Thirty Years of Contours - and the Dogs That Have Been Part of It!
We celebrate Contours' thirty year anniversary with a little look back at how the business took shape.
Thirty Years of Contours - and the Dogs That Have Been Part of It!
https://www.contours.co.uk/thirty-years-of-contours-holidays
Contours Holidays are excited to celebrate our thirty-year anniversary — making us one of the oldest and most established walking holiday companies in the country!
Today, we delight thousands of walkers and runners a year with brilliant self-guided adventures. Thirty years ago, we were driven by that same love of the outdoors, though our offerings were a little different. Our founder and managing director, Karen Simons, reflects on how the modern-day Contours Family came to be…
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Walking is a passion, and it is in your blood, especially if you are born into a family who walk everywhere for pleasure as well as exercise.
In my family, any spare time was spent exploring new parts of the country on foot, and this led to trying multiday walks along long-distance trails. The first trail completed was the Cleveland Way, still my favourite, but with bad memories of trying to backpack along the extremely overgrown ‘Missing Link’ to complete the circle.

Many more adventures followed, all joined by Matt, a plucky little Jack Russell who would walk all day and crawl into a sleeping bag with you at night.
We ticked off more trails, such as the Coast to Coast, Peak District challenges and sections of the South West Coast Path, before Matt hung up his little boots.
Matt’s departure marked a change of career and the first tentative steps towards making a living from a hobby: Contours Guided Walking Holidays began to form.
It took a lot of false starts and hard work. Firstly, we had to decide which Long Distance Trails we could offer and start planning out our routes from single centres across the country. These were graded easy, moderate and challenging, and often involved us being in Scotland one week and then the Welsh coast or Isle of Wight the next.
It was in the days before the internet, so adverts were placed in walking magazines, tourist boards and friendly accommodations — a brochure produced, leaflets distributed — and then we sat back and waited for a telephone call or letter to arrive.
As bookings came in, we slowly built a customer base, becoming more confident that Contours might work. Family and friends helped with guiding, transport and admin from our home office in the Lake District, ably supported by Pip, our new Jack Russell.
Pip was extremely fit and came on all the walks. A great hit with everyone, she was wonderful company helping to motivate and keep folk entertained. She loved water, and if we were ever able to stop and let her swim, she would go to bed happy that night.


Pip was then joined by Wooster, our first Lancashire Heeler. He came at eight weeks old whilst a guided Hadrian’s Wall Walk was taking place, so I carried him in my ‘bum bag’ each day, and that was it: he never missed another walk. Although not as quick as Pip, he was steady, never tiring. In fact, if any of the group stopped for too long, he would start to moan!
Having ploughed all we had into running Contours, it was a huge shock to have it come to an immediate halt some five years later with the foot-and-mouth crisis in 2001.
We were at the epicentre in Cumbria, but across the country, all footpaths were closed, meaning that we could not trade. Pip did a lot of swimming that summer.
Unlike farmers, the tourist trade did not get any compensation. By the time the country slowly emerged from the restrictions, we had decided to introduce self-guided holidays in addition to the guided tours to help us diversify.
For our new self-guided holidays, we chose trails spread out across the country, offering as big a selection as possible. We selected popular National Trails, little-known trails and our own bespoke routes. These we split as best we could into varying daily mileages, depending on where we could get rooms.

The other important consideration right from the start was to be able to cater for solo walkers, groups and (of course) our four-legged friends.
As we built up a portfolio of self-guided holidays, they became ever more popular. Our office in Cumbria expanded and then moved first to the Peak District and eventually our offices near Matlock.
As Wooster went into retirement, along came a bundle of joy called Ralphee. Ralph was a Lancashire Heeler who exploded into our lives and the growing Contours Family. He had been kept in a kennel, so for the rest of his life, there was nothing more important than being free and enjoying himself.
By then, the internet having arrived with a bang, Contours was changing. Gone were the index cards and leaflet drops as we launched a website. A good friend built us the database that we still use today.

Pip, who really had been a founding member of the first Contours Holidays, saw all the changes and embraced her standing as the matriarch of the family. She walked to the end, showing Ralphee how it was done and then handing over to Tia, a standard dachshund.


Tia captured everyone’s hearts. As the company grew, so did she, to become a rather long, beautiful girl whose short legs took her on so many adventures as we went on research trips for our new offerings.
We introduced trail running holidays and expanded our walking options with more challenging mountainous routes, stile-free and short mileage trails, and single- and twin-centre holidays, all supported by our faithful staff and growing numbers of dog companions.

However, another blow hit us when the pandemic struck in 2020 and all trading stopped. Overnight, we became home workers, where our loyal staff handled the difficult job of cancelling that year’s holidays whilst keeping the core business alive.
I am proud to say that Contours initiated and led a group of interested partners to bring the tourism plight in front of the government.


Coming out of the pandemic was not straightforward. We experienced a few false starts, and accommodations across the country had suffered, many closing or becoming holiday lets.
Fortunately, not only did all the staff remain committed to getting us back on track, but so many of our wonderful clients patiently supported our return.

We never take our clients for granted. Each booking is as important as the last: be it from a regular loyal customer, a first-time walker or a party from abroad, each will be given the personal service of our family-run business.
During this time, we lost Tia the unfeasibly long sausage dog, and another Jack Russell, Mindy, joined the team. Mindy followed Ralphee, who by now was an old hand, and learnt all his tricks.
But too soon we knew that our beloved Ralph would leave, and before we could search out another Heeler, our Cockerpoo, Fudge, found his way into our hearts. Fudge, who is completely Cocker and no Poo, is by far the most active dog that has ever been. Mileage means nothing to him so long as he can run — mainly in circles it seems.



Fate then intervened when a feisty little Lancashire Heeler who we called Chip was found and our lives were turned upside-down. Chip was very poorly but survived beyond all the odds. He would be carried up to the office at the top of the mill building where work would stop whilst he was entertained.
After thirty years, we have a team that really are ‘The Contours Family’. We have a hybrid way of working that gives us the flexibility of being in the office, out in the field and at home. Our vision remains the same:
To be the most trusted brand in the outdoor self-guided holiday market, offering an unrivalled selection of trails across the UK. To grow the brand through constant innovation, with new trails, alternative options, and trialling and testing new concepts and ideas.


One last word from Chip — he has gone for long term healthcare in Lyme Regis, soaking up the sun on the south coast!

Managing Director
Walking is both mine and my dogs’ greatest pleasure.
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