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Trail runs in Isle of Wight in May 2025

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

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The first half of the Isle of Wight circuit explore 52km of scenic coastal trails, enjoy spectacular coastal views along the undulating route with plenty of rest stops to keep you well fuelled.
  • Sat 3 May 2025
  • 12 charities
  • Sat 3 May 2025
  • 12 charities
Ventnor, Isle of Wight, UK

Isle of Wight Ultra Challenge | 1st Half charity places

The first half of the Isle of Wight circuit explore 52km of scenic coastal trails, enjoy spectacular coastal views along the undulating route with plenty of rest stops to keep you well fuelled.

  • Chip timing
  • Enter online
  • GPS tracking
  • Hilly
  • Age 18 & over
  • 52 km trail running + 1100 m ascent
An epic challenge, making a full 106km circuit of the Isle of Wight, starting and finishing in Chale, enjoy well stocked rest stops and superb scenery every step of the way.
  • Sat 3 May 2025
  • 12 charities
  • Sat 3 May 2025
  • 12 charities
Ventnor, Isle of Wight, UK

Isle of Wight Ultra Challenge | Full continuous charity places

An epic challenge, making a full 106km circuit of the Isle of Wight, starting and finishing in Chale, enjoy well stocked rest stops and superb scenery every step of the way.

  • Chip timing
  • Enter online
  • GPS tracking
  • Undulating
  • Hilly
  • Age 18 & over
  • 106 km multi terrain running + 1960 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 2025
  • 12 charities
  • Sat 3 - Sun 4 May 2025
  • 12 charities
Ventnor, Isle of Wight, UK

Isle of Wight Ultra Challenge | Full 2 day daylight charity places

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
The route is 3/4 of the Full Challenge – so starts at the Chale basecamp, heads around the fantastic southern section – on to Cowes, and then a final quarter to a finish line at Culver Down.
  • Sat 3 - Sun 4 May 2025
  • 12 charities
  • Sat 3 - Sun 4 May 2025
  • 12 charities
Ventnor, Isle of Wight, UK

Isle of Wight Ultra Challenge | 3/4 Challenge charity places

The route is 3/4 of the Full Challenge – so starts at the Chale basecamp, heads around the fantastic southern section – on to Cowes, and then a final quarter to a finish line at Culver Down.

  • Chip timing
  • Enter online
  • Undulating
  • Hilly
  • Age 18 & over
  • 82 km trail running
A NEW looped route setting out from the Chale basecamp, that gives you the best of the Island’s dramatic scenery along famous southern coastline to the iconic ‘Needles’.
  • Sat 3 May 2025
  • 12 charities
  • Sat 3 May 2025
  • 12 charities
Ventnor, Isle of Wight, UK

Isle of Wight Ultra Challenge | Southern Loop charity places

A NEW looped route setting out from the Chale basecamp, that gives you the best of the Island’s dramatic scenery along famous southern coastline to the iconic ‘Needles’.

  • Chip timing
  • Enter online
  • Undulating
  • Hilly
  • Age 18 & over
  • 50 km trail running
Take on a 25km challenge along the trails of the southern coast of the Isle of Wight, finishing by The Needles for a BBQ lunch.
  • Sat 3 May 2025
  • 12 charities
  • Sat 3 May 2025
  • 12 charities
Ventnor, Isle of Wight, UK

Isle of Wight Ultra Challenge | 1st Quarter charity places

Take on a 25km challenge along the trails of the southern coast of the Isle of Wight, finishing by The Needles for a BBQ lunch.

  • Chip timing
  • Enter online
  • GPS tracking
  • Undulating
  • Age 14 & over
  • 25 km trail running + 660 m ascent
Starting in Cowes, follow a clockwise route along the eastern side of the Isle of Wight, enjoying superb coastal views en route to the finish line at Chale.
  • Sat 3 May 2025
  • 12 charities
  • Sat 3 May 2025
  • 12 charities
Cowes, Isle of Wight, UK

Isle of Wight Ultra Challenge | 2nd Half charity places

Starting in Cowes, follow a clockwise route along the eastern side of the Isle of Wight, enjoying superb coastal views en route to the finish line at Chale.

  • Enter online
  • Undulating
  • Hilly
  • Age 18 & over
  • 54 km trail running + 980 m ascent
Starting at our showground basecamp – you’ll follow the trails around the estuary, cross on the chain ferry – and really get a good feel for Cowes and its surrounding area.
  • Sat 3 May 2025
  • 12 charities
  • Sat 3 May 2025
  • 12 charities
Ventnor, Isle of Wight, UK

Medina 10 Mile charity places

Starting at our showground basecamp – you’ll follow the trails around the estuary, cross on the chain ferry – and really get a good feel for Cowes and its surrounding area.

  • Chip timing
  • Enter online
  • Flat
  • Undulating
  • Age 8 & over
  • 10 miles trail running
Pass through Sandown, Shanklin and Ventnor before finishing at the basecamp in Chale for a celebratory hot meal awaits with your medal.
  • Sun 4 May 2025
  • 12 charities
  • Sun 4 May 2025
  • 12 charities
Sandown, Isle of Wight, UK

Isle of Wight Ultra Challenge | 4th Quarter charity places

Pass through Sandown, Shanklin and Ventnor before finishing at the basecamp in Chale for a celebratory hot meal awaits with your medal.

  • Chip timing
  • Enter online
  • GPS tracking
  • Undulating
  • Age 14 & over
  • 25 km trail running + 480 m ascent

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