27

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.

Search by month

Search by place

Map

Events near me

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

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
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
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 2025
  • 13 charities
  • Sat 24 - Sun 25 May 2025
  • 13 charities
Crawley, West Sussex, UK

Sussex Marathon charity places

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 2025
  • 13 charities
  • Sat 24 - Sun 25 May 2025
  • 13 charities
Brighton, East Sussex, UK

London 2 Brighton Ultra Challenge | 2nd Quarter charity places

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 2025
  • 13 charities
  • Sun 25 May 2025
  • 13 charities
Brighton, East Sussex, UK

Brighton Challenge charity places

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
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
  • Sat 17 May 2025
Farnham, Surrey, UK

North Downs Way 50

  • 50 miles trail running
  • Sat 17 May 2025
Newbury, Berkshire, UK

Compton Challenge | 16 Mile

  • 16 miles trail running
  • Sat 17 May 2025
Newbury, Berkshire, UK

Compton Challenge | Marathon

  • 26.8 miles trail running
  • Sat 24 May 2025
Horndean, Hampshire, UK

UK Ultra South Downs 100 Miles

  • 100 miles trail running
  • Sun 25 May 2025
Arundel, West Sussex, UK

UK Ultra South Downs 100K

  • 100 km trail running
  • Sun 25 May 2025
Brighton, East Sussex, UK

UK Ultra South Downs 50K

  • 50 km trail running
  • Sun 25 May 2025
Buckingham, Buckinghamshire, UK

Trust 10K Run

  • 10 km trail running

Search options

Back to search options