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Trail Running Calendar near Winchester 2025-2026

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Monthly updates for Winchester

Get new running races (and updates) in your inbox every month.

Explore the top trail runs near Winchester for 2025-2026! We've gathered 69 exciting races in the area. Check out our detailed list below to find your next local race.

December 2025
Dec
21
Su

The Soup Run

Trail Run 6 mi
Dec
24
We

Santa Claws 10km

Trail Run 10 km
Dec
26
Fr

WIM Boxing Day Canter

Trail Run 1 hr
Dec
28
Su

Winter X

Trail Run 10 km 30 km 50 km 70 km
Dec
31
We

MLS Long Valley North - The Nick Bateson Trophy (Long O)

Trail Run 3 km 4 km ... 9 km 12 km
January 2026
Jan
11
Su

Winchester Trail Run

Trail Run 12 km Half Marathon
Jan
11
Su

Winter Hot Chocolate Series

Trail Run 5 mi
Jan
11
Su

Kings Garn Gutter

Trail Run 3 km 4 km ... 6 km 10 km
Jan
17
Sa

The Maverick New Forest Gravel

Trail Run 6 km 12 km 22 km
Jan
18
Su

South Downs & Arundel Winter Trails

Trail Run 15 mi Marathon
Jan
18
Su

Cross Country Series - Ryde

Trail Run 7 km 10 km
Jan
25
Su

The Stonehenge Stomp

Trail Run 5 km 10 km ... 30 km 40 km
Jan
25
Su

Moors Valley Wildwood Half Marathon Trail

Trail Run 10 km Half Marathon
Jan
31
Sa

Queen Elizabeth Country Park Trail Run (QECP)

Trail Run 8 km 15 km 22 km
Jan
31
Sa

Starburster

Trail Run 5 mi 10 mi
February 2026
Feb
3
Tu

Devils Punchbowl 10km

Trail Run 10 km
Feb
7-8
Sa - Su

Pilgrim Challenge

Trail Run 66 mi
Feb
7
Sa

Hibernal Hills 50 Miles

Trail Run 20 mi 50 km 50 mi
Feb
7-8
Sa - Su

Portsmouth/Langstone Coastal Half Marathon

Trail Run 13 mi
Feb
22
Su

BigMud Trails (EARTH)

Trail Run 16 mi Marathon 50 km