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Road cycling routes
United Kingdom
England
East Midlands
Derbyshire

Chesterfield

The best road cycling routes around Chesterfield

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.

Best road cycling routes around Chesterfield

  • The most popular road cycling route is Ladybower & Stanage…

Last updated: April 24, 2026

4.8

(4)

49

riders

#1.

Ladybower & Stanage Edge loop

58.8km

03:05

930m

930m

Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.

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Hard

Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.

Hard
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Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate
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Popular around Chesterfield

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Spectacular rides in Central England – e-bike trials by Halfords

Cycling around Chesterfield

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Spectacular rides in Central England – e-bike trials by Halfords

Cycling Collection by

Halfords UK

Tips from the Community

Chris Shannon
April 26, 2026, Beeley Moor

Great views and is normally quite so worth a visit

0

0

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

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0

Went for a Bakewell tart but also tried the Bakewell pudding, it was amazing. It's a great shop.

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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

Great views of the Edge

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0

Nice lanes, quiet traffic

0

0

Thomas
May 6, 2025, Beeley Moor

Great views but exposed to weather

0

0

Frequently Asked Questions

How many road cycling routes are available around Chesterfield?

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.

What is the typical terrain like for road cycling in the Chesterfield area?

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.

Are there road cycling routes suitable for beginners or families in Chesterfield?

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.

What is the best time of year for road cycling around Chesterfield?

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.

What interesting landmarks or sights can I see along the road cycling routes?

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.

What do other road cyclists enjoy most about the routes in Chesterfield?

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.

Are there any traffic-free options for road cyclists in the Chesterfield area?

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.

Can I find circular road cycling routes starting from Chesterfield?

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.

What are some of the longer and more challenging road cycling routes available?

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.

Are there places to stop for refreshments along the cycling routes?

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.

Where can I find parking for road cycling routes in Chesterfield?

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.

Most popular routes around Chesterfield

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