Grassmoor, Hasland And Winswick
Grassmoor, Hasland And Winswick
4.5
(66)
3,828
riders
329
rides
Road cycling routes around Grassmoor, Hasland And Winswick traverse a landscape shaped by former industrial heritage, now reclaimed into green spaces and multi-use trails. The area features a network of paths along old railway lines and tranquil canal paths, offering mostly paved or well-surfaced routes with gentle gradients. Cyclists will encounter diverse scenery, including open meadows, woodlands, and a series of artificial lakes and wetland reserves. This blend of rural tranquility and accessible routes caters to various fitness levels.
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.
12
riders
44.7km
02:14
500m
500m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

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9
riders
23.3km
01:06
240m
240m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
7
riders
46.5km
02:17
540m
540m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
7
riders
21.1km
01:00
210m
210m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
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a nice climb and generally traffic free as it's closed forever
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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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The area offers a diverse range of road cycling routes, many of which utilize former railway lines and tranquil canal paths. These often provide mostly paved or well-surfaced routes with gentle gradients. You'll find a blend of rural tranquility, reclaimed colliery landscapes, open meadows, woodlands, and scenic water features like lakes and wetland reserves. The network caters to various fitness levels, from easy rides to more challenging excursions.
There are over 370 road cycling routes available around Grassmoor, Hasland, and Winswick. This includes a wide selection of easy, moderate, and difficult routes to suit different preferences and skill levels.
Yes, the region is well-suited for beginners and families, particularly due to the transformation of old railway lines and canal paths into multi-use trails. These routes, like sections of the Five Pits Trail, typically offer gentle gradients and well-surfaced paths, making them accessible for all skill levels. There are 71 easy routes available in the area.
You'll find a variety of natural features and landmarks. Wingerworth is known for its series of lakes, including Island Pond, Wall Pond, and Smithy Pond, which offer scenic waterside trails. The Avenue Washlands Nature Reserve, bordering Grassmoor, features reed marsh, ponds, and grasslands. Many routes also traverse reclaimed colliery landscapes, offering unique views of the area's industrial heritage. You might also pass by highlights such as Stubbing Pond Boathouse or Ogston Reservoir.
The routes vary significantly in difficulty. You can find easy, moderate, and challenging options. For instance, routes like Holy Cross Church, Morton – St. Paul's Church loop from Chesterfield are considered easy, while routes such as Beeley Moor Summit – Stubbing Pond Boathouse loop from Wingerworth offer a moderate challenge with significant elevation gain. There are 71 easy, 224 moderate, and 79 difficult routes to choose from.
Yes, the network of trails, including the Five Pits Trail, allows for excellent connectivity to other regional routes and attractions. You can link up with paths leading to places like the Chesterfield Canal and Williamthorpe Ponds Nature Reserve, extending your cycling adventures beyond the immediate area.
Absolutely. A significant draw for cyclists in this region is the transformation of old railway lines and tranquil canal paths into multi-use trails. The Five Pits Trail is a prominent example, offering a mostly surfaced route that follows a former railway line. These types of trails are generally well-suited for road bikes, providing smooth surfaces and gentle gradients.
The area is highly rated by the komoot community, with an average score of 4.6 stars from over 60 reviews. Cyclists often praise the blend of rural tranquility with accessible routes, the well-maintained paths along former railway lines, and the diverse scenery that includes open meadows, woodlands, and reclaimed industrial landscapes.
Yes, many of the road cycling routes in the area are designed as loops, allowing you to start and finish at the same point. For example, the Woodland Stream Trail – Landslip on Commonside Road loop from Wingerworth is a moderate 46.5 km circular route. You can easily filter for circular routes on komoot to find options that suit your preferred distance and difficulty.
Many of the popular cycling routes, especially those utilizing trails like the Five Pits Trail, have designated car parks at various points along their length. Grassmoor Country Park, for instance, located at the northern end of the Five Pits Trail, provides parking facilities, offering a convenient starting point for exploring the trails.
For those seeking a challenge, there are several routes with significant elevation gain. An example is the Spiral Pedestrian Bridge – Climb to Palterton loop from Temple Normanton, a moderate 44.7 km path that features notable climbs and passes through a mix of rural and reclaimed landscapes. There are 79 difficult routes in the wider region for experienced cyclists.
Yes, public transport can be used to access certain areas. Grassmoor Country Park, a key starting point for many trails including the Five Pits Trail, is generally accessible by public transport, though specific bus routes and schedules should be checked locally for the most up-to-date information.


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