Maidenhead close

Trail Running Calendar near Maidenhead 2025-2026

Header image

Explore the top trail runs near Maidenhead for 2025-2026! We've gathered 129 exciting races in the area. Check out our detailed list below to find your next local race.

December 2025
Dec
24
Wednesday

Winter Woolly 10km

Trail Run 10 km
January 2026
Jan
1
Thursday

Knacker Cracker

Trail Run
Jan
9
Friday

Dark Skies Surrey Hills

Trail Run 5 km 10 km 10 mi
Jan
10
Saturday

Country to Capital Ultra Marathon

Trail Run 43 mi
February 2026
Feb
7-8
Sa - Su

Pilgrim Challenge

Trail Run 66 mi
March 2026
Mar
8
Sunday

Leith Hill Half Marathon

Trail Run 13 mi
Mar
14
Saturday

Humanity Direct Amersham Ultra

Trail Run 10 km 25 km 50 km
Mar
14
Saturday

Centurion Hundred Hills 50km

Trail Run 50 km
April 2026
Apr
18
Saturday

Windsor 50 Ultra Challenge

Trail Run 10 km 25 km 50 km
Articles
The Beauty of the Easy Run — Why slowing down might be the smartest thing you do for your running
Mizuno Wave Rider 28: Elevating the Legacy of a Running Icon
Garmin Forerunner Review: Garmin Forerunner Series
Stride with Confidence: A Comprehensive Guide to Saucony Running Shoes