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n/a days
Grade 1

About the challenge

Our challenge is to cycle the breadth of the UK across some of the most spectacular and wild countryside that England has to offer.  Leaving the West Coast we head inland, carving our way over the Cumbrian Mountains and southwards through the Lake District National Park. From Kendal we head east, crossing into Yorkshire, through the heart of the famous Dales and onto our destination: the East Coast and the historic town of Whitby. Our route takes us ‘up pass and down dale’ as we traverse the country: gruelling climbs, magnificent descents and stunning scenery await us! This is a challenge for the hardy, taking whatever the Lakes and the Dales might throw at us. We will feel a wonderful sense of achievement when we reach the fabulous town of Whitby!

********* LATE AVAILABILITY ***********
Book a place on this ride before 31 July and we will deduct £50 off the trip cost.


The itinerary

Day 1: Workington – Kendal
Cycle approx. 54 miles

Leaving the rugged coastline of the West Coast, we head into the winding lanes that lead us to the foothills of the Cumbrian Mountains. We encounter the challenging Whinlatter Pass standing over 350m above sea level; our first challenge before dropping down into the picturesque town of Keswick. Passing many of the lakes that make this area famous we cycle past Derwent Water, Thirlmere and Windermere as well passing beneath the slopes of one of England’s highest mountains, Hellvelyn. We plough on to our evening’s destination in Kendal. Here we are rewarded by a hot shower and some wholesome food to replenish our energies ready for our next day in the saddle.

Day 2: Kendal – Richmond
Cycle approx. 53 miles

After a hearty breakfast we head east, leaving behind the beautiful Lake District and crossing the county boundary into Yorkshire and its stunning Dales. Our route today sees some steep climbs rising to over 300m at the highest point. We pass thorough Sedbergh, Hawes and Leyburn as we snake our way across the beautiful Yorkshire Dales National Park towards Richmond. Night in Hotel

Day 3: Richmond - Whitby
Cycle approx. 57 miles

Our final day’s ride has a more gentle start before we tackle the Cleveland Hills and North York Moors with 1:3 gradients! We are of course rewarded by fabulous views (on a clear day) across the Moors and down to the coast, which makes it all worthwhile after all that effort! What better way to end than cycling the last section south along the spectacular coastal road, with some great freewheeling descents into the historic town of Whitby. Home to the infamous Captain Cook and HMS Endeavour, the town makes a fitting finish to a tough but awesome ride. After finishing at the seafront we make our way to the hotel for a well-earned celebration.

Day 4: Depart Whitby

After breakfast we say our good-byes and head for home.

Discover Adventure reserves the right to change the route or itinerary for safety reasons should local conditions dictate.

Detailed information

What's Included?

All accommodation is included, as well as all meals (other than breakfast on Day 1). It also includes full trip support of experienced Discover Adventure leaders, drivers and mechanics.

What's Excluded?

It does not include personal travel insurance, one meal as specified, personal items and entry to any optional tourist sites you may wish to visit or a bike! Remember to allow extra for drinks, souvenirs and other personal expenses. We strongly recommend you carry a credit card in case of personal emergency.


Our accommodation is generally in larger hotels, though there may be some B&Bs. Be prepared for variety! Accommodation is comfortable and well situated but not luxurious. Rooms are usually twin-share and have en-suite facilities. Due to accommodation restrictions in certain areas, the night-stops as shown in the itinerary may change in order to accommodate different-sized groups.


All food is included during the cycle other than 1 meal as specified in the itinerary. Lunches are generous buffet-style with plenty of energy food to keep you going! Dinners are generally eaten in hotels or nearby inns.

Dietary Requirements

Being vegetarian or having other dietary requirements is not usually a problem provided you let us know well in advance. If you know there are plenty of foods you cannot eat you may wish to bring extra snacks from home so you can top up your energy supply, or buy them as you go along. Please feel free to ask us for advice.

Trip Support

Discover Adventure Crew

Your trip will be led by experienced Discover Adventure leaders. Our leaders are selected for their experience in harsh wilderness environments, knowledge of travel in remote areas, friendliness and approachability, sense of humour and ability to safely and effectively deal with any situation that arises. They are also trained in expedition first-aid. You are in very safe hands with a Discover Adventure leader.

