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Beginner-friendly Trail runs in South East in Winter

Find beginner-friendly trail runs in South East in Winter - filter by date, location or category, display on a map or use the advanced search to find your perfect race.

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Climb from valley to summit on a guided hill-challenge up Box Hill and surrounding area, tackling steep woodland trails and gritty elevation in one of southern England’s toughest guided trail runs.
  • Sat 5 Dec
  • £19
Dorking, Surrey, UK

Box Hill Vertical KM

Climb from valley to summit on a guided hill-challenge up Box Hill and surrounding area, tackling steep woodland trails and gritty elevation in one of southern England’s toughest guided trail runs.

  • 12.5 miles trail running + 1000 m ascent
  • Beginner-friendly
  • Enter online
  • Hilly
  • Event village
  • Mountains
  • Age 18 & over
A new and unique concept where you decide how many loops you feel capable of on the day from 7km up to an ultra marathon! Push yourself further or go easy.
  • Sat 12 Dec
  • £26-£37
Gerrards Cross, Buckinghamshire, UK

Running Tribe Races | Dec

A new and unique concept where you decide how many loops you feel capable of on the day from 7km up to an ultra marathon! Push yourself further or go easy.

  • 1 day multi terrain running
  • Beginner-friendly
  • Dogs allowed at venue
  • Enter online
  • Undulating
  • Hilly
  • Traffic free
  • Park
  • Rural
  • Public transport links
  • Age 16 & over
A fabulous 43-mile point-to-point race, well established as the season opener to the Ultra race calendar and always sells out. From the countryside along the Grand Union Canal into London.
  • Sat 9 Jan 2027
  • £85
Aylesbury, Buckinghamshire, UK

Country to Capital Ultra

A fabulous 43-mile point-to-point race, well established as the season opener to the Ultra race calendar and always sells out. From the countryside along the Grand Union Canal into London.

  • 43 miles trail running + 1404 ft ascent
  • Recycling
  • Beginner-friendly
  • Chip timing
  • Enter online
  • GPS tracking
  • Undulating
  • Event village
  • Age 18 & over
  • Sat 5 - Sun 6 Dec
  • £183-£185
Lewes, East Sussex, UK

Winter On The Downs 100 Miles

  • 100 miles trail running
  • Sat 5 - Sun 6 Dec
  • £110-£112
Lewes, East Sussex, UK

Winter On The Downs 55 Miles

  • 55 miles trail running

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