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Trail Running Calendar near Upper Woolhampton 2025-2026

Explore the top trail runs near Upper Woolhampton for 2025-2026! We've gathered 77 exciting races in the area. Check out our detailed list below to find your next local race.

April 2026
Apr
26
Sunday

The Drop - Winchester

Trail Run 10 mi 15 mi
May 2026
May
3
Sunday

Rapid Relays

Trail Run 5 km 10 km
May
4
Monday

BigWayRound - Winchester

Trail Run 14 mi 19 mi 42 km 50 km
May
4
Monday

Harewood Forest Trail Race

Trail Run 5 km 10 km
May
9
Saturday

Collingbourne Races

Trail Run 10 km 21 km
May
9-10
Sa - Su

Goring Gap Trails

Trail Run 33 mi 50 mi
May
16
Saturday

Centurion North Downs Way 50

Trail Run 50 mi
May
23
Saturday

The Fox Trail

Trail Run 20 km 41 km 62 km
May
30
Saturday

Beat the Sunset 50km

Trail Run 50 km
June 2026
Jun
13
Saturday

Centurion South Downs Way 100

Trail Run 100 mi
Jun
13
Saturday

Centurion South Downs Way 50km

Trail Run 50 km
Jun
28
Sunday

Marlow Trail Run

Trail Run 5 km 10 km 21 km
July 2026
Jul
19
Sunday

BigHeat Trails (FIRE)

Trail Run 16 mi 42 km
Jul
26
Sunday

Maidenhead Trail Run

Trail Run 5 km 10 km 21 km
August 2026
Aug
1
Saturday

North Downs 50 Ultra Challenge

Trail Run 10 km 24 km 25 km 50 km
September 2026
Sep
5
Saturday

Henley River Half Marathon

Trail Run 10 km 21 km
November 2026
Nov
8
Sunday

Windsor Trail Run

Trail Run 10 km 21 km
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