Thirty Years of Contours - and the Dogs That Have Been Part of It!


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…

A doodled parade of all the Contours Holidays dogs: a mix of jack russells and Lancashire heelers, with a dachshund and cockerpoo for good measure.

Preamble: The Walking Habit That Built a Company

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.

Matt, a short-legged Jack Russell, poses with a stick while out on a walk.

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.

Contours Guided Walking Holidays

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.

Two New Four-Legged Friends

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, a long-legged Jack Russel, stands in a field while out guiding a long-distance walk.
Wooster, a Lancashire Heeler, sits in the grass while out on an early Contours Holiday.

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!

Taking a Different Path In 2001

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.

Contours Goes Self-Guided

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.

A handwritten sheet of directions lies on an Ordnance Survey map, depicting an early Contours self-guided walking holiday.

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.

The Arrival of Ralphee, Tia and the Internet

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.

A screenshot of the early Contours Holidays website, as seen through an old version of Internet Explorer. The webpage is virtually unstyled, with a white background, three columns and blue text.

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.

Ralphee, a Lancashire Heeler, trots through a field of bluebells.
Tia, an excessively long dachshund, makes her way along the beach.

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.

Expansion Runs Into Epidemic

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.

In their red Contours hoodies, staff head on a training walk into the countryside.

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.

Staff keep in touch via group Teams calls during the COVID lockdowns of 2020.
Office dog Maui the red lab mans a work-from-home station in 2020, situated in a farmhouse kitchen.

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.

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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.

Three New Cowalkers

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.

Mindy, an almost all-white Jack Russell, stands in a green field.
Fudge, a golden-brown cockerpoo, sits on the grass, a little wet from the rain.
Chip, a Lancashire heeler puppy, stands on green grass.

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.

And That Brings Us to Today

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.

Office dog Gino, a brown labrador, poses on a stone with the Lake District in the background as he helps research our Lake District Twin Centre tour.
A group of Contours staff, bundled up in our late autumn outdoor kit, stand on a bridge over a river in the Peak District.

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

Karen Simons, Managing Director of Contours Holidays, stands on a walking trail with her Jack Russell, Mindy, in the background.

Karen Simons

Managing Director

Walking is both mine and my dogs’ greatest pleasure.

Read more blogs by Karen Simons



Originally published 29/01/26


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