Challenge Events

Take on an epic challenge event and...

  • Provide a fresh Start for someone who is street homeless.
  • Move someone out of unsafe or unsuitable accommodation.
  • Stop an illegal or unfair eviction and keep a household in their home.
  • Run our homeless helpline and more!

Sign up to do a bungee jump, take on an ultra walk, an inflatable obstacle course, a Tough Mudder, do a distance run or more! You’ll get:

  • A FREE or discounted place.
  • A FREE branded WHC sports T-shirt with our logo and your name.
  • A fantastic feeling of having helped tackle homelessness.
  • A dedicated point of contact in our Fundraising team to give you lots of support, encouragement and help with fundraising!

We have lots of exciting ways that you can support our life saving work this year. Click on the links below to check them out.

Got your own place but want to fundraise for us? Brilliant! We can support you - get in touch via 01494 449699 or communications@wyhoc.org.uk

Meet our Challenge Eventers

Caroline from Willow and White Interiors ran the Chiltern Ridge Half Marathon in July

Check out her challenge

Dane our Volunteering Coordinator conquered 100k in July!

Check out his challenge

Nik and Victoria took on Ben Nevis!

Check out their challenge

Rev Jonny ran the Milton Keynes Marathon on 4 May 2026!

Check out his challenge

Check out our exciting range of challenge events below

Featured Challenge Events

Wendover Woods Running Festival

22 August 2026

Wendover Woods Running Festival

Take on a rewarding trail run through Wendover Woods with spectacular scenery from start to finish. The routes wind through woodland paths with open viewpoints over the Chilterns. Choose your distance from 5k,10k, Half Marathon or Junior Race and enjoy clear waymarking, friendly marshals, and a celebratory finish the whole family can enjoy. The Junior Race brings extra energy to the day.

Ground conditions are on gravel and trail paths throughout, creating a natural, scenic challenge that rewards steady pacing and confident footing.

Learn more  
Windsor Trail Run

30 August 2026

Windsor Trail Run

Wrap up the summer with the Windsor Trail Run on Sunday 30th August 2026. This event takes you through the beautifully kept paths of Alexandra Gardens and with Windsor Castle towering in the distance.

Offering 10K and Half Marathon distances, the flat trail course is ideal for runners of all abilities. Take in the sights, enjoy the supportive atmosphere, and cross the finish line in one of the most historic and scenic running locations in the UK.

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Henley River Half Marathon

5 September 2026

Henley River Half Marathon

The Henley River Half Marathon, 10K & Juniors offers another chance to enjoy this stunning route before the season ends. With fast, undulating trails and plenty of atmosphere, it’s the perfect late-summer race.

Race alongside the Thames with support from fantastic marshals and enjoy a route designed to inspire PBs and personal achievements. As always, the course begins and ends at the iconic Temple Island Meadows.

Learn more  
Tough Mudder - London South

19 September 2026

Tough Mudder - London South

The ultimate obstacle course challenge now has 20+ obstacles over a 15 Kilometre run. With no competition and no timing, it’s just you, your teammates and muddy strangers working together to conquer the course and earn the world-famous orange headband.

Included in ticket: • Finishers Medal • Finisher Shirt • Finishers Headband • Free Parking

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Queen Elizabeth Olympic Park 5k & 10k

19 September 2026

Queen Elizabeth Olympic Park 5k & 10k

Come and run a chip timed 5k or 10k through the incredible grounds of London’s Queen Elizabeth Olympic Park. The RunThrough Queen Elizabeth Olympic Park 5k & 10k event is a great opportunity for a fun morning out with a unique themed medal waiting for you at the finish!

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160ft Bungee - Birmingham

26 September 2026

160ft Bungee - Birmingham

The Birmingham bungee jump location takes in the breathtaking views at Cliff Lakes Watersports Park, it is the only regular bungee jump location in the Midlands with the bungee jumping experience taking place over the watersports lake. The site is situated just outside Tamworth and within 30mins of Birmingham centre close to the M42 and M6 motorway junctions.

The location also offers more activities should you wish, the Aqua Park is perfect for a family day out and will create unforgettable memories. They have a team of expert coaches who can teach you how to wakeboard and water-ski on the purposely sculpted lakes. Finally, finish your day off with a drink and a snack overlooking our stunning lake!

Learn more  

Other Upcoming Challenge Events

5k Inflatable races

Various times

5k Inflatable races

Bounce your way through The World’s BIGGEST and most EPIC Inflatable 5K obstacle course! The excitement has been pumped up to the MAX, you’ll be jumping, sliding, and bouncing your way to the finish line like never before.

So grab your friends, lace up your trainers, and get ready for the ultimate inflatable adventure!

Learn more  
Tough Mudders

Various dates

Tough Mudders

The ultimate obstacle course challenge now more obstacles than ever before! With no competition and no timing, it’s just you, your teammates and muddy strangers working together to conquer the course and earn the world-famous orange headband.

Learn more  
Full range of events at Run for Charity

All year round

Full range of events at Run for Charity

Find hundreds more events at our partner site, Run for Charity. Whether it be running, pushing, jogging, jumping, walking - there is something on almost every weekend of the year locally and across the UK. Accessible events for all ages and abilities.

Learn more  
Ultra Challenges

Ultra Challenges

Explore unique events available on the Ultra Challenge website, and sign up for one of the UK’s #1 endurance events.

As a team or individual you can walk, jog or run 25k, 50k, 75k or 100k challenges across the UK.

Learn more