4.7
(56)
3,443
riders
240
rides
Road cycling routes around Chesterfield offer diverse terrain, benefiting from the region's proximity to the Peak District. The landscape features rolling hills, converted railway lines, and canal towpaths, providing varied cycling experiences. Riders can explore woodlands and open farmland, with routes often traversing through scenic countryside. The area's geography allows for both gentle rides along waterways and more challenging climbs into the surrounding hills.
Last updated: April 24, 2026
4.8
(4)
49
riders
58.8km
03:05
930m
930m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.
4
riders
77.1km
04:45
1,250m
1,250m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.

Sign up for free
4.6
(7)
130
riders
49.3km
02:38
640m
640m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
4.3
(3)
89
riders
36.2km
01:53
520m
520m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
5.0
(4)
84
riders
46.1km
02:19
510m
510m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
5.0
(1)
74
riders
47.5km
02:26
730m
730m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
5.0
(2)
69
riders
36.0km
01:55
430m
430m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
70
riders
76.5km
03:54
780m
780m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
5.0
(2)
68
riders
29.7km
01:32
340m
340m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
4.0
(2)
55
riders
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
Get access to more routes and recommendations from other explorers.
Sign up for free
Already have an account?
Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.
Start today with a free account
Your next adventure awaits.
Login or Signup
Popular around Chesterfield
Nice cafe with good coffee and nice Bakewell tart great after finishing a hike
0
0
a nice climb and generally traffic free as it's closed forever
0
0
Went for a Bakewell tart but also tried the Bakewell pudding, it was amazing. It's a great shop.
0
0
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.
0
0
There are over 240 road cycling routes around Chesterfield, offering a wide variety of experiences. These include options for different skill levels, from moderate rides to more challenging climbs.
Road cycling around Chesterfield features diverse terrain, including rolling hills, converted railway lines, and picturesque canal towpaths. The region's proximity to the Peak District means you can expect varied landscapes, from tranquil woodlands and open farmland to more demanding ascents into the hills.
Yes, while many routes involve rolling hills, the area also benefits from converted railway lines and canal towpaths which often provide flatter, traffic-free sections. These can be ideal for beginners or families looking for a more relaxed ride. For example, the Chesterfield Canal Towpath offers a picturesque and generally gentle cycling experience.
The spring and summer months generally offer the most pleasant conditions for road cycling around Chesterfield, with milder weather and longer daylight hours. Autumn can also be beautiful with changing foliage. While some routes are accessible year-round, winter rides may require more caution due to potentially colder temperatures and wet conditions.
Many routes pass by significant landmarks and natural features. You might encounter historic sites like Chatsworth House or Hardwick Hall, or enjoy the scenic beauty of the Peak District. Specific highlights include the Brick Sphere Sculpture at Holmebrook Valley Park, Walton Dam, and the Poolsbrook Country Park Lake. The Trans Pennine Trail: Brimington to Staveley Section also offers a glimpse into the region's industrial heritage.
The road cycling routes in Chesterfield are highly rated by the komoot community, with an average score of 4.6 stars from over 50 reviews. Cyclists frequently praise the diverse landscapes, from challenging climbs in the Peak District to scenic rides along converted railway lines and canal towpaths, and the opportunity to explore historic estates.
Yes, Chesterfield and the surrounding Derbyshire area are known for their converted railway lines and canal towpaths, which offer excellent traffic-free cycling opportunities. The Chesterfield Canal Towpath and sections of the Trans Pennine Trail are good examples, providing peaceful rides through the countryside.
Absolutely. Many of the popular road cycling routes around Chesterfield are designed as loops, allowing you to start and finish in the same location. Examples include the Ladybower & Stanage Edge loop and the Beeley Moor Summit – Cutthorpe Curves loop from Chesterfield.
For those seeking a challenge, routes like the Chatsworth House & Hardwick Hall loop from Chesterfield, at 47.9 miles with significant elevation, or the Thornhill Lane – Winnats Pass loop from Chesterfield, which is 80.2 miles and features over 1100 meters of climbing, offer demanding rides through the Peak District.
Many road cycling routes in the Chesterfield area pass through or near villages and towns where you can find cafes, pubs, and other amenities for refreshments. Routes that visit popular attractions like Chatsworth House also offer facilities. Planning your route in advance can help identify suitable stop-off points.
Many routes start from Chesterfield town center or surrounding villages, where public parking is generally available. For routes venturing further into the Peak District, specific trailheads or village car parks can serve as starting points. Always check local parking regulations and availability before your ride.


Check out more Road cycling routes throughout Chesterfield below and find the perfect route in your destination.
Browse the best Road cycling routes in other regions.