If you‘re traveling by train, you’ll arrive at Thirsk station, where a friendly representative will meet you and transfer you to Helmsley for your welcome meeting and bike fitting.

For those driving, simply make your way to the hotel in Helmsley, and one of our representatives will meet you the following morning. You are then free to spend the day exploring this wonderful market town with its small, cobbled streets and its quaint shops and cafes. Helmsley Castle and nearby Duncombe Park Estate are also well worth a visit. There are numerous places to eat in the town in the evening.

• Meals: Breakfast
• Ascent: 415 or 780 Metres Approx

This morning you’ll have a gentle start as you ride out of Helmsley, and will soon be on quiet roads and in the beautiful Yorkshire countryside. You will get your first taste of the North York Moors soon after passing the village of Gillamoor, with stunning views over the moorlands to the north, as a short steep climb then descent take you to Hutton-le-Hole. This quaint village, scattered with beautiful stone cottages and home to the Ryedale Folk Museum, as well as a few pubs and cafes, is a great place to take your first coffee break of the day. From here, the route takes you high up on to the North York Moors; the roads are very exposed from here so if there are strong winds or poor visibility, or if your legs aren’t quite feeling up to the climbs of the first day, we recommend taking the shorter route through Lastingham and on to your hotel in Pickering.

However, if you‘re feeling up to the challenge and the weather’s looking good, we recommend taking the standard, longer route up the long gradual climb to Blakey Ridge to the highest point of the day (and in fact the highest point of the entire trip!) to just over 400m (1300ft). You reach the top at Millennium Stone Viewpoint which boasts extensive views over the spectacular moorland. A very welcome descent then takes you into Rosedale Abbey where there are a few cafes to take a well-earned lunch.

From here, undulating roads, including a few steep climbs then a long descent, take you to your accommodation. Pickering is a lovely market town to discover, with plenty of restaurants, cafes and shops, or you could just relax and unwind in your hotel, knowing the longest day of the trip is behind you! If you have time, Pickering Castle is a short walk or ride away, and the North Yorkshire Moors Railway station in the centre of the town is worth a visit; if you‘re lucky, you’ll catch the impressive steam train pull in to the platform, but even if not, the 1930’s themed station is a must-see!

• Meals: Breakfast
• Ascent: 495 Metres Approx

After your venture into the North York Moors yesterday, today’s riding takes you into a very different, more wooded landscape. After a few miles of easy riding through farmland to get the legs warmed up, you take a scenic off-road gravel track through Dalby Forest, a mountain biker’s paradise! Keep an eye out for riders in full face-helmets and body armour, but don’t worry, our route takes you away from the technical graded trails as you climb through the trees on the very pleasant Forest Drive, before descending on road to the River Derwent.

The route continues along quiet roads with a few cheeky climbs along the way, before you reach the outskirts of Scarborough and the hustle and bustle of this busy seaside town. Your accommodation this evening is just a stone’s throw from the beach, so after your ride, you can take a stroll on the promenade to Scarborough castle and catch the funicular back to the top of the hill before going out for food in one of the various restaurants in the town centre this evening.

• Meals: Breakfast
• Ascent: 470 Metres Approx

Today’s ride is a beautiful route which takes you along Yorkshire’s ‘Dinosaur Coast‘, a second favourite of fossil enthusiasts after the Jurassic Coast. You take a scenic route out of Scarborough along the coastal road, before cutting inland to follow the course of an old railway line all the way to Whitby. Known as the ‘Cinder Track’ due to the cinder surface, which was used as ballast for the railway tracks, this popular route is still unsurfaced in places, so please take care, and note this section of the route is not suitable for road bikes.

After a long and gradual climb through the trees, you will see the sea again as you emerge at the dramatic clifftops at Ravenscar. This intriguing village was built in the late Victorian period, with the ambition of becoming a seaside resort to rival Scarborough and Whitby. However, it didn’t quite catch on and all that remains, are a handful of houses and a cafe in the old railway station.

Back on the old railway path, your next stop is the picturesque village of Robin Hood’s Bay. Whilst this vibrant little fishing village is well worth a stop-off, we suggest you lock your bikes at the top of the hill before descending the steep cobbled streets to the harbour on foot, as it’s a very steep and busy climb back to the top again! The final stint of the day takes you down to Whitby, synonymous with Bram Stoker’s Dracula, which was set in the iconic Whitby Abbey at the top of the 199 steps. There is plenty to see and do in this beautiful coastal town, but getting fish & chips here is an absolute must – your only difficulty will be deciding which chippy to choose!

• Meals: Breakfast
• Ascent: 745 Metres Approx

Today, you will say goodbye to the coast as you head west along the River Esk and back up into the North York Moors, passing through the quaint villages of Egton, Castleton and Commondale. A steep morning climb takes you up to Aislaby after a few miles, before you pedal along quiet single-track lanes with stunning views over the Esk valley.

At just over halfway, Danby Lodge National Park Centre is a perfect setting for some coffee and cake before you tackle a series of short, steep climbs and descents (some of which with gradients of up to 20%), but you are rewarded with beautiful views over the North York Moors and glimpses of Rosebury Topping – the distinctive conical hill on the northern edge of the North York Moors. You’ll be glad to reach the village of Kildale, around 5 miles (8km) from the end, as the road takes you downhill from here into the village of Great Ayton, and your accommodation for the evening.

• Meals: Breakfast
• Ascent: 725 Metres Approx

You’ll likely want an early breakfast this morning as you prepare for another hilly day in the saddle today. The morning’s ride is relatively gentle, as you skirt around the eastern edge of the Cleveland Hills to Swainby, which is a nice place for coffee, and a good idea to top up on some supplies for a picnic lunch, as there aren’t many shops or cafes beyond here.

Hopefully your legs will be accustomed to North Yorkshire’s steep climbs by the time you get to the 20% climb to Cod Beck Reservoir, but it’s worth it for the scenic views! The final 15 mile (25km) section of the holiday is probably the toughest, as there are several steep climbs and sharp descents on the scenic single track roads which take you around Osmotherley Moor, Snilesworth Moor and Hawnby Moor.

Your final stop before the end should be Rievaulx Abbey – a 12th Century abbey ruin hidden in the River Rye Valley. A final climb then descent takes you into Helmsley, and with over 140 miles / 225km in your legs, you can celebrate with a pint and a meal, then a good night’s rest before heading home tomorrow.

• Meals: Breakfast

After your final night in Helmsley, you can set off on your journey home. A transfer back to Thirsk station will be provided if you are travelling by train or, if driving, you can leave directly from Helmsley after checking out from your hotel.