 3: Lisa Victorius (19:18) · Anye Forti (21:13) · Anonymous Anonymous (21:24)

The Chestertown Challenge Half Marathon Run and 5K Run/Walk has been held every year since at least 2015. That is as far back as RunSignup's records for this race go, so it may well be older.

Where Would You Finish?

Enter a finish time to see where it lands against the most recent 13.1 Miles results.

Median

See how your time stacks up nationally →

How we calculate these stats: RunSesh calculates these figures from the most recent published results of past editions, sourced from RunSignup. We show aggregates only: field size, winning and median times, and the cutoff. We never publish individual finisher tables. Last updated Jul 27, 2026.

Distances & Start Times

13.1 Miles10/11/2026 09:00$50

3.1 Miles10/11/2026 09:00$25

Silent Hero10/11/2026 09:00$30

Going for a Time?

Set a goal and get a pace band: every mile split on a card sized for your phone lock screen, so race morning needs no math.

Plan Your Trip

Where to Stay

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Common Questions About the Chestertown Challenge Half Marathon Run and 5K Run/Walk

Will I finish last at the Chestertown Challenge Half Marathon Run and 5K Run/Walk?

Almost certainly not. Half the 13.1 Miles field finished slower than 2:07:56, and the last recorded finisher came in around 3:05:20, so there is a long tail of runners behind the middle of the pack. Most fields are far slower than people expect.

Is the Chestertown Challenge Half Marathon Run and 5K Run/Walk a good first 13.1 Miles?

It is a small race (67 finishers), which is friendlier and less intimidating than a big-city event, though the field thins out. There is no qualifying time, and the finish-time spread above shows how varied the field really is. If it is your first 13.1 Miles, that spread matters more than the winner's time.

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

The 13.1 Miles winner ran 1:23:31 while the median finisher took 2:07:56. That spread points to a mixed field, with a competitive front and a big recreational middle.