38 Trail runs in South East in May 2023

Find trail runs in and around South East in May 2023 - 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.

  • Mon 1 May 2023
  • £29.95
Gravesend, Kent, UK

The Funky Pants Challenge

Celebration of ever more colourful legwear!!

  • 6 hrs trail running
  • Mon 1 May 2023
  • £3
Tonbridge, Kent, UK

Hildenborough Road Races | ​Childrens Race - Preschool/Reception

The Hildenborough Road Races returns after three years on the first bank holiday Monday in May in this picturesque Kent village.

  • 400 m trail running
  • Mon 1 May 2023
  • £3
Tonbridge, Kent, UK

Hildenborough Road Races | ​Childrens Race - Years 1 & 2

The Hildenborough Road Races returns after three years on the first bank holiday Monday in May in this picturesque Kent village.

  • 600 m trail running
  • Mon 1 May 2023
  • £3
Tonbridge, Kent, UK

Hildenborough Road Races | ​Childrens Race - Years 3 & 4

The Hildenborough Road Races returns after three years on the first bank holiday Monday in May in this picturesque Kent village.

  • 800 m trail running
  • Mon 1 May 2023
  • £3
Tonbridge, Kent, UK

Hildenborough Road Races | ​Childrens Race - Years 5 & 6

The Hildenborough Road Races returns after three years on the first bank holiday Monday in May in this picturesque Kent village.

  • 1600 m trail running
  • Fri 5 May 2023
  • £24-£26
Egham, Surrey, UK

Chasing Numbers Time Turner Run

Join Saturn Running Events for a Chasing Number midweek run.

  • 7 hrs trail running
  • Fri 5 May 2023
  • £29.99-£31.99
Walton-on-Thames, Surrey, UK

PHOENIX Fridays - Wine Time Friday

Continuing the 'PHOENIX Fridays'; a series of Friday running events with flexible 'rock up and run' start times to suit you, here's our 'Wine Time Friday' - Thank Phoenix it's Friday!

  • 7 hrs trail running
  • Sun 7 May 2023
  • £39.95
Birchington, Kent, UK

VE Day 7 Hour Challenge

RunBelievable Challenges are delighted to bring you this special event to commemorate the 78th Anniversary of the end of World War 2 in Europe...!

  • 7 hrs trail running
  • Sun 7 May 2023
  • £37.95-£39.95
Dorking, Surrey, UK

The King's Coronation Run

Phoenix Running is absolutely delighted to be back at the wonderful Denbies Wines Estate for a very special run to commemorate the coronation of King Charles III (the day before our run).

  • 7 hrs trail running
  • Sun 7 May 2023
  • £15-£17
Midhurst, West Sussex, UK

Midhurst Milers Cocking Trail Race | 10K

Midhurst Milers warmly welcome you to the Cocking 10k Trail Race through the picturesque and challenging trails of the South Downs.

  • 10 km trail running
  • Sun 7 May 2023
  • £3
Midhurst, West Sussex, UK

Midhurst Milers Cocking Trail Race | 3K Junior

Midhurst Milers warmly welcome you to the Cocking 10k Trail Race through the picturesque and challenging trails of the South Downs.

  • 3 km trail running
  • Mon 8 May 2023
  • £33-£35
Egham, Surrey, UK

King Charles III Coronation Run

Saturn Running Events just had to hold a run to commemorate the coronation of King Charles III.

  • 7 hrs trail running
  • Sat 13 May 2023
  • £37.95-£39.95
Walton-on-Thames, Surrey, UK

Dinosaurs in Pyjamas Run

Phoenix Running is inviting you to a rather awesome Dinosaur's in Pyjamas Run. Will the fun just never end?

  • 6 hrs trail running
  • Sat 13 May 2023
  • £6
Arundel, West Sussex, UK

Arundel x Fauna | 2K Fun Run

Join Nice Work & Fauna in the beautiful surroundings of Arundel Castle.

  • 2 km trail running
  • Sat 13 May 2023
  • £16-£18
Arundel, West Sussex, UK

Arundel x Fauna | 5K

Join Nice Work & Fauna in the beautiful surroundings of Arundel Castle.

  • 5 km trail running
  • Sat 13 May 2023
  • £20-£22
Arundel, West Sussex, UK

Arundel x Fauna | 10K

Join Nice Work & Fauna in the beautiful surroundings of Arundel Castle.

  • 10 km trail running
  • Sun 14 May 2023
  • £37.95-£39.95
Walton-on-Thames, Surrey, UK

Panda Plod

Phoenix Running is inviting you to our brand new Panda Plod with an epic new medal.

  • 6 hrs trail running
  • Sun 14 May 2023
  • £12-£20
Lewes, East Sussex, UK

Focus 10K | Chailey Heritage Foundation | 10K

Join in and run a 10K, 5K or Kids Mini Mile on the stunning Vuggles Farm, Sutton Hall Estate.