All our leaders are from the UK or other English-speaking countries. Most work for us on an ad-hoc basis and have ‘real’ jobs in-between trips! We never send our leaders to the same destination for months on end – we want them to be as enthusiastic about your trip as you are. The number of crew and support vehicles looking after you will depend on the final size of your group, but the team will be looking after every aspect of your trip whether that’s transporting your luggage, making your lunch or sorting out any mechanical problems. At Discover Adventure we pride ourselves on our high leader: cyclist ratio and believe it leads to greater trip enjoyment as well as excellent trip safety.


Support vehicles are with the group all of the time. All luggage and spares will be carried in them. Space is limited and hard-sided luggage is not suitable, so it is essential that your kit is packed in a soft sailing bag, rucksack or expedition kitbag. Ask us about our specially-designed low-cost kitbags if you don’t have one already. You should also bring a small daypack or large bumbag to carry for items needed during the day as you will not have access to your main luggage until the evening.

Trip Safety

Your safety, and that of the rest of the group, is our highest priority. Our trips are designed and planned with safety in mind. Your crew will be equipped with radios and emergency mobile phones, first-aid kits and other safety apparatus where necessary. They always have access to our 24-hour emergency back-up. Our leaders are responsible for safety on the trip, and will make any changes to the itinerary they deem necessary should local conditions dictate. Pre-trip administration – such as compulsory medical questionnaires and travel insurance – is all done with your safety in mind.

Preparing for the challenge

Cycling Information


The cycling is a mixture of steep climbs and sharp descents as the route undulates across the country.  Distances are challenging for the terrain, varying between 50 to 60 miles per day, and participants should make sure they are fit enough to manage these distances and climbs in all weathers.  This is not a ride which any cyclist should attempt without specific training. Traffic is light on most of the roads but when we pass through large towns we usually go through as a group.
We are always happy to talk through the trip in more detail with you if you are worried about your fitness at any stage.


We strongly recommend that you ride a road /racing bike (rather than a mountain bike) for this trip due to the long distances involved on well-surfaced roads. It’s really important that you ride the bike you have been training on so you are used to it. Although training in the gym is useful, there is no substitute for getting out into all weathers and really getting to know your bike – especially the range of your gears. However, Discover Adventure can provide hybrid or mountain bikes at extra cost if you wish.

Bike Repairs

Our support vehicles will carry a range of spares along with a full tool kit. However it is impossible for us to carry spares for every eventuality so it is vital that you check your own bike is in good working order before departure.
It is a condition of travel that you supply your own helmet and wear it at all times while cycling, with the straps done up.

Clothing & Equipment

We are travelling through varied terrain and could be exposed to bad weather at any time. The information below gives you an idea of the climate, but be prepared for all weathers and temperatures. Weather conditions can change quickly in the UK, especially the hillier regions we pass through. We provide you with a detailed packing kit-list on registration, as well as details on useful discounts you are entitled to as a Discover Adventure customer.


The weather should be generally good, though it can be changeable especially in when we are at height, where there is an increased chance of rain and strong winds. The prevailing wind direction will have more of an impact on the cycling difficulty than rain.

Fitness Levels

Our challenges attract people of all levels of experience and fitness, all ages and backgrounds. We expect all participants to train hard in advance to achieve this challenge, but we respect everyone’s limits. We design our challenges so that everyone can go at their own pace: this is not a race. For logistical and safety reasons we sometimes need to re-group, so the front-runners will find themselves waiting for the slower ones. Please relax, and remember that this is a team effort that enables people to achieve their personal goals and earn sponsorship.


We insist that you have had a tetanus injection in the last 10 years.

Worldwide Sustainable Tourism

Long before ‘Responsible Tourism’ became a recognised phrase, we designed and ran our trips to ensure they made minimum impact on the environment and a positive impact on the local communities we pass through.

Discover Adventure Projects

We are supporting a tree-planting project in Peru and a children’s home in Tanzania on a long-term basis. If you would like to ‘give something back’ please consider donating £5 to our projects when you sign up.

Carbon Offsetting

We encourage all our customers to offset emissions connected with their trip. You can offset at any time in the lead-up to departure by visiting Climate Care via our website and making a donation to a worthwhile project supported by them. Alternatively, if you wish to take more practical action in the UK you can volunteer for a day with TCV and work on an environmental project local to you. Work may include construction footpaths, dry stone walling, creating wildlife habitats or planting trees in your community. Volunteer today at or call 01302 388883.

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