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

March 2026
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 21 km
Apr
18
Saturday

Windsor 50 Ultra Challenge

Trail Run 10 km 25 km 50 km
Apr
18
Saturday

Chiltern Ridge Classic 50k

Trail Run 51 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
3
Sunday

Box Hill Vertical KM

Trail Run 13 mi
May
9
Saturday

Chiltern Hills 100K

Trail Run 100 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
17
Sunday

Reigate Priory Park 10K Charity Fun Run

Trail Run 10 km
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
May
30
Saturday

The Ridgeway Challenge

Trail Run 139 km
June 2026
Jun
3
Wednesday

Surrey Hills Half Marathon

Trail Run 13 mi
Jun
20
Saturday

Beyond Trails London

Trail Run 26 km 55 km
Jun
20-21
Sa - Su

Centaur 100 Mile Ultra

Trail Run 21 km 42 km ... 100 mi 24 hr
Jun
20
Saturday

Phoenix - Denbies Marathon & Half Marathon

Trail Run 21 km 42 km
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