Maryland Trail Running Calendar 2025-2026

Header image

Explore the best trail runs in Maryland for 2025-2026! Our updated list features 196 exciting races across the region. Find your next race in Maryland below and join the running community at these great events!

January 2026
Jan
10
Saturday

Chill Chase 10k

5 km 10 km
Jan
31
Saturday

Mid-Maryland Trail Festival 50k

Trail Run 50 km
February 2026
Feb
7
Saturday

The Algonquin 50K

Trail Run 50 km
Feb
14
Saturday

Hot for Chocolate 5K - Saint Leonard

5 km
Feb
14
Saturday

Cupid's Chase Silver Spring

5 km
Feb
14
Saturday

Cupid's Chase Baltimore

5 km
March 2026
Mar
21
Saturday

Hat Run 50K

Trail Run 50 km
Mar
28-29
Sa - Su

Genesee Valley Ultra

Backyard Ultra 6 hr 12 hr 24 hr
Mar
28
Saturday

Colorectal Cancer Awareness 5K

5 km
April 2026
Apr
4
Saturday

RunSBY Events Salisbury Marathon

5 km 13 mi 26 mi
Apr
11
Saturday

Oasis 5K

5 km
Apr
11
Saturday

St Joseph 5K

5 km
Apr
12
Sunday

Breeze Thru the Trees 5k

Trail Run 5 km
Apr
18
Saturday

Run to Remember - Sykesville

Trail Run 5 mi 25 km 50 km 8 hr
Apr
18
Saturday

SMHS Makin' Hay 10K

5 km 10 km
Apr
25
Saturday

C&O Canal 100

Trail Run 100 mi
May 2026
May
2
Saturday

Farm Park Challenge

Trail Run 25 km 3 hr ... 6 hr 10 hr
May
2-3
Sa - Su

Frederick Running Festival

5 km 13 mi
May
2
Saturday

Run For the Kids

5 km
May
2
Saturday

Go Gray in May

5 km
Articles
Top 10 Marathons in the Netherlands — The Ultimate Dutch Marathon Bucket List: 10 Unmissable Races
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