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Trail Running Calendar near Isle of Wight 2026-2027

Monthly updates for Isle of Wight

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

Explore the top trail runs near Isle of Wight for 2026-2027! We've gathered 54 exciting races in the area. Check out our detailed list below to find your next local race.

March 2026
Mar
21
Sa

Stansted House Trail Run

Trail Run 10 km 16 km Half Marathon
Mar
28
Sa

Intergalactic

Trail Run 3 mi
April 2026
Apr
6
Mo

West Wight 3 Hills

Trail Run 8 mi
Apr
26
Su

The Drop - Winchester

Trail Run 10 mi 15 mi
May 2026
May
2-3
Sa - Su

Isle of Wight Ultra Challenge

Trail Run 10 mi 25 km ... 82 km 106 km
May
4
Mo

BigWayRound - Winchester

Trail Run 14 mi 19 mi 26 mi 50 km
May
31
Su

Southampton Running Festival

Trail Run 5 km 10 km Half Marathon
June 2026
Jun
7
Su

BigSea Trails (WATER)

Trail Run 13 mi 18 mi 26 mi 54 km
Jun
7
Su

Bournemouth Beach Race

Trail Run 5 km 10 km
Jun
13
Sa

Centurion South Downs Way 100

Trail Run 100 mi
Jun
13
Sa

Centurion South Downs Way 50km

Trail Run 50 km
Jun
13
Sa

The Maverick Dorset Trail

Trail Run 7 km 13 km 23 km
Jun
20
Sa

Race To The King

Trail Run 30 km 50 km 80 km 100 km
Jun
28
Su

The Hangers Way 50K

Trail Run 50 km
July 2026
Jul
4
Sa

Serpent Trail

Trail Run 10 km 20 km ... 75 km 100 km
Jul
26
Su

RunThrough Trails South Downs

Trail Run 12 km 25 km 50 km
August 2026
Aug
16
Su

Southampton Running Festival

Trail Run 5 km 10 km Half Marathon
Aug
23
Su

The Big Pilgrimage

Trail Run 15 mi 26 mi
September 2026
Sep
5
Sa

Jurassic Coast Ultra Run

Trail Run 30 mi
Sep
12-13
Sa - Su

Isle Of Wight Fell Race Series

Trail Run 4 km 12 km Half Marathon