4.5
(110)
5,339
riders
25
rides
Road cycling routes around Old Bolsover traverse a landscape characterized by rolling hills and an escarpment position, offering expansive views over the Derbyshire countryside. The area features a mix of quiet roads and repurposed former railway lines, providing varied terrain for cyclists. This region borders the Peak District, contributing to its diverse geological features including Carboniferous limestones and Permian Magnesian Limestone. The network of routes includes paths through green spaces and areas with historical significance.
Last updated: July 8, 2026
5.0
(2)
42
riders
69.4km
03:08
460m
460m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
35
riders
43.9km
02:03
470m
470m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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36
riders
53.5km
02:28
430m
430m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
28
riders
43.4km
02:09
500m
500m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
28
riders
45.3km
02:19
500m
500m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
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Great combo of Road and fast paced single track riding. Links into a variety of local routes including over to Sherwood Pines.
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Beautiful park full of woodland trails and a serpentine lake, lots to see and explore with a historical chapel and ornamental bridge, cycle hire available too in the park.
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0
Steep climb
0
0
Quiet back lane with few cars. Nice route towards Clumber entrance.
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0
There are over 25 road cycling routes around Old Bolsover, catering to various skill levels. These routes are highly rated by the komoot community, with an average score of 4.0 stars.
The terrain around Old Bolsover is characterized by rolling hills and its strategic position on an escarpment, offering expansive views. You'll find a mix of quiet roads and repurposed former railway lines, providing varied surfaces. The region borders the Peak District, contributing to its diverse geological features, including Carboniferous limestones and Permian Magnesian Limestone.
Yes, Old Bolsover offers several easy road cycling routes. For instance, the Bolsover Castle – Thorpe Hall Ruins loop from Bolsover is a moderate route that can be enjoyed by many. Additionally, former railway lines like the Stockley Trail and Clowne Greenway provide largely traffic-free and peaceful options, ideal for a more relaxed ride.
For those seeking a challenge, some routes around Old Bolsover feature significant elevation gains. The Bolsover Castle – Climb Past the Masts loop from Bolsover, for example, includes over 500 meters of ascent. The region's rolling hills and proximity to the Peak District provide ample opportunities for more demanding rides.
Many routes offer views of significant historical sites. You can often spot Bolsover Castle, a 17th-century mansion with spectacular panoramic views. Other nearby attractions include the majestic ruins of Sutton Scarsdale Hall and the archaeologically significant Creswell Crags, which features ancient caves like Robin Hood's Cave.
Absolutely. Old Bolsover is situated on an escarpment, providing far-reaching views over the Derbyshire countryside, including the Vale of Scarsdale and towards the Peak District National Park. The Backhills and Surprise View, accessible from the High Street, are known for their spectacular panoramas. Many routes also offer glimpses of Bolsover Castle, which itself provides excellent vantage points.
Yes, many of the road cycling routes around Old Bolsover are designed as loops. For example, the Clumber Park Bridge – Clumber Park loop from Bolsover is a popular circular path leading through parkland. The Pleasley Trails also comprise three interconnected railway paths, forming a circular route.
While specific cafes and pubs directly on every route are not detailed, Old Bolsover is a market town, and the surrounding villages often have local establishments. Many routes pass through or near towns and villages where you can find places to stop for refreshments. The local enthusiasm for cycling, evidenced by the Bolsover and District Cycling Club, suggests a welcoming environment for cyclists.
The diverse landscape of Old Bolsover can be enjoyed throughout much of the year. Spring and autumn offer pleasant temperatures and beautiful scenery, with wildflowers in bloom along trails like the Clowne Greenway in spring. Summer provides longer daylight hours, while winter conditions can vary, with some routes potentially being more challenging due to weather.
Yes, the area offers family-friendly cycling options, particularly on the repurposed former railway lines. Trails like the Stockley Trail and the Clowne Greenway are largely traffic-free and provide a safe, peaceful environment for families to cycle together through natural settings and areas rich in wildlife.
Beyond the rolling hills and escarpment views, you can explore several natural features. The Carr Vale Nature Reserve, accessible via the Stockley Trail, is excellent for birdwatching. The Clowne Greenway winds through cuttings abundant with wildflowers, insects, mammals, and birds. The region's geology, with its varied limestones and gritstones, also contributes to the scenic beauty.
Yes, parking is generally available in and around Old Bolsover, especially near trailheads and in the town center. Many of the former railway line trails, such as those leading to Carr Vale Nature Reserve or the Clowne Greenway, often have designated parking areas nearby to facilitate access for cyclists.


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