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Road cycling routes
United Kingdom
England
Yorkshire And The Humber
North Yorkshire
Ryedale

Rosedale East Side

The best road cycling routes around Rosedale East Side

4.6

(33)

1,582

riders

62

rides

Road cycling around Rosedale East Side, nestled within the North York Moors National Park, features diverse landscapes characterized by vast heather moorland and deep valleys. The region offers challenging ascents, such as the renowned Rosedale Chimney Bank, alongside more gentle routes following historic railway lines. These paths often provide views across the dale and surrounding moors. The terrain includes both paved surfaces and some unpaved segments, catering to varied road cycling preferences.

Best road cycling routes around Rosedale East Side

Last updated: May 20, 2026

2

riders

#1.

Rosedale Abbey to Pickering — North York Moors Cycleway

18.6km

00:49

160m

260m

Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

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Easy

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate
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Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate

Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.

Hard

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate
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Tips from the Community

JakobusPilger
March 21, 2026, Young Ralph Cross

Each of the sacred monuments that you repeatedly encounter – despite all the differences in their external design – has a common concern: The cross that rises here not only wants to attract the viewer's gaze, but – and this is primarily – to make him think of God. Not only in theological books, but even in secular literature, God's voice is often represented, and this is even often the case in crime novels. For example, Ellis Peters set the series of novels about the Benedictine 'Brother Cadfael', which is set in 12th-century England, in the surroundings of a monastery. In "The Virgin in the Ice" it says: "And yet life, clinging to faith, the tenacious struggle with fate had to go on, the land had to be cultivated year in, year out. Plough and harrow must not rest, and one had to take care of sowing and harvesting the fruits of the earth as much as here, in the monastery and church, of sowing and harvesting souls." I wish the viewer here in front of the cross a good thought for his soul.

Translated by Google

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Stuart Wilcock
December 21, 2025, Whitby Harbour

Whitby Harbour is a historic and bustling port at the mouth of the River Esk in North Yorkshire, offering a various attractions, shops, and dining places.

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Head on out to either of the 2 main piers and experience an epic sunrise or sunset!

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Nice spot to fuel up with a view. Cakes simple sandwiches and drinks. Friendly staff

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Graze on the Green cafe, excellent food

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RichD
September 7, 2024, Fat Betty (White Cross)

The monument includes a standing cross, Listed Grade II, used as a boundary marker and known as Fat Betty or the White Cross. It stands on Danby Moor at the junction of three parishes whose boundaries were fixed during the medieval period. It is on the north side of a minor road to Rosedale 510m to the east of the cross known as Young Ralph. On the north side of the base is the date 1919 cut in the stone. On the west side is an inscription BS IB 1953. Neither inscription bears on a date for this monument. There is also an OS benchmark on the west face. The cross has been repeatedly whitewashed over the years in accordance with the practice of the Downe Estate on which it stands. The cross has been set up on Danby Moor to mark the meeting of the old parishes of Danby, Westerdale and Rosedale. It also marks the side of an old road down to Rosedale from the cross called Young Ralph. The road is mentioned in a 13th century charter from Guisborough.

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RichD
September 7, 2024, Young Ralph Cross

Wayside crosses are one of several types of Christian cross erected during the medieval period, mostly from the 9th to 15th centuries AD. In addition to serving the function of reiterating and reinforcing the Christian faith amongst those who passed the cross and of reassuring the traveller, wayside crosses often fulfilled a role as waymarkers, especially in difficult and otherwise unmarked terrain. The crosses might be on regularly used routes linking ordinary settlements or on routes having a more specifically religious function, including those providing access to religious sites for parishioners and funeral processions, or marking long-distance routes frequented on pilgrimages. Over 350 wayside crosses are known nationally, concentrated in south west England throughout Cornwall and on Dartmoor where they form the commonest type of stone cross. A small group also occurs on the North York Moors. The wayside cross and boundary marker known as Young Ralph survive complete even though previously broken and repaired. The cross marks the highest point on the old road from Keldholme in the south of the moors to Castleton in the north. It also marks the boundary of the Wapentake of Pickering Lyth. It has been adopted as the symbol of the North York Moors National Park and has been a listed monument since 1938.

