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Trail Running Calendar near Maidenhead 2025-2026

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Explore the top trail runs near Maidenhead for 2025-2026! We've gathered 131 exciting races in the area. Check out our detailed list below to find your next local race.

September 2026
Sep
26
Saturday

Chiltern 50 Ultra Challenge

Trail Run 10 km 25 km 50 km
October 2026
Oct
3
Saturday

London Epping Forest 50 Km

Trail Run 50 km
Oct
4
Sunday

Bolt Round The Holt

Trail Run 5 km 10 km Half Marathon
Oct
10
Saturday

North Downs Way Ultra Run

Trail Run 30 mi
Oct
11
Sunday

Frieth Hilly 5km & 10km

Trail Run 5 km 10 km
Oct
17
Saturday

Centurion Autumn 100

Trail Run 100 mi
Oct
24
Saturday

Thames Trail Ultra

Trail Run 47 mi
November 2026
Nov
8
Sunday

Windsor Trail Run Half Marathon

Trail Run 10 km Half Marathon
Nov
24
Tuesday

Devils Punchbowl 10km

Trail Run 10 km
Nov
29
Sunday

Serpent Trail Ultra Run

Trail Run 30 mi
December 2026
Dec
5
Saturday

Box Hill Vertical KM

Trail Run 13 mi
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