Maryland Trail Running Calendar 2025-2026

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Explore the best trail runs in Maryland for 2025-2026! Our updated list features 197 exciting races across the region. Find your next race in Maryland below and join the running community at these great events!

May 2026
May
2
Saturday

Go Gray in May

5 km
May
9
Saturday

Deer Dash 5K

5 km
May
9
Saturday

The Bettie Jane Cancer Foundation 5K Run/Walk

5 km
May
9
Saturday

Tiki Trot 5K

5 km
May
9
Saturday

Savage Race - Maryland Spring

Obstacle Run 3 mi 7 mi
May
25
Monday

Panda 5K

5 km
May
30
Saturday

The More Miles Last One Standing Challenge

Backyard Ultra 4 mi
June 2026
Jun
6
Saturday

Baltimore 10 Miler

10 mi
Jun
6
Saturday

Healthy Tilghman 5k Run/Walk

5 km
Jun
7
Sunday

Cal Tri DC

Triathlon
Jun
14
Sunday

Ironman 70.3 Eagleman

Triathlon
Jun
28
Sunday

MedStar Health Baltimore Women's Classic 5K

5 km
July 2026
Jul
5
Sunday

ASICS Independence Day 4-Miler

4 mi
Jul
11
Saturday

Moonlight 5K

5 km
September 2026
Sep
5
Saturday

Savage Race - Maryland Fall

Obstacle Run 3 mi 7 mi
October 2026
Oct
17
Saturday

Spook Hill Cider & Wine Run

3 mi 4 mi
December 2026
Dec
13
Sunday

Charm City Run Events Signature Races

5 km 4 mi ... 12 mi 20 mi
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