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Trail runs in Isle of Wight

Find trail runs near me in Isle of Wight for 2025/2026 - search by date or place, display on a map or use the advanced search to find your perfect race.

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Click an event for full event details, location, route, sustainability, what's included and how to enter.

Great challenges need great settings, and up to 2,000 adventurers will take on the Isle of Wight stunning coastal path – all out to push themselves further.
  • Sat 3 May
  • £139
  • 13 charities
  • Sat 3 May
  • £139
  • 13 charities
Ventnor, Isle of Wight, UK

Isle of Wight Ultra Challenge | 1st Half

Great challenges need great settings, and up to 2,000 adventurers will take on the Isle of Wight stunning coastal path – all out to push themselves further.

  • Chip timing
  • Enter online
  • GPS tracking
  • Hilly
  • Age 18 & over
  • 52 km trail running + 900 m ascent
Great challenges need great settings, and up to 2,000 adventurers will take on the Isle of Wight stunning coastal path – all out to push themselves further.
  • Sat 3 May
  • £199
  • 13 charities
  • Sat 3 May
  • £199
  • 13 charities
Ventnor, Isle of Wight, UK

Isle of Wight Ultra Challenge | Full Continuous

Great challenges need great settings, and up to 2,000 adventurers will take on the Isle of Wight stunning coastal path – all out to push themselves further.

  • Chip timing
  • Enter online
  • GPS tracking
  • Undulating
  • Hilly
  • Age 18 & over
  • 106 km multi terrain running + 1800 m ascent
The full 106km circumnavigation of the Isle of Wight, in daylight hours. Overnight at Cowes for a well-earned rest on this wonderful exploration of the coastal routes around the island.
  • Sat 3 - Sun 4 May
  • £199
  • 13 charities
  • Sat 3 - Sun 4 May
  • £199
  • 13 charities
Ventnor, Isle of Wight, UK

Isle of Wight Ultra Challenge | Full 2 Day Daylight

The full 106km circumnavigation of the Isle of Wight, in daylight hours. Overnight at Cowes for a well-earned rest on this wonderful exploration of the coastal routes around the island.

  • Chip timing
  • Enter online
  • Undulating
  • Hilly
  • Age 18 & over
  • 106 km multi terrain running + 1960 m ascent
Great challenges need great settings, and up to 2,000 adventurers will take on the Isle of Wight stunning coastal path – all out to push themselves further.
  • Sat 3 - Sun 4 May
  • £169
  • 13 charities
  • Sat 3 - Sun 4 May
  • £169
  • 13 charities
Ventnor, Isle of Wight, UK

Isle of Wight Ultra Challenge | 3/4 Challenge

Great challenges need great settings, and up to 2,000 adventurers will take on the Isle of Wight stunning coastal path – all out to push themselves further.

  • Enter online
  • Undulating
  • Hilly
  • Age 18 & over
  • 82 km trail running + 1300 m ascent
Great challenges need great settings, and up to 2,000 adventurers will take on the Isle of Wight stunning coastal path – all out to push themselves further.
  • Sat 3 May
  • £139
  • 13 charities
  • Sat 3 May
  • £139
  • 13 charities
Ventnor, Isle of Wight, UK

Isle of Wight Ultra Challenge | Southern 50

Great challenges need great settings, and up to 2,000 adventurers will take on the Isle of Wight stunning coastal path – all out to push themselves further.

  • Chip timing
  • Enter online
  • Undulating
  • Hilly
  • Age 18 & over
  • 50 km trail running + 1025 m ascent
Great challenges need great settings, and up to 2,000 adventurers will take on the Isle of Wight stunning coastal path – all out to push themselves further.
  • Sat 3 May
  • £89
  • 13 charities
  • Sat 3 May
  • £89
  • 13 charities
Ventnor, Isle of Wight, UK

Isle of Wight Ultra Challenge | 1st Quarter

Great challenges need great settings, and up to 2,000 adventurers will take on the Isle of Wight stunning coastal path – all out to push themselves further.

  • Chip timing
  • Enter online
  • GPS tracking
  • Undulating
  • Age 14 & over
  • 25 km trail running + 500 m ascent
Great challenges need great settings, and up to 2,000 adventurers will take on the Isle of Wight stunning coastal path – all out to push themselves further.
  • Sat 3 May
  • £139
  • 13 charities
  • Sat 3 May
  • £139
  • 13 charities
Cowes, Isle of Wight, UK

Isle of Wight Ultra Challenge | 2nd Half

Great challenges need great settings, and up to 2,000 adventurers will take on the Isle of Wight stunning coastal path – all out to push themselves further.

  • Chip timing
  • Enter online
  • GPS tracking
  • Undulating
  • Hilly
  • Age 18 & over
  • 54 km trail running + 1000 m ascent
Start at the showground basecamp and follow the trails around the estuary, cross on the chain ferry and get a good feel for Cowes and its surrounding area.
  • Sat 3 May
  • £39
  • 13 charities
  • Sat 3 May
  • £39
  • 13 charities
Ventnor, Isle of Wight, UK

Medina 10 Mile

Start at the showground basecamp and follow the trails around the estuary, cross on the chain ferry and get a good feel for Cowes and its surrounding area.

  • Enter online
  • Flat
  • Age 8 & over
  • 10 miles trail running
Great challenges need great settings, and up to 2,000 adventurers will take on the Isle of Wight stunning coastal path – all out to push themselves further.
  • Sun 4 May
  • £89
  • 13 charities
  • Sun 4 May
  • £89
  • 13 charities
Sandown, Isle of Wight, UK

Isle of Wight Ultra Challenge | 4th Quarter

Great challenges need great settings, and up to 2,000 adventurers will take on the Isle of Wight stunning coastal path – all out to push themselves further.

  • Chip timing
  • Enter online
  • GPS tracking
  • Undulating
  • Age 14 & over
  • 25 km trail running + 500 m ascent

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