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Challenge walks in Maidstone

Find challenge walks near me in Maidstone for 2025/2026 - search by date or place, display on a map or use the advanced search to find your perfect race.

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Set in an Area of Outstanding Natural Beauty offering dramatic views, vibrant communities, a rich historic heritage, and diverse wildlife and habitats – featuring the North Downs Way National Trail.
  • Sat 11 Oct
  • £139
  • 6 charities
  • Sat 11 Oct
  • £139
  • 6 charities
Maidstone, Kent, UK

Kent Downs 50 Ultra Challenge | 50km

Set in an Area of Outstanding Natural Beauty offering dramatic views, vibrant communities, a rich historic heritage, and diverse wildlife and habitats – featuring the North Downs Way National Trail.

  • Chip timing
  • Enter online
  • GPS tracking
  • Undulating
  • Age 16 & over
  • 50 km trail running + 1000 m ascent
The 25km loop sits within the 50km loop and splits off at the picturesque village of Aylesford - one of the River Medway’s hidden jewels heading east on Augustine Camino to Detling via Boxley.
  • Sat 11 Oct
  • £89
  • 6 charities
  • Sat 11 Oct
  • £89
  • 6 charities
Maidstone, Kent, UK

Kent Downs 50 Ultra Challenge | 25km

The 25km loop sits within the 50km loop and splits off at the picturesque village of Aylesford - one of the River Medway’s hidden jewels heading east on Augustine Camino to Detling via Boxley.

  • Enter online
  • GPS tracking
  • Undulating
  • Age 14 & over
  • 25 km trail running + 450 m ascent

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