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Road Cycling

Coast to Coast

Next Trip: 28th - 5th May 2024 Duration: 8 Days / 7 Nights

From £2,795 View Prices & Dates

Travel Planning & Advice

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Trip created by Harvey Downard
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Region: Multi-Location
Trip Type: Road Cycling
Accommodation: Deluxe
Max Group Size: 12
Confirmed: When 3 Traveller(s) Book
Deposit From: £698.75 £698.75


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All you need to know about your trip, this essential document is a must for all adventures.

Download Itinerary

With your knowledgeable Wilderness guide, enjoy some of the best road cycling in the UK as you ride coast to coast across England, pedalling through three of the country’s most breathtaking national parks.

On a trip that takes you along quiet backroads, up challenging climbs and down fast-flowing descents, relax into the melodic rhythm and peaceful joy that comes from spending time on a bike. As you wind your way west to east, cycle along world-class roads that were used in the Tour de France and the Road Cycling World Championships. Take a break from the saddle to refuel in charming cafes and cosy pubs, enjoying seasonable food and locally brewed beer. As dusk settles, relax each evening in carefully chosen and hand-picked accommodations, defined by their English charm and warm hospitality.

Need a bike? See our bike hire page for details.

Trip Highlights

  • Discover the diverse beauty of the English landscape as you pedal west to east, traversing three of the country's most stunning national parks.
  • Relish in magnificent climbs and thrilling descents as you ride along fantastic roads used in the Tour de France and Road Cycling World Championships.
  • Enjoy the best of English hospitality, from welcoming rural pubs to cycle-friendly cafes and award-winning restaurants.

Day by Day Itinerary

Day 1 - Whitehaven to Keswick

Arrive at Penrith Railway Station this morning and meet your Wilderness guide. A short transfer will take you to Whitehaven, situated on the west coast of Cumbria, to start your Coast to Coast adventure. After a mellow morning of riding, enjoy a cafe lunch before heading deep into the Lakeland Fells via the Buttermere valley. The main climb of today, Newlands Pass, soon begins and winds its way through increasingly dramatic scenery. From the top, take in the spectacular views before descending into the valley to reach your cosy overnight stop in the pretty town of Keswick. (L, D)

Ride details: 51 km/32 miles | 801 m/2,628 ft elevation gain

Day 2 - Keswick to Ravenstonedale

As the morning mist lifts from the fields, ride along a lovely cycleway with the impressive mountain of Blencathra stretching high into the sky ahead. After a mid-morning stop in the charming village of Greystoke, leave the Lake District National Park behind and ride into the lush greenery of Eden Valley. Pedal along the quiet roads to a traditional pub where we can take a break for a hearty lunch. Continue riding this afternoon through Great Asby Scar Nature Reserve, stopping at a local luxury chocolate shop, before descending into the picturesque village of Ravenstonedale for a warm welcome and a delicious seasonal dinner. (B, L, D)

Ride details: 82 km/51 miles | 1,090 m/3,580 ft elevation gain

Day 3 - Deep into the Dales

After a relaxed breakfast, jump in with your guide for a short, scenic transfer into the heart of the Yorkshire Dales. An ancient landscape of ribboned glens, heathery hills and rolling fields bounded by dry stone walls, the Dales offers some fantastic road cycling. Clipped in and zipped up – set off from the historic village of Hawes to explore some of the most beautiful roads in the region. Along the way, take the opportunity to stop at an engaging heritage centre to learn about the history of the local area and enjoy a hot drink and a slice of cake. Back on the bikes, enjoy some great climbs and floaty descents before riding back to Ravenstonedale with time to relax in your charming accommodation before dinner. (B, L)

Ride details: 50 km/31 miles | 660 m/2,165 ft elevation gain

Day 4 - Through the Yorkshire Dales

Today, experience the pastoral beauty of the Yorkshire Dales National Park as you ride towards Masham. Spend the morning cycling along leafy lanes, your legs finding that happy rhythm that comes from their steady spinning. An impressive road from the village of Ravenstonedale gives way to sweeping moors and arching skies for some of the most enjoyable riding of the whole trip. Cheeks rosy, cruise the length of the Wensleydale Valley on roads used in the Tour de France. On the way, take the opportunity to stop and visit the impressive 14th century Castle Bolton before arriving in the attractive market town of Masham. (B, L, D)

