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Trail Running Calendar near Chesapeake Beach 2025-2026

Explore the top trail runs near Chesapeake Beach for 2025-2026! We've gathered 62 exciting races in the area. Check out our detailed list below to find your next local race.

May 2025
May
18
Sunday

Capitol Hill Classic 10K

3 km 10 km
May
18
Sunday

Shore Elite PT x Morgan's Message 5k

5 km
May
24
Saturday

4UBen 5k

5 km
June 2025
Jun
4
Wednesday

Global Running Day 10k

5 km 10 km
Jun
7
Saturday

Greenbelt Dash 10k

10 km
Jun
8
Sunday

Ironman 70.3 Eagleman

Triathlon
Jun
15
Sunday

Run to the Taproom 5K

5 km
Jun
19
Thursday

You Matter Juneteenth Freedom 5k Run/Walk

5 km
Jun
28
Saturday

Daring the Blaze 5K Run/Walk

5 km
Jun
29
Sunday

PAL Challenge 10k

5 km 10 km
July 2025
Jul
6
Sunday

Fort Washington 10k

5 km 10 km
Jul
18
Friday

Port City Pursuit 10k

5 km 10 km
Jul
19
Saturday

Endless Summer 6-Hour Run

Trail Run 6 hr
August 2025
Aug
2
Saturday

Neon Nights 5K

5 km
Aug
24
Sunday

Lakeside Loop 10k

5 km 10 km
September 2025
Sep
1
Monday

Labor Day 5K Run/Walk

5 km
Sep
6
Saturday

Dashing to Summer's End 10k

5 km 10 km
Sep
6
Saturday

Diggs Run 5k

5 km
Sep
7
Sunday

Mount Vernon Park 10k

5 km 10 km
Sep
12-14
Fr - Su

Annapolis Run for The Light House

5 km 13 mi
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