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Trail Running Calendar near Winchester 2025-2026

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Explore the top trail runs near Winchester for 2025-2026! We've gathered 36 exciting races in the area. Check out our detailed list below to find your next local race.

February 2025
Feb
23
Sunday

The Terminator

Trail Run 12 mi
Feb
23
Sunday

BigMud Trails (EARTH)

Trail Run 16 mi 26 mi
Feb
23
Sunday

Bigmud Meon Valley Marathon & 16 Mile

Trail Run 16 mi 26 mi
March 2025
Mar
2
Sunday

South Downs Way Ultra Run

Trail Run 30 mi
Mar
2
Sunday

Up On The Downs

Trail Run 5 km 10 km 13 mi
Mar
8
Saturday

The Maverick Original Hampshire

Trail Run 5 km 16 km 24 km
Mar
22
Saturday

Guided Run - Petersfield 10k

Trail Run 10 km
Mar
22
Saturday

Winter's End - 50 Mile Ultra & Marathon

Trail Run 26 mi 50 mi
Mar
23
Sunday

Longparish Run

Trail Run 5 km 10 km
Mar
29
Saturday

Stansted House Trail Run

Trail Run 10 km 16 km 21 km
April 2025
Apr
5
Saturday

Testway Ultra

Trail Run 40 mi 50 mi
Apr
5
Saturday

Guided Half Marathon - Winchester

Trail Run 13 mi
Apr
5
Saturday

Cowdray Estate Trail Run Series

Trail Run 5 km 10 km 10 mi
Apr
12
Saturday

Spring Trail Series by Ultra X

Trail Run 25 km 50 km 75 km
Apr
19
Saturday

Running Roulette

Trail Run 5 mi 10 mi 15 mi
Apr
21
Monday

Dog Friendly

Trail Run 10 km
Apr
21
Monday

West Wight 3 Hills

Trail Run 8 mi
Apr
27
Sunday

Angmering Bluebell Trail Run

Trail Run 10 km 10 mi
May 2025
May
5
Monday

Harewood Forest Trail Race

Trail Run 5 km 10 km
May
5
Monday

BigWayRound - Winchester

Trail Run 14 mi 19 mi 26 mi 50 km
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