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Free e-bike charging and repari station.

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Frequently Asked Questions

How many road cycling routes are available in Rosedale East Side?

Rosedale East Side offers a wide selection of road cycling routes, with over 60 options available. These routes cater to various skill levels, from easy rides to more challenging ascents.

What kind of terrain can I expect on road cycling routes in Rosedale East Side?

The terrain in Rosedale East Side is diverse, featuring expansive heather moorland and deep valleys. You'll encounter challenging ascents like the renowned Rosedale Chimney Bank, as well as more gentle routes that follow historic railway lines. Most routes are on paved surfaces, but some may include unpaved segments.

Are there options for less experienced road cyclists in Rosedale East Side?

Yes, Rosedale East Side has options suitable for less experienced road cyclists. There are 12 easy routes available, such as the Rosedale Abbey to Pickering — North York Moors Cycleway, which offers a relatively flat ride connecting Rosedale Abbey to Pickering.

What are the most challenging road cycling routes in the area?

For experienced cyclists seeking a challenge, Rosedale East Side is famous for formidable ascents like Rosedale Chimney Bank, known for its steep gradients. There are 17 difficult routes in the area, including the Blakey Bank Summit – Whitby Harbour loop from The Lion Inn, which covers 46.6 miles with significant elevation gain.

What is the best time of year to go road cycling in Rosedale East Side?

The North York Moors, including Rosedale East Side, are beautiful year-round. However, for road cycling, late spring to early autumn (May to October) generally offers the most favorable weather conditions with milder temperatures and less chance of adverse weather, making for a more enjoyable experience on the exposed moorland routes.

Are there any notable natural attractions to see along the road cycling routes?

Yes, the region boasts several natural attractions. You might encounter the impressive Mallyan Spout Waterfall, the tallest waterfall in the North York Moors, or enjoy views from Round Hill Summit, the highest point of Urra Moor, on some routes.

What historical sites can I explore while road cycling in Rosedale East Side?

The area is rich in history. You can see the crumbling Bank Top Iron Kilns, a testament to the Victorian ironstone mining industry, or pass by the romantic Beggar's Bridge across the River Esk. These sites offer a glimpse into the region's past.

Are there any scenic viewpoints on the road cycling routes?

Many road cycling routes in Rosedale East Side offer breathtaking views across the dale and surrounding moors. Keep an eye out for spots like Simon Howe Bronze Age Cairn or Dundale Griff, which provide excellent panoramic vistas of the landscape.

Are there any circular road cycling routes in Rosedale East Side?

Yes, there are several circular road cycling routes. An example is the Keys Beck Road – Pry Hills Lane loop from Rosedale Abbey, a moderate 31.1-mile path that takes you through the moorland landscape and back to your starting point.

What do other road cyclists enjoy most about road cycling in Rosedale East Side?

The area is highly rated by the komoot community, with an average score of 4.6 stars from over 30 reviews. Cyclists often praise the diverse landscapes, from challenging moorland climbs to scenic routes along historic railway lines, and the stunning views across the dale.

Are there any family-friendly road cycling options in Rosedale East Side?

While many routes feature challenging gradients, some sections of the old Rosedale Railway have been upgraded into bridleways, offering gentler, comfortable tracks with beautiful moorland views. These can be suitable for families looking for a less strenuous ride, though specific family-focused road routes might be limited due to the general challenging nature of the area.

Where can I find amenities like cafes or pubs near the road cycling routes?

Rosedale Abbey village serves as a central point in the valley and offers amenities. Additionally, villages like Hutton-le-Hole, considered one of the prettiest in the North York Moors, provide access to local cafes and pubs, perfect for a break during your ride.

Is parking available for road cyclists in Rosedale East Side?

Yes, parking is generally available in and around the villages within Rosedale East Side, such as Rosedale Abbey. It's advisable to check specific starting points of routes for designated parking areas to ensure convenience.

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