Ride details: 73 km/45 miles | 720 m/2,360 ft elevation gain

Day 5 - Exploring the Yorkshire Dales

Roll out into the silky morning light for a stunning circular ride that takes you past lofty reservoirs and through the rolling valley of Nidderdale. With some climbs and fast, flowy descents, this is sure to be a memorable day. As you pedal chat with your guide about the region’s topography, which has been sculpted, scoured and shaped over many millennia by ice. Soak up the views, as you cycle from moorlands to lush valley bottoms, listening for the bubbling call of the curlew and the electronic peewit-peewit of lapwings. The satisfying crunch of gravel indicates your arrival back in Masham this afternoon, with time to head to the local brewery for a freshly poured pint and a well-earned dinner. (B, L, D)

Ride details: 60 km/37 miles | 920 m/3,020 ft elevation gain

Day 6 - Masham to Great Ayton

Depart the friendly town of Masham this morning to traverse the gently undulating Vale of Mowbray. After a wonderful pedal to Osmotherley, a village nestled in the Hambleton Hills, leave your helmets on your handlebars and enjoy lunch. Afterwards, feeling relaxed and well-fuelled, head into the North York Moors National Park. Evocative as it is wild, the National Park encompasses a fascinating mixture of flora and fauna, so make sure to keep an eye out for roe deer, brown hare, kestrels, sparrowhawks and peregrines. This afternoon, gradually make your way north, arriving in the golden hours of early evening at a quintessential country pub tucked at the foot of Roseberry Topping hill. (B, L, D)

Ride details: 76 km/47 miles | 640 m/2,100 ft elevation gain

Day 7 - Rievaulx to Great Ayton

Head out this morning on a ride that explores the beautiful and diverse landscape of the North York Moors National Park. A short transfer takes you to the spectacular Rievaulx Abbey – its evocative ruins and fascinating museum telling the story of the rise and fall of the first Cistercian abbey in northern England. After taking some time to explore, set off on a route that winds its way through pretty valleys dotted with ancient abbeys and historic castles. A challenging, steep climb takes you past the iconic Kilburn white horse, carved impressively into the hillside, and over Sutton Bank – a spot that sports some of the finest views in England. Gorgeous scenery follows as you pedal back to your cosy accommodation for dinner this evening. (B, L, D)

Ride details: 81 km/50 miles | 1,139 m/3,736 ft elevation gain

Day 8 - Great Ayton to Robin Hood’s Bay

Your final day of riding threads its way through the North York Moors to reach the east coast of England and your sea-soaked finish line. A brilliant route characterised by climbing high and dropping low, it’s sure to be an exciting and memorable day in the saddle. After a steady morning pedal to warm up the legs, a climb to Commondale takes you to the highest point of the day. Take a break in Castleton, a pretty village tucked amongst the pastoral beauty of the Upper Esk Valley, before descending into Robin Hoods Bay and the sparking white-capped waves of the North Sea. Celebrate a fantastic trip with lunch by the sea before being transferred to York Railway Station for your onward travel. (B, L)

Ride details: 55 km/34 miles | 785 m/2,575 ft elevation gain

Road Cycling
Coast to Coast

To download a PDF copy of our Trip Itinerary, containing full details about this holiday, please complete the form below:

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Trip Dates & Prices

Trip Dates for 2024AvailabilityStatusPriceBook
28th Apr - 5th May 202412 place(s) leftUNCONFIRMED£2,795Book Now
16th Jun - 23rd Jun 202412 place(s) leftUNCONFIRMED£2,795Book Now
14th Jul - 21st Jul 20249 place(s) leftCONFIRMED£2,795Book Now
25th Aug - 1st Sep 202412 place(s) leftUNCONFIRMED£2,795Book Now

Trip Details

Accommodation Read More

Our accommodation partners are carefully chosen according to a number of factors such as their charming locations, very good facilities and reputation for providing excellent hospitality. Accommodation is in a choice of double or twin rooms with ensuite facilities.

Single Rooms

For solo travellers: Accommodation is based on sharing a twin room with another solo traveller of the same gender. A limited number of rooms for single occupancy are available on a first come first served basis, subject to a single supplement of £425. Please enquire about availability.

Meals Read More

On this trip all meals are included from lunch on day 1 to lunch on day 8, apart from dinner on day 3. Your guide will let you know the options for dinner on day 3 and help you make the necessary reservations and then they’ll take the evening off. Included dinners are two courses as standard and special dietary requirements can be catered for.

