Chesapeake City close

Trail Running Calendar near Chesapeake City 2025-2026

Explore the top trail runs near Chesapeake City for 2025-2026! We've gathered 58 exciting races in the area. Check out our detailed list below to find your next local race.

September 2025
Sep
28
Sunday

Faithful Friends 5K

5 km
Sep
28
Sunday

Bear Trail Half Marathon

Trail Run 10 km 13 mi
October 2025
Oct
4
Saturday

Half Marathon at Cedar Lane Regional Park

5 km 10 km 15 km 13 mi
Oct
11
Saturday

Delaware School for the Deaf 5k Run/Walk

5 km
Oct
17
Friday

Screech's Night Owl 5K

5 km
Oct
18
Saturday

Delaware Trail Fest

Trail Run 12 km 24 km 12 hr
Oct
18
Saturday

Superhero for Hope Run/Walk 5K

5 km
Oct
19
Sunday

Delaware Distance Classic 15K

5 km 15 km
November 2025
Nov
1
Saturday

Delaware School for the Deaf 5k Run/Walk

5 km
Nov
8
Saturday

Mushroom Cap Half Marathon

5 mi 13 mi
Nov
9
Sunday

Beds4Vets Veterans Day 5K

5 km
Nov
22
Saturday

CRCQL X Swat Environmental Justice 5k

5 km
Nov
22
Saturday

New Garden Gobbler

2 mi 5 km
Nov
27
Thursday

Bulle Rock Turkey Trot 5K

5 km
Nov
28
Friday

#OptOutside Black Friday Fun Run

5 km
December 2025
Dec
6
Saturday

Half Marathon at Cedar Lane Regional Park

13 mi
Dec
14
Sunday

Holiday Hustle 5K - Bel Air

5 km
April 2026
Apr
19
Sunday

Delaware Running Festival

5 km 10 km 13 mi 26 mi
Articles
The Beauty of the Easy Run — Why slowing down might be the smartest thing you do for your running
Mizuno Wave Rider 28: Elevating the Legacy of a Running Icon
Garmin Forerunner Review: Garmin Forerunner Series
Stride with Confidence: A Comprehensive Guide to Saucony Running Shoes