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What to expect on our challenge holidays

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January is often a time for reflecting on our successes and achievements and how we can better them in the year to come. Make 2024 the year you do something you never thought possible with a walking holiday that requires more stamina but assures a huge sense of achievement. 

Take on an exhilarating challenge walk with the help of our experienced HF Holidays Leaders and tick-off some of the UK’s highest mountains and wildest landscapes. We take care of everything; from planning to navigation. You just need to focus on the joy of the journey.

What is a challenge holiday?

Challenges are an excellent opportunity for growth. Not only do they test your commitment, but they reward with a win. They teach you to be more resilient, braver, and far more capable than you ever imagined you could be. Your challenge, should you choose to accept it, will push you out of your comfort zone and into trying something new.

Can anyone join a challenge holiday?

The majority of our challenge holidays are suitable for anyone with a reasonable level of fitness and a few miles under their belt. However, trips such as our Wainright bagging breaks in the Lake District require more stamina and experience of prolonged mountain walking.  

You can expect 6-8 hours of hill walking a day over some of England’s most challenging terrain, so it’s a good idea to practise on similar routes prior to your trip. Each of our walking holidays is graded on a scale of 1 to 6, with 1 being the gentlest and 6 the most challenging.  

For more information, read our Walking Grades Explained blog, here. 

How long are challenge holidays?

They range from three nights (a long weekend) to seven nights.

Where do I stay?

You’ll be staying at one of our characterful country houses, all of which are located in some of the UK’s best-loved national parks and National Landscapes. Enjoy a full-board break that includes cooked or continental breakfasts to set you up for the challenges ahead, daily packed lunches, plus delicious three-course evening meals ideal for refuelling after a long day of walking. Best of all, you’ll be part of a group of like-minded challenge-seekers and have plenty of opportunity for swapping stories over dinner or simply relaxing at the bar.

Five of our favourite challenge holidays

Scafell Pike Challenge

Scafell Pike

As England’s highest mountain, Scafell Pike looms large over the Lake District. And if you’re keeping tabs of the Wainwrights you’re bagging, this one is as dramatic as they come. Guided by an experienced HF Holidays Leader, you and your group will take the tough-but-rewarding trek to the summit. At the top, you’ll have outstanding views and be higher than anyone else for miles around. The best part is that it’s a challenge many can achieve.

Helvellyn via the Edges Challenge


While there are many ways to climb Helvellyn - the third-highest peak of both the Lake District and England - reaching the summit via Striding Edge and descending along Swirral Edge must be one of the most spectacular. Under the guidance of an experienced HF Holidays Leader, you can expect amazingly beautiful views, not to mention a real feeling of accomplishment.

Wainwright Bagging Northern Fells Challenge

Wainwright’s Northern and Eastern Fells of the Lake District

Follow in the footsteps of Alfred Wainwright as you embark on this week-long exploration of the Lake District together with a group of like-minded walkers and an experienced HF Holidays Leader. You can choose to tackle Wainwright’s Northern Fells, bagging four to six in a day, or Wainwright’s Eastern Fells, which sees you bagging no less than 35 over the course of the week.

Ben Nevis Challenge

Ben Nevis

Located in the Western Highlands, near the town of Fort William and part of the Grampian Mountain range, Ben Nevis attracts 125,000 walkers every year. Accompanied by an experienced HF Holidays Leader, you’ll get to conquer Britain’s highest peak and enjoy serious bragging rights. There’s also gorgeous views over Glen Nevis and beyond on a clear day.

Yorkshire Three Peaks Challenge

Yorkshire Dales

Take on the famous Yorkshire Three Peaks challenge by conquering the summits of Pen-y-ghent, Whernside, and Ingleborough over a weekend. Not only will you get to complete the trio of the county’s highest mountains, but you’ll enjoy fabulous views of Ingleborough from the summit of Whernside, marvel at the Ribblehead Viaduct and railway, and walk sections of the Pennine Way – the cherished National Trail offering 268 miles of upland walking.

Looking for a gentler option to start the new year? Book a self-guided holiday at one of our country houses and discover the best the UK countryside has to offer at your own pace.

3 Night Shropshire Hills Self-Guided Walking

Book now or call 020 3974 8865

7 Night Southern Yorkshire Dales Self-Guided Walking

Book now or call 020 3974 8865

7 Night Isle of Wight Self-Guided Walking

Book now or call 020 3974 8865

3 Night Peak District Self-Guided Walking

Book now or call 020 3974 8865

Published 16th January 2024