Inclusions Read More
  • 8 days of professional guiding with a lead guide plus assistant guide/support driver
  • 7 nights accommodation in hotels and inns handpicked by us
  • All meals from lunch on your day of arrival, to breakfast on the final day, except for dinner on day 3 (Meals included indicated as B=Breakfast, L=Lunch, D=Dinner)
  • Vehicle transport throughout, including ride support and luggage transfers. Starting in
  • Penrith and finishing in York.
  • Entrance and admission fees, as stated in the itinerary
  • Ride snacks and drinks throughout your trip
Trip Grading Read More

Blue Graded 4-6

Blue graded trips are suitable for people with a good level of bike fitness, who regularly enjoy cycling and may have joined a multi-day cycle holiday before.

Distances each day will be between 35 and 45 miles, cycling at around 12/13mph. Each day will encompass rolling and hilly terrain, with notable climbs most days. Some of these climbs will be more testing, and some riders may opt to ride in the support vehicle. Some climbs are also followed by exciting descents. We will be in the saddle for 5 to 7 hours each day plus the odd longer day. There is also time each day for breaks and lunches, plus some visits to sites of interest.

Travel Read More

You will be met by your Wilderness England Guide at Penrith Railway Station at 10:00 am on Day 1 of your trip. The trip will conclude at York Railway Station at 4:00 pm on the final day of the trip.

Bike Hire / Bringing Your Own Bike Read More
Bike Hire

We have an excellent fleet of bikes available to hire u2013 including road bikes, hybrid bikes and E-bikes.
Find Out More

Bring Your Own Bike

You are also more than welcome to bring your own bike.

If you choose to do so, please ensure it’s in excellent working condition and has been recently serviced u2013 either by you or by a reputable bike shop.

In addition, please bring the following:

  • Multi-tool, including a chain tool
  • Mini pump and/or CO2 canisters
  • Two spare tubes and a puncture repair kit

Because we will need to load your bike onto one of our trailers, please ensure that:

  • Your rear wheel is clear of any obstructions; including lights, mudguard or panniers
  • Your tyres are no wider than 45mm

Due to the nature of our trips, we are unfortunately unable to carry bike boxes or bags with us, so please make prior arrangements if necessary.

If you have any questions at all, don’t hesitate to get in touch. Our friendly and knowledgable sales team are always delighted to answer any queries you may have.

Photo Gallery

Make This Trip Private

Fancy this trip just for your group? Get together with family and friends spend quality time exploring wild places. A private trip allows you to benefit from all the features of the group departure, including hand-picked accommodation and expert local guides but with the advantage of the flexibility to tailor the days to your group. Make the trip more or less challenging depending on your experience or choose to add in some optional extras like castle or distillery visits depending on your interests. The price of a private trip will depend on the number of travellers in your group. Let us know your prefered departure date and we'll take care of the rest.

Speak to an Expert

Chris Page

Our friendly office team hail from across the world but share a passion for the outdoor and wild spaces of England. We are committed to providing you with the best customer service and are more than happy to chat through options and provide help and advice. Get in touch to find your perfect adventure.

Ask Chris a Question

Meet Your Guide

Difficulty Grades Explained

Blue Graded Road Cycling Holidays 4-6

Blue graded trips are suitable for people with a good level of bike fitness, who regularly enjoy cycling and may have joined a multi-day cycle holiday before.

Distances each day will be between 35 – 45 miles, cycling at around 12/13mph. Each day will be rolling and hilly terrain and there will be notable climbs most days. Some of these will be more testing and some riders may opt to push or ride in the support vehicle. Some climbs are also followed by exciting descents. We will be in the saddle for 5 – 7 hours each day plus the odd longer day. There is also time each day for breaks and lunches, plus some visits to sites of interest.

Compare road cycling grades

Our holidays reviewed
in your own words

This trip was amazing, we got to see so much of the 5 countries in so little time. The sites and locations that were mapped out were perfect. A rest day in Dublin is the perfect city to explore and find good food. The guides were knowledgeable and thoughtful, and made the trip very easy, all we had to do was bike and show up to dinner! Absolutely awesome experience.

Daniel Patton
Road Cycling - The Five Countries
Reviewed on 29/08/2022

Rated 4.95 out of 5 based on 716 reviews

Read More Reviews

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