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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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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 20 Dec
  • £19
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.

  • Beginner-friendly
  • Dogs allowed at venue
  • Event village
  • Age 18 & over
  • Trail run
  • CaniCross
It's December, so what better way to finish the year than with a Christmas event? Follow the Windmill Way route over half marathon distance.
  • Sat 20 Dec
  • £27-£32
Bury Saint Edmunds, Suffolk, UK

Christmas Canter | Half Marathon

It's December, so what better way to finish the year than with a Christmas event? Follow the Windmill Way route over half marathon distance.

  • Chip timing
  • Enter online
  • Hilly
  • Age 18 & over
  • 13.1 miles road running + 764 ft ascent
The Dark Skies returns for an undulating yomp through Surrey’s muddy, rolling hills and feature a thrilling 5K, 10K, 10 Mile, kids races and canicross with hot food and drinks, medals, kit and prizes.
  • Sat 10 Jan 2026
  • £8-£28
Dorking, Surrey, UK

Dark Skies Surrey Hills

The Dark Skies returns for an undulating yomp through Surrey’s muddy, rolling hills and feature a thrilling 5K, 10K, 10 Mile, kids races and canicross with hot food and drinks, medals, kit and prizes.

  • Families
  • Beginner-friendly
  • Plastic bottle free
  • Dogs allowed at venue
  • Event village
  • Rural
  • Sustainability policy
  • Plastic-free event
  • Age 3 & over
  • Fun run 2
  • 5K run
  • 10K run
  • 10 miler
  • CaniCross 2
Take on a tough, award-winning trail run in the Surrey Hills and North Downs with a cracking sunrise, stop-in-your-tracks views and five-star reviews! No nonsense trail running.
  • Sat 10 Jan 2026
  • £27-£31
Guildford, Surrey, UK

Fitstuff G3 Run Series | Race 1

Take on a tough, award-winning trail run in the Surrey Hills and North Downs with a cracking sunrise, stop-in-your-tracks views and five-star reviews! No nonsense trail running.

  • Trees not tees
  • Beginner-friendly
  • Event village
  • Rural
  • Sustainability policy
  • Plastic-free event
  • Age 15 & over
  • 10K run
  • Trail run
A crisp morning start from the farm on a 50/50 road-trail mix with coastal views. Run a loop (a 'yard') every hour, on the hour, until only one runner remains. Miss the bell, and you're out.
  • Sat 10 Jan 2026
  • £73-£115
Dover, Kent, UK

Kent Backyard Ultra | Round Two: Dover

A crisp morning start from the farm on a 50/50 road-trail mix with coastal views. Run a loop (a 'yard') every hour, on the hour, until only one runner remains. Miss the bell, and you're out.

  • Beginner-friendly
  • Event village
  • Rural
  • Age 16 & over
  • Fixed time runs
  • Ultra 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.
  • Sat 17 Jan 2026
  • £20
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.

  • Enter online
  • Hilly
  • Traffic free
  • Age 8 & over
  • 5 km trail running + 528 ft 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 24 Jan 2026
  • £26-£37.50
Gerrards Cross, Buckinghamshire, UK

Running Tribe Races | Jan | 14K

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
  • Hilly
  • Age 16 & over
  • 14 km multi terrain running + 1754 ft ascent
Take on a tough, award-winning trail run in the Surrey Hills and North Downs with a cracking sunrise, stop-in-your-tracks views and five-star reviews! No nonsense trail running.
  • Sat 31 Jan 2026
  • £27-£31
Guildford, Surrey, UK

Fitstuff G3 Run Series | Race 2

Take on a tough, award-winning trail run in the Surrey Hills and North Downs with a cracking sunrise, stop-in-your-tracks views and five-star reviews! No nonsense trail running.

  • Trees not tees
  • Beginner-friendly
  • Event village
  • Rural
  • Sustainability policy
  • Plastic-free event
  • Age 15 & over
  • 10K run
  • Trail run
Join this spellbinding trail race through dappled sunlight at Cannock Chase Forest. And, with two additional distances to choose from... It's going to be a corker!
  • Sun 8 Feb 2026
  • £23-£33
Rugeley, Staffordshire, UK

Cannock Chase Forest 20, 15, 10 & 5 Mile

Join this spellbinding trail race through dappled sunlight at Cannock Chase Forest. And, with two additional distances to choose from... It's going to be a corker!

