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Trail runs in South East in May 2025

Find trail runs near me in South East 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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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
Scenic mixed-terrain route around Bewl Water on undulating rural wooded trails and quiet country lanes. The marathon on the same day was previously rated one of the top UK marathons.
  • Sat 10 May
  • £58-£60
  • Sat 10 May
  • £58-£60
Wadhurst, East Sussex, UK

Bewl Water Spring | Ultra

Scenic mixed-terrain route around Bewl Water on undulating rural wooded trails and quiet country lanes. The marathon on the same day was previously rated one of the top UK marathons.

  • Chip timing
  • Enter online
  • Hilly
  • Age 18 & over
  • 50 km trail running
Previously rated one of the top UK marathons! Scenic mixed-terrain route around Bewl Water on undulating rural wooded trails and quiet country lanes.
  • Sat 10 May
  • £53-£55
  • Sat 10 May
  • £53-£55
Wadhurst, East Sussex, UK

Bewl Water Spring | Marathon

Previously rated one of the top UK marathons! Scenic mixed-terrain route around Bewl Water on undulating rural wooded trails and quiet country lanes.

  • Chip timing
  • Enter online
  • Hilly
  • Age 18 & over
  • 26.2 miles trail running
Scenic mixed-terrain route around Bewl Water on undulating rural wooded trails and quiet country lanes. The marathon on the same day was previously rated one of the top UK marathons.
  • Sat 10 May
  • £43-£45
  • Sat 10 May
  • £43-£45
Wadhurst, East Sussex, UK

Bewl Water Spring | Half Marathon

Scenic mixed-terrain route around Bewl Water on undulating rural wooded trails and quiet country lanes. The marathon on the same day was previously rated one of the top UK marathons.

  • Chip timing
  • Enter online
  • Hilly
  • Age 17 & over
  • 13.1 miles trail running
Scenic mixed-terrain route around Bewl Water on undulating rural wooded trails and quiet country lanes. The marathon on the same day was previously rated one of the top UK marathons.
  • Sat 10 May
  • £30-£32
  • Sat 10 May
  • £30-£32
Wadhurst, East Sussex, UK

Bewl Water Spring | 10K

Scenic mixed-terrain route around Bewl Water on undulating rural wooded trails and quiet country lanes. The marathon on the same day was previously rated one of the top UK marathons.

  • Chip timing
  • Enter online
  • Undulating
  • Age 16-80
  • 10 km trail running
From Turners Hill the route heads south through wonderful Sussex countryside, then up and over the testing South Downs before the coast comes into view and the final few km to the Racecourse finish!
  • Sat 24 - Sun 25 May
  • £139
  • 12 charities
  • Sat 24 - Sun 25 May
  • £139
  • 12 charities
Crawley, West Sussex, UK

Sussex Marathon

From Turners Hill the route heads south through wonderful Sussex countryside, then up and over the testing South Downs before the coast comes into view and the final few km to the Racecourse finish!

  • Chip timing
  • Enter online
  • GPS tracking
  • Undulating
  • Age 18 & over
  • 42 km trail running + 700 m ascent
A new 25km option – ideal if you want to explore the surrounding countryside around Brighton and sections of the South Downs Way with its fabulous views back over the Sussex countryside.
  • Sun 25 May
  • £89
  • 14 charities
  • Sun 25 May
  • £89
  • 14 charities
Brighton, East Sussex, UK

Brighton Challenge

A new 25km option – ideal if you want to explore the surrounding countryside around Brighton and sections of the South Downs Way with its fabulous views back over the Sussex countryside.

  • Enter online
  • Undulating
  • Hilly
  • Age 14 & over
  • 25 km trail running + 400 m ascent
Cancelled
A new and unique concept where you turn up ready to conquer a Half Marathon but if you're feeling great tackle a Marathon, or go easy and run a cool 10km depending on how you feel on the day!
  • Sat 31 May
  • £52
  • Cancelled
  • Sat 31 May
  • £52
  • Cancelled
Gerrards Cross, Buckinghamshire, UK

Running Tribe Races | May | 32K

A new and unique concept where you turn up ready to conquer a Half Marathon but if you're feeling great tackle a Marathon, or go easy and run a cool 10km depending on how you feel on the day!

  • Enter online
  • Undulating
  • Age 17 & over
  • 32 km multi terrain running
  • Fri 2 May
Egham, Surrey, UK

Midweek Chasing Numbers May

  • 7 hrs trail running
  • Sun 4 May
Lancing, West Sussex, UK

Three Forts Challenge | 5 Mile Trail Run

  • 5 miles trail running
  • Sun 4 May
Camberley, Surrey, UK

Run Frimley | Fun Run

  • 1 km trail running
  • Mon 5 May
Winchester, Hampshire, UK

BigWayRound - Winchester | 14 Mile

  • 14 miles trail running
  • Mon 5 May
Winchester, Hampshire, UK

BigWayRound - Winchester | 19 Mile

  • 19 miles trail running
  • Mon 5 May
Winchester, Hampshire, UK

BigWayRound - Winchester | Marathon

  • 26.2 miles trail running
  • Mon 5 May
Winchester, Hampshire, UK

BigWayRound - Winchester | 50K Ultra Marathon

  • 50 km trail running
  • Mon 5 May
Staines, Surrey, UK

Bank Holiday Madness May

  • 7 hrs trail running
  • Mon 5 May
Andover, Hampshire, UK

Harewood Forest Trail Race | 10K CaniCross

  • 10 km trail running

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