A Scenic Cycling Route
A countryside ride through Middleham, Leyburn and Masham
For visitors looking to explore the Yorkshire Dales by bike, this beautiful countryside loop offers a memorable ride through historic villages, open farmland and rolling hills. The route connects Masham, Middleham, Leyburn and Thornton Steward, passing through some of the most scenic landscapes in Wensleydale.
Along the way, riders experience quiet country lanes, sweeping valley views and the unique character of Middleham — a town deeply connected to horse racing and equestrian culture.
Route Overview
Start: Masham Market Square
Distance: Approximately 24.5 miles
Difficulty: Moderate (some hills)
Estimated riding time: Around 2 hours without long stops
This circular route combines history, countryside views and classic Yorkshire villages, making it a rewarding ride for cyclists staying in the area.
Masham to Middleham
The ride begins in Masham, a traditional market town in North Yorkshire. Leaving the market square, the route follows quiet roads that climb gently out of the town, offering wide views across the River Ure valley and surrounding farmland.
As the road rises, the landscape shifts between pastureland and open fields before gradually descending towards Middleham.
Through Middleham and Its Castle
Entering Middleham, riders pass through a town closely tied to British horse racing. The streets often echo with the sound of horses being exercised from nearby training yards.
A short detour leads to Middleham Castle, once the childhood home of Richard III. The castle dates back to the 12th century and remains one of the most impressive historic landmarks in the Yorkshire Dales.
From here, the route continues out of town towards Leyburn, another charming market town known for its independent shops and cafés.
Leyburn and the Road to Harmby
Leaving Leyburn, the route turns towards the village of Harmby, where the countryside opens into gently rolling hills and quiet lanes.
This section of the ride offers some of the most peaceful stretches of road, passing fields, stone walls and small village churches typical of the Yorkshire Dales landscape.
Thornton Steward and the Return to Masham
Continuing through Spennithorne and Thornton Steward, the road eventually reconnects with the valley leading back towards Masham.
The final stretch follows the River Ure, bringing riders back to the market square where the ride began — an ideal place to stop for a coffee or a pint in one of Masham’s traditional pubs.
Cycling Near The Old Manse
For guests staying at The Old Manse in Middleham, this route offers a fantastic way to explore the surrounding countryside. Middleham sits almost perfectly along the loop, making it easy to join the ride directly from the village.
Cycling through this part of the Yorkshire Dales National Park reveals the landscapes, villages and traditions that make the region so special.
