Hilly Trail runs in South East in Winter
Find hilly 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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- Sat 10 Jan 2026
- £8-£28
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
- Sat 10 Jan 2026
- £27-£31
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
- Sat 10 Jan 2026
- £73-£115
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
- Sat 24 Jan 2026
- £26-£37.50
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
- Sat 31 Jan 2026
- £27-£31
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
- Sat 21 Feb 2026
- £26-£37.50
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
- Sat 28 Feb 2026
- £27-£31
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
- Sun 28 Dec
The Christmas Charity Run at Rathfinny
- 10 km trail running + 184 m ascent