  • 10 km trail running
  • Sun 14 May 2023
  • £6-£12.50
Lewes, East Sussex, UK

Focus 10K | Chailey Heritage Foundation | 5K

Join in and run a 10K, 5K or Kids Mini Mile on the stunning Vuggles Farm, Sutton Hall Estate.

  • 5 km trail running
  • Sun 14 May 2023
  • £33-£35
Staines, Surrey, UK

Rum not Run / Lucky dip medal

Join Saturn Running Events at Rum not Run / Lucky dip medal event to earn an amazing piece of bling bling you absolute gorgeous bunch of drinkers

  • 7 hrs trail running
  • Sun 14 May 2023
  • £10-£20
Reading, Berkshire, UK

First Days Colour Run

A unique event where you finish a different colour or two to the one you started.

  • 2.5 km trail running
  • Fri 19 May 2023
  • £24-£26
Egham, Surrey, UK

Chasing Numbers Run - Chamber of Runs Harry Potter

Join Saturn Running Events for Chasing Numbers - Harry Potter Chamber of Secrets Run down at our Runnymede course.

  • 7 hrs trail running
  • Sat 20 May 2023
  • £80
Herne Bay, Kent, UK

Saxon 100 - Saxon Challenges | 24 Hour Challenge

A one off 100 Mile Run around Saxon Country!

  • 24 hrs trail running
  • Sat 20 May 2023
  • £175
Herne Bay, Kent, UK

Saxon 100 - Saxon Challenges | 100 Mile

A one off 100 Mile Run around Saxon Country!

  • 100 miles trail running
  • Sun 21 May 2023
  • £13.50
Woodstock, Oxfordshire, UK

Blenheim 7K | 1 Mile

4 Races, 1 Magical Day

  • 1 mile trail running
  • Sun 21 May 2023
  • £28
Woodstock, Oxfordshire, UK

Blenheim 7K | 4 Mile

4 Races, 1 Magical Day

  • 4 miles trail running
  • Sun 21 May 2023
  • £28
Woodstock, Oxfordshire, UK

Blenheim 7K | 7K

4 Races, 1 Magical Day

  • 7.4 km trail running
  • Sun 21 May 2023
  • £28
Woodstock, Oxfordshire, UK

Blenheim 7K | 7K+dog

4 Races, 1 Magical Day

  • 7 km trail running
  • Sun 21 May 2023
  • £5
Henley-on-Thames, Oxfordshire, UK

Nettlebed Stinger | The Little Stinger

A challenging 10km trail run set in the beautiful Chiltern Hills surrounding the village of Nettlebed.

  • 200 m multi terrain running
  • Sun 21 May 2023
  • £5
Henley-on-Thames, Oxfordshire, UK

Nettlebed Stinger | Stinger Cubs Run

A challenging 10km trail run set in the beautiful Chiltern Hills surrounding the village of Nettlebed.

  • 2 km multi terrain running
  • Sun 21 May 2023
  • £20-£22
Henley-on-Thames, Oxfordshire, UK

Nettlebed Stinger | 10K

A challenging 10km trail run set in the beautiful Chiltern Hills surrounding the village of Nettlebed.

  • 10 km multi terrain running
  • Sun 21 May 2023
  • £15
Tring, Buckinghamshire, UK

Marsworth 10K Fun Run

The Marsworth 10K returns in 2023.

  • 10 km trail running
  • Sun 21 May 2023
  • £5
  • Entries closed
Lewes, East Sussex, UK

East Hoathly 10K, 5K and Family Fun Run | 1K

Family-friendly fun runs in a beautiful rural village. Fancy dress optional!

  • Entries closed
  • 1 km multi terrain running
  • Fri 26 May 2023
  • £29.99-£31.99
Walton-on-Thames, Surrey, UK

PHOENIX Fridays - Retro Fridays

Continuing the 'PHOENIX Fridays'; a series of Friday running events with flexible 'rock up and run' start times to suit you, here's our 'Retro Friday' - Thank Phoenix it's Friday!

  • 7 hrs trail running
  • Sat 27 May 2023
  • £29.95
Gravesend, Kent, UK

The Centenary Series Challenge - Le Mans

1923 was quite a famous year for things that are still going strong a century later!

  • 6 hrs trail running
  • Sun 28 May 2023
  • £29.95
Gravesend, Kent, UK

The Centenary Series Challenge - Hollywood

1923 was quite a famous year for things that are still going strong a century later!

  • 6 hrs trail running
  • Sun 28 May 2023
  • £33-£35
Reading, Berkshire, UK

Teenage Mutant Ninja Runners - Part 2

Come and earn the second part of a set of Teenage Mutant Ninja Runners medal which create one large pizza medal!

  • 7 hrs trail running
  • Mon 29 May 2023
  • £29.95
Gravesend, Kent, UK

The Centenary Series Challenge - Tutankhamun

1923 was quite a famous year for things that are still going strong a century later!

  • 6 hrs trail running

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