  • Families
  • Recycling
  • Beginner-friendly
  • Plastic bottle free
  • Event village
  • Rural
  • Sustainability policy
  • Public transport links
  • Age 15 & over
  • Trail run 3
  • 10 miler
An undulating 6.5 mile loop with a mixture of canal tow path, river bank, trail and a road – a little bit of everything with beautiful sections of the Leeds Liverpool canal and River Aire.
  • Sun 8 Feb 2026
  • £24-£42
Leeds, West Yorkshire, UK

Grim Leodis

An undulating 6.5 mile loop with a mixture of canal tow path, river bank, trail and a road – a little bit of everything with beautiful sections of the Leeds Liverpool canal and River Aire.

  • Beginner-friendly
  • Plastic bottle free
  • Event village
  • Sustainability policy
  • Age 16 & over
  • Trail run 2
  • Half marathon
  • Marathon
This is a toughish race on Dartmoor but it's a big old moon so visibility will be good and the weather looks mild. Grab your head torch and let's get wild.
  • Sat 14 Feb 2026
  • £23-£28
South Brent, Devon, UK

Wild & Mild Night Run

This is a toughish race on Dartmoor but it's a big old moon so visibility will be good and the weather looks mild. Grab your head torch and let's get wild.

  • Beginner-friendly
  • Music
  • Event village
  • Rural
  • Age 18 & over
  • Trail run 2
A new and unique concept where you decide how many loops you feel capable of on the day - whether it's 7km, 14km, Half Marathon, Full Marathon or an Ultra Marathon! Push yourself further or go easy.
  • Sat 21 Feb 2026
  • £26-£37.50
Gerrards Cross, Buckinghamshire, UK

Running Tribe Races | Feb

A new and unique concept where you decide how many loops you feel capable of on the day - whether it's 7km, 14km, Half Marathon, Full Marathon or an Ultra Marathon! Push yourself further or go easy.

  • Beginner-friendly
  • Dogs allowed at venue
  • Event village
  • Park
  • Rural
  • Public transport links
  • Age 16 & over
  • Multi-terrain run 2
  • Half marathon
  • Marathon
  • Ultra run
A tough but rewarding day out with great views! Run as many 3.3-mile laps as you wish. If you like uphills, you’ll love the first half of the lap. If you love downhills, you’ll love the second half!
  • Fri 27 Feb 2026
  • £33.30-£39
Woodhouse Eaves, Leicestershire, UK

Badger Challenge & Canicross

A tough but rewarding day out with great views! Run as many 3.3-mile laps as you wish. If you like uphills, you’ll love the first half of the lap. If you love downhills, you’ll love the second half!

  • Trees not tees
  • Beginner-friendly
  • Dogs allowed at venue
  • Event village
  • Park
  • Sustainability policy
  • Age 18 & over
  • Trail run
  • CaniCross
Take on a tough, award-winning trail run in the Surrey Hills and North Downs with a cracking sunrise, stop-in-your-tracks views and five-star reviews! No nonsense trail running.
  • Sat 28 Feb 2026
  • £27-£31
Guildford, Surrey, UK

Fitstuff G3 Run Series | Race 3

Take on a tough, award-winning trail run in the Surrey Hills and North Downs with a cracking sunrise, stop-in-your-tracks views and five-star reviews! No nonsense trail running.

  • Trees not tees
  • Beginner-friendly
  • Event village
  • Rural
  • Sustainability policy
  • Plastic-free event
  • Age 15 & over
  • 10K run
  • Trail run
Take on lapped course through the stunning South Yorkshire Park country park of Rabbit Ings and reach the finish to hang your finisher's medal around your neck with pride.
  • Sat 28 Feb 2026
  • £24-£56
Barnsley, South Yorkshire, UK

Carry on in the Colliery

Take on lapped course through the stunning South Yorkshire Park country park of Rabbit Ings and reach the finish to hang your finisher's medal around your neck with pride.

  • Beginner-friendly
  • Dogs allowed at venue
  • Event village
  • Park
  • Age 16 & over
  • Trail run 3
  • 10 miler
  • Marathon
  • Ultra run
  • CaniCross
  • Wed 24 Dec
Thatcham, Berkshire, UK

Santa Claws 10K

  • 10K run
  • CaniCross
  • Sun 28 Dec
Polegate, East Sussex, UK

The Christmas Charity Run at Rathfinny

  • 10 km trail running + 184 m ascent
  • Sun 11 Jan 2026
Fife, UK

The Full MacTuff New Year

  • Obstacle race 3
  • Sat 14 Feb 2026
Keswick, Cumbria, UK

Whinlatter Moon Runner 10K Head Torch Trail Race

  • 10 km trail running
  • Sat 21 Feb 2026
Leeds, West Yorkshire, UK

The Leeds 5K, 10K and Half Marathon Winter Warmer Run

  • 5K run
  • 10K run
  • Half marathon

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