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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 23 exciting races in the area. Check out our detailed list below to find your next local race.

September 2025
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 Half Marathon Marathon
Nov
8
Saturday

Rosaryville Veterans Day Trail Race

Trail Run 20 km 50 km
Nov
8
Saturday

Historic Drawbridge Running Festival

5 km Half Marathon Marathon
Nov
22
Saturday

Budds Creek Turkey Trot Half

5 km 10 km Half Marathon
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
Dec
14
Sunday

Krampus Krawl at Maryland International Raceway 10k

5 km 10 km
February 2026
Feb
14
Saturday

Hot for Chocolate 5K - Saint Leonard

5 km
Feb
22
Sunday

Rosaryville Ramble Half

5 km 10 km Half Marathon
March 2026
Mar
22
Sunday

Cedarville Charge 10k

5 km 10 km
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