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Trail Running Calendar near Saint Leonard 2025-2026

Explore the top trail runs near Saint Leonard for 2025-2026! We've gathered 25 exciting races in the area. Check out our detailed list below to find your next local race.

September 2025
Sep
20
Saturday

Ironman Maryland

Triathlon
Sep
20
Saturday

Hospice of the Chesapeake Blue Crab Fun Run 5K

5 km
Sep
20
Saturday

Munro Hampton Alumni Association DC 5K

5 km
Sep
20
Saturday

St. Charles Running Festival

5 km 10 km
Sep
27-28
Sa - Su

5K Walk-Run Soul Fitness Weekend

5 km
October 2025
Oct
4
Saturday

Friends of the Poor 5K Walk/Run

5 km
Oct
5
Sunday

Metric Marathon

26 km
Oct
12
Sunday

Lighthouse Lookout 10k

5 km 10 km
Oct
12
Sunday

Run the Vineyards - Running Hare 5K

5 km
Oct
12
Sunday

Bivalves for Boobies 5K

5 km
Oct
18
Saturday

Beach to Beer 10K

5 km 10 km
Oct
18
Saturday

Autumn Adventure 10k

5 km 10 km
Oct
25
Saturday

North Point Fright Night 5K & Haunted Trail

Trail Run 5 km
November 2025
Nov
2
Sunday

We Got Your Six Running Festival

10 km 21 km 42 km
Nov
8
Saturday

Rosaryville Veterans Day Trail Race

Trail Run 20 km 50 km
Nov
8
Saturday

Historic Drawbridge Running Festival

5 km 21 km 42 km
Nov
22
Saturday

Budds Creek Turkey Trot Half

5 km 10 km 21 km
Nov
22
Saturday

Indian Head Turkey Trot 10k

5 km 10 km
Nov
27
Thursday

Turkey Trot - Saint Leonard

5 km
December 2025
Dec
6
Saturday

Jingle Bell Run - Dowell

5 km
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