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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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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
  • £199
  • 13 charities
  • Sat 3 May
  • £199
  • 13 charities
Ventnor, Isle of Wight, UK

Isle of Wight Ultra Challenge | Full Continuous

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
  • £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
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
  • £139
  • 13 charities
  • Sat 3 May
  • £139
  • 13 charities
Ventnor, Isle of Wight, UK

Isle of Wight Ultra Challenge | 1st Half

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
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
  • £169
  • 13 charities
  • Sat 3 - Sun 4 May
  • £169
  • 13 charities
Ventnor, Isle of Wight, UK

Isle of Wight Ultra Challenge | 3/4 Challenge

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
  • £139
  • 13 charities
  • Sat 3 May
  • £139
  • 13 charities
Ventnor, Isle of Wight, UK

Isle of Wight Ultra Challenge | Southern Loop

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
  • £89
  • 13 charities
  • Sat 3 May
  • £89
  • 13 charities
Ventnor, Isle of Wight, UK

Isle of Wight Ultra Challenge | 1st Quarter

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
  • £139
  • 13 charities
  • Sat 3 May
  • £139
  • 13 charities
Cowes, Isle of Wight, UK

Isle of Wight Ultra Challenge | 2nd Half

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
  • £39
  • 13 charities
  • Sat 3 May
  • £39
  • 13 charities
Ventnor, Isle of Wight, UK

Medina 10 Mile

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
  • £89
  • 13 charities
  • Sun 4 May
  • £89
  • 13 charities
Sandown, Isle of Wight, UK

Isle of Wight Ultra Challenge | 4th Quarter

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
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
The second half distance option of the London to Brighton Challenge starts from Turners Hill, crossing the South Downs National Park before arriving at Brighton.
  • Sat 24 - Sun 25 May
  • £139
  • 12 charities
  • Sat 24 - Sun 25 May
  • £139
  • 12 charities
Crawley, West Sussex, UK

Sussex Marathon

The second half distance option of the London to Brighton Challenge starts from Turners Hill, crossing the South Downs National Park before arriving at Brighton.

  • Chip timing
  • Enter online
  • GPS tracking
  • Undulating
  • Age 18 & over
  • 42 km trail running + 700 m ascent
A great challenge through the Surrey & Sussex countryside – with a Sutton start and Turners Hill / Tulley’s Farm finish.
  • Sat 24 - Sun 25 May
  • £89
  • 14 charities
  • Sat 24 - Sun 25 May
  • £89
  • 14 charities
Brighton, East Sussex, UK

London 2 Brighton Ultra Challenge | 2nd Quarter

A great challenge through the Surrey & Sussex countryside – with a Sutton start and Turners Hill / Tulley’s Farm finish.

  • Enter online
  • Undulating
  • Hilly
  • Age 14 & over
  • 33 km trail running + 600 m ascent
A new 25 km 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 25 km 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

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