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Hilly Trail runs in Winter

Find hilly trail runs near me 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
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
A great chance to stretch your legs with this event on the last Saturday before Christmas, with a Canicross race going off before the main pack.
  • Sat 19 Dec
  • £19.50
Mold, Clwyd, UK

Moel Famau Festive 'Piece of String' Race

A great chance to stretch your legs with this event on the last Saturday before Christmas, with a Canicross race going off before the main pack.

  • Trail run
  • CaniCross
Storm the Fort 5K is the Gold award-winning event in the ‘Dark Skies Series’ of night trail running events, a three-event series taking part across Somerset.
  • Sat 16 Jan 2027
  • £21
Burnham-on-Sea, Somerset, UK

Dark Skies Series | Storm the Fort | 5K Night Run

Storm the Fort 5K is the Gold award-winning event in the ‘Dark Skies Series’ of night trail running events, a three-event series taking part across Somerset.

  • 5 km trail running + 528 ft ascent

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