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

Walk, jog or run the stunning coastal paths of the Isle of Wight for a great charity cause, from the base camp at Chale, visiting historic Cowes and the iconic Needles en route.
  • Sat 3 - Sun 4 May 2025
  • £10-£40
  • 5 charities
  • Sat 3 - Sun 4 May 2025
  • £10-£40
  • 5 charities
Ventnor, Isle of Wight, UK

Isle of Wight Ultra Challenge

Walk, jog or run the stunning coastal paths of the Isle of Wight for a great charity cause, from the base camp at Chale, visiting historic Cowes and the iconic Needles en route.

  • Newcomers
  • Entertainment
  • Music
  • Chip timing
  • Enter online
  • GPS tracking
  • Fundraising required
  • Undulating
  • Event village
  • Age 14 & over
  • 1 day 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 2025
  • £58-£60
  • Sat 10 May 2025
  • £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
An ultra run to the south coast with top reviews, amazing scenery, wonderful trails and rolling downs before reaching the promenade finish line for your ice cream and medal!
  • Sat 10 May 2025
  • £68-£70
  • Sat 10 May 2025
  • £68-£70
Horsham, West Sussex, UK

Run to the Sea Brighton

An ultra run to the south coast with top reviews, amazing scenery, wonderful trails and rolling downs before reaching the promenade finish line for your ice cream and medal!

  • Newcomers
  • Chip timing
  • Enter online
  • Hilly
  • Event village
  • Age 20 & over
  • 50 km multi terrain 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 2025
  • £53-£55
  • Sat 10 May 2025
  • £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 2025
  • £43-£45
  • Sat 10 May 2025
  • £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 2025
  • £30-£32
  • Sat 10 May 2025
  • £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
Walk, jog or run along the capital to coast route for charity, with a range of distance options available and superb support all the way, for all abilities and experience levels.
  • Sat 24 - Sun 25 May 2025
  • £10-£40
  • 8 charities
  • Sat 24 - Sun 25 May 2025
  • £10-£40
  • 8 charities
Brighton, East Sussex, UK

London 2 Brighton Ultra Challenge

Walk, jog or run along the capital to coast route for charity, with a range of distance options available and superb support all the way, for all abilities and experience levels.

  • Entertainment
  • Chip timing
  • Enter online
  • GPS tracking
  • Fundraising required
  • Undulating
  • Event village
  • Age 14 & over
  • 1 day trail running
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 2025
  • £52
  • Sat 31 May 2025
  • £52
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
  • Sun 25 May 2025
Buckingham, Buckinghamshire, UK

Trust 10K Run

  • 10 km trail running

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