4.6
(82)
5,016
riders
12
rides
Road cycling around Wingerworth offers diverse routes through Derbyshire's scenic countryside, catering to various fitness levels. The area features well-paved surfaces, rolling hills, and accessible trails, providing a range of experiences from leisurely rides to more challenging excursions. Cyclists can explore landscapes characterized by woodlands, reservoirs, and open farmland, with routes often including significant elevation changes. The region's geography makes it suitable for exploring both natural features and historical sites by road bike.
Last updated: July 14, 2026
4.0
(1)
58
riders
36.6km
02:03
600m
600m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
25
riders
20.0km
01:09
320m
320m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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10
riders
43.6km
02:10
530m
530m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
8
riders
27.1km
01:24
350m
350m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
6
riders
15.3km
00:49
210m
210m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
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Hiking down the a road for a stunning view of Ogston Reservoir from Ashover
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Ashover Rock is a mile hike up from Ashover and offers superb views over Derbyshire
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beautiful peaceful spot with car park and bird hide
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Stubbing Pond's history is connected to the industrial past of the Wingerworth area. The pond was created as a source of water power for various activities, including the operation of a smithy. The dam for Stubbing Great Pond was constructed around 1700. From the pond, one can see Stubbing Court, the ancestral home of the Hunloke family.
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Greart Climb from Beeley. Road is closed to traffic due to a landslip but you can ride up on a bike after negotiating the barriers.
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Wingerworth offers a diverse selection of over 10 road cycling routes, catering to various fitness levels. These routes explore the scenic Derbyshire countryside, featuring well-paved surfaces and rolling hills.
Road cycling around Wingerworth is characterized by rolling hills, woodlands, and reservoir views. Routes often include significant elevation changes, with some moderate trails featuring over 500 meters of ascent, such as the Beeley Moor Summit – Stubbing Pond Boathouse loop from Wingerworth.
Yes, Wingerworth offers routes suitable for beginners and those looking for an easier ride. An example is the Steep Lane – Stubbing Pond Boathouse loop from Wingerworth, which is rated as easy and covers about 15.3 kilometers with manageable elevation.
Absolutely. The broader Derbyshire area, including routes around Wingerworth, is known for its challenging climbs. For instance, the Beeley Moor Summit – Stubbing Pond Boathouse loop from Wingerworth features over 600 meters of elevation gain, providing a good test for experienced cyclists.
Cyclists can enjoy stunning natural beauty, including the three Linacre Reservoirs surrounded by woodlands, and the diverse habitats of The Avenue Washlands. Routes like the Ogston Reservoir – View of Ogston Reservoir loop from Wingerworth offer picturesque views of the reservoir and surrounding countryside.
Yes, the region boasts several historical sites. You can find landmarks like the ancient Nine Ladies Stone Circle, the impressive Crich Stand (Sherwood Foresters Regiment Memorial), and the distinctive Ashover Rock (The Fabrick), which are often incorporated into cycling routes.
Many of the road cycling routes around Wingerworth are designed as loops, allowing you to start and finish in the same location. Examples include the Ashover Rock (The Fabrick) – Britton Wood loop from Wingerworth and the Ogston Reservoir – View of Ogston Reservoir loop from Wingerworth.
While specific parking areas for cyclists are not detailed, Wingerworth and its surrounding villages offer various public parking options. Many routes start from Wingerworth itself, suggesting local parking would be available. For routes extending towards Chesterfield, accessing the Five Pits Trail from Chesterfield Railway Station could be an option.
Wingerworth has local bus services connecting it to nearby towns. For broader access, Chesterfield Railway Station provides a link to the Five Pits Trail, which offers a traffic-free cycling experience and can be a starting point for exploring the wider area.
The road cycling routes in Wingerworth are highly rated by the komoot community, with an average score of 4.6 stars from over 90 reviews. Cyclists frequently praise the diverse landscapes, well-paved surfaces, and the variety of routes that cater to different skill levels, from leisurely rides to more demanding challenges.
Yes, the nearby Five Pits Trail offers a fantastic traffic-free cycling experience. This 5.5-mile (extending to 7.5 miles with a loop) route is built on a former railway line and is accessible from Chesterfield Railway Station, winding through scenic countryside and former railway lines.
Road cycling in Wingerworth is popular throughout the warmer months, particularly in May and July, when the weather is generally more favorable. Spring offers the added beauty of bluebells in the woodlands around Linacre Reservoirs, while autumn provides vibrant foliage.


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