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Trail Running Calendar near Osterville 2025-2026

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

October 2025
Oct
5
Sunday

Nicole Podkowa 5K

5 km
Oct
11-12
Sa - Su

Cape Cod Marathon Weekend

5 km 13 mi 26 mi
Oct
12
Sunday

Nantucket Half Marathon

6 mi 13 mi
February 2026
Feb
14
Saturday

MV Winter Classic 20 Miler

10 mi 20 mi
March 2026
Mar
1
Sunday

Hyannis Marathon

10 km 13 mi 26 mi
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