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Road cycling routes
United Kingdom
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Yorkshire And The Humber
North Yorkshire
Richmondshire

Middleham

The best road cycling routes around Middleham

4.3

(35)

1,790

riders

17

rides

Road cycling around Middleham, situated within the Yorkshire Dales National Park, features a diverse landscape of rolling green hills, valleys, and stretches of Pennine moorland. The region is characterized by its varied terrain, offering both undulating single-track roads and significant elevation gains. Cyclists can navigate through Wensleydale, known for its scenic countryside, and encounter historical landmarks such as Middleham Castle.

Best road cycling routes around Middleham

  • The most popular road cycling route is Oxnop to Crow Trees Descent – Grinton…

Last updated: April 27, 2026

5.0

(8)

332

riders

#1.

Oxnop to Crow Trees Descent – Grinton Moor loop from Middleham

71.0km

03:28

1,050m

1,050m

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

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Hard

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

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

Hard

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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Popular around Middleham

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Tips from the Community

Mark Halliday
May 3, 2026, Park Rash Climb from Kettlewell

Brutal. Go around the wrong side of the road and plead forgiveness to the motorists (good luck with that). Take care coming down. With lots of gravel on the road

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RichD
February 15, 2026, Reeth Village Green

One of the largest and most open village greens in the Yorkshire Dales, historically used for markets, fairs, and livestock trading — the social heart of Swaledale long before tourism arrived. The green’s broad, triangular shape reflects its medieval origins as a common grazing and gathering space. Plenty of parking around the village green, but having arrived at 7am in winter for a hike and finding them all full, I suspect other times of the year will be even more difficult to secure a space.

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RichD
February 15, 2026, Grinton Moor

A classic stretch of high Pennine moorland, shaped by centuries of lead‑mining, with old hushes, spoil heaps, and trackways still etched into the heather. The moor forms part of the Reeth–Grinton–Harkerside upland block, giving wide, open views over Swaledale. Spectacular under a layer of snow in winter.

1

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📸 Anna
September 3, 2025, Reeth Village Green

A wonderful village on the Coast to Coast Path. There are plenty of places to stay around the village green. The village youth play football on the lawn, including the very young ones. Very nice!

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Gears 34 x 34 . Keep to outside of bend. Pace yourself

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Fantastic loop from Hawes to Muker then Cross tops to Askridge then steady back to Hawes . The climbs are tough but an awesome ride

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Masham Bridge crosses the River Ure just north of the small town on the A6108. It is an arch bridge and was opened in 1754 on The Avenue, Masham.

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Frequently Asked Questions

How many road cycling routes are available around Middleham?

There are over 15 dedicated road cycling routes around Middleham, catering to various preferences and fitness levels. These routes explore the diverse landscapes of Wensleydale and the surrounding Yorkshire Dales.

What kind of terrain can I expect on road cycling routes in Middleham?

Road cycling around Middleham offers a diverse mix of terrain. You'll encounter rolling green hills and valleys, as well as stretches of challenging Pennine moorland. The routes feature undulating single-track roads and significant elevation gains, often on mostly well-paved surfaces, providing both sweeping descents and 'thigh-burning inclines'.

Are there road cycling routes suitable for different fitness levels in Middleham?

Yes, Middleham offers routes for various abilities. You can find 5 easy routes for a more relaxed ride, 7 moderate routes for those looking for a bit more challenge, and 5 difficult routes for experienced cyclists seeking significant elevation gains and longer distances.

What are some notable landmarks or historical sites I might see along the road cycling routes?

Many routes pass by significant historical landmarks. You can cycle past the impressive ruins of Middleham Castle, known as 'The Windsor of the North' and childhood home of Richard III. Some routes also take you near the ruins of Jervaulx Abbey or the old Norman motte and bailey site of William's Hill, offering a glimpse into the region's rich history.

Can I find scenic viewpoints on the road cycling routes around Middleham?

Absolutely. The region is renowned for its stunning landscapes. Routes venturing towards areas like Grinton Moor offer expansive views over Swaledale and classic stretches of high Pennine moorland. The general topography of rolling countryside provides numerous opportunities for vast surrounding landscapes and picturesque vistas.

Are there any natural features or attractions to see while road cycling?

Yes, the routes often traverse beautiful natural settings. You'll experience the tranquil beauty of the Yorkshire Dales National Park, characterized by its 'rolling green and gray' hills. Some routes pass by rivers like the Cover and Ure, and you can also find natural monuments such as Aysgarth Lower Falls, Aysgarth Middle Falls, and Aysgarth Upper Falls, which are popular highlights in the area.

What do other road cyclists think about the routes in Middleham?

The road cycling routes in Middleham are highly regarded by the komoot community, holding an average rating of 4.6 stars from over 40 reviews. Cyclists often praise the varied terrain, the stunning Dales scenery, and the well-maintained surfaces that make for an enjoyable ride.

Are there any circular road cycling routes available from Middleham?

Yes, many of the road cycling routes around Middleham are designed as loops, allowing you to start and finish in the same location. Examples include the challenging Oxnop to Crow Trees Descent – Grinton Moor loop and the scenic Kidstones Pass – Kettlewell Village loop, both offering comprehensive tours of the local landscape.

Where can I find refreshments or places to rest along the routes?

The routes frequently pass through charming Dales villages, which often have local pubs and cafes where you can stop for refreshments. Middleham itself offers options, and villages like Kettlewell, Masham, and Reeth, which are featured on various routes, provide opportunities to experience local culture and take a break.

What is the best time of year for road cycling in Middleham?

The Yorkshire Dales offer beautiful cycling conditions throughout much of the year. Spring and summer provide lush green landscapes and generally milder weather, while autumn brings stunning colors. Some routes, particularly those on high Pennine moorland, can be spectacular even in winter, though conditions may be more challenging.

Are there any routes that incorporate parts of the former Tour de France route?

Yes, the region's reputation for cycling has been enhanced by events like the Tour de France. Some routes, such as those designed as 'Wensleydale Castles' and 'Coverdale Abbey' rides, specifically incorporate sections that were part of the former Tour de France route, offering a taste of professional cycling challenges.

What is the longest road cycling route available from Middleham?

One of the longer and more challenging routes is the Oxnop to Crow Trees Descent – Grinton Moor loop, which covers approximately 71 kilometers (44.1 miles) and features over 1000 meters of elevation gain, traversing classic Pennine moorland.

Is there a route that explores the Wensleydale area specifically?

Yes, the Kidstones Pass – Kettlewell Village loop is an excellent option for exploring the heart of Wensleydale. This route winds through the scenic countryside, featuring rolling hills and passing through charming Dales villages, offering a true taste of the dale.

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