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

March 2026
Mar
14
Saturday

Centurion Hundred Hills 50km

Trail Run 50 km
Mar
28
Saturday

Run the Wild Half Marathon - Spring Edition

Trail Run 21 km
April 2026
Apr
6
Monday

Mortimer 10km

Trail Run 10 km
Apr
11
Saturday

Henley River Half Marathon

Trail Run 10 km 13 mi
Apr
18
Saturday

Windsor 50 Ultra Challenge

Trail Run 10 km 25 km 50 km
Apr
18
Saturday

Chiltern Ridge Classic 50k

Trail Run 50 km
Apr
18
Saturday

Spring Trail Series by Ultra X

Trail Run 12 km 25 km ... 50 mi 110 km
May 2026
May
2
Saturday

Centurion Thames Path 100

Trail Run 100 mi
May
3
Sunday

Rapid Relays

Trail Run 5 km 10 km
May
9
Saturday

Chiltern Hills 100K

Trail Run 100 km
May
16
Saturday

Centurion North Downs Way 50

Trail Run 50 mi
May
17
Sunday

Reigate Priory Park 10K Charity Fun Run

Trail Run 10 km
May
30
Saturday

Beat the Sunset 50km

Trail Run 50 km
May
30
Saturday

The Ridgeway Challenge

Trail Run 139 km
June 2026
Jun
28
Sunday

Marlow Trail Run

Trail Run 5 km 10 km 13 mi
July 2026
Jul
26
Sunday

Maidenhead Trail Run

Trail Run 5 km 10 km 13 mi
September 2026
Sep
5
Saturday

Henley River Half Marathon

Trail Run 10 km 13 mi
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