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United Kingdom
England
South East England
Surrey
Tandridge

Caterham-On-The-Hill

The best road cycling routes around Caterham-On-The-Hill

4.6

(407)

9,885

riders

353

rides

Road cycling around Caterham-On-The-Hill offers varied terrain and scenic landscapes within the North Downs and Surrey Hills. The region is characterized by undulating and hilly routes, featuring chalk downlands, ancient woodlands, and open meadows. Cyclists can expect mostly well-paved surfaces, with some challenging climbs and diverse scenery throughout the area. This setting provides a range of road cycling experiences for different fitness levels.

Best road cycling routes around Caterham-On-The-Hill

  • The most popular road cycling route is Box Hill Climb –…

Last updated: July 4, 2026

82

riders

#1.

Box Hill Climb – View from Box Hill loop from Whyteleafe

101km

04:32

950m

950m

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

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Hard

Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

Moderate
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Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult 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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Tips from the Community

Peter
November 27, 2025, Chaldon Church and The Ladder of Salvation Mural

A Saxon church founded in the 10th or 11th Century on the site of an even older church, and altered and added-to over the centuries. On the North wall is the Chaldon Mural, ‘the Ladder of Salvation of the Human Soul’, painted in around 1200 then white-washed over at some point, and revealed again in 1869; a unique work of art and very worth a look.

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A good work out ahead of coffee at either Chiddingstone Castle café or the Tulip.

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Very picturesque village with excellent "Tulip" café right opposite the church

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An absolutely nice and quiet lane, there is much greenery around. The road is a bit narrow, nonetheless the road surface is good for both road and gravel riding. it's mostly flat with little rising, nothing much to bother your legs.

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Michael
August 15, 2025, Outwood Windmill

NIce spot to take on some water

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7 days a week 9-5 I think.

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Nice to ride if quiet but a few 4x4 idiots

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Lovely valley road to ride through. Impressive posh school buildings in nice quiet road.

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Frequently Asked Questions

How many road cycling routes are available around Caterham-On-The-Hill?

There are over 350 road cycling routes in the Caterham-On-The-Hill area, offering a wide range of options for different skill levels. These routes are highly rated by the komoot community, with an average score of 4.6 stars.

What kind of terrain can I expect when road cycling near Caterham-On-The-Hill?

The terrain around Caterham-On-The-Hill is characterized by undulating and hilly routes, featuring chalk downlands, ancient woodlands, and open meadows. You'll find mostly well-paved surfaces, but the area is known for its challenging ascents, including famous climbs like Box Hill and Col du Skelly.

Are there any challenging road cycling routes in the area?

Yes, Caterham-On-The-Hill is well-known for its challenging climbs. A notable difficult route is the Box Hill Climb – View from Box Hill loop from Whyteleafe, which includes the iconic Box Hill ascent. The area also features the challenging Col du Skelly (Beddlestead Lane climb), known for its inconsistency and length.

Are there any easier or moderate road cycling routes suitable for beginners?

While the region is known for its hills, there are plenty of moderate routes. For example, the Chaldon Church – Church Lane, Chaldon loop from Caterham offers a moderate road ride through the countryside. Another good option is the Furnace Lane – Country Lane Near Mark Beech loop from Caterham, which provides varied scenery on a moderate trail.

What scenic spots or landmarks can I see along the road cycling routes?

Road cycling routes often pass through the beautiful Surrey Hills and offer views of the North Downs. You can encounter landmarks such as the Col du Skelly Monument, dedicated to a cyclist. Other scenic spots include Farthing Downs Scenic Road and various viewpoints like View of the High Weald from Gravelly Hill.

Is Caterham-On-The-Hill a good destination for family-friendly road cycling?

The area offers a mix of terrain. While many routes feature challenging climbs, there are also moderate options that families with older children or those seeking a less strenuous ride might enjoy. It's best to check the difficulty ratings and elevation profiles of individual routes on komoot to find the most suitable ones for your family.

What is the best time of year for road cycling in Caterham-On-The-Hill?

The spring and autumn months generally offer pleasant temperatures and beautiful scenery for road cycling in Caterham-On-The-Hill. Summer can also be excellent, though some climbs might be more strenuous in warmer weather. Winter cycling is possible, but be prepared for potentially wet and colder conditions on the exposed downlands.

Are there cafes or pubs along the cycling routes for a stop?

The region around Caterham-On-The-Hill, being popular with cyclists, has various villages and towns along its routes where you can find cafes, pubs, and other amenities for a refreshment stop. Many local establishments are accustomed to catering to cyclists.

Where can I find parking for road cycling routes in Caterham-On-The-Hill?

Parking is generally available in and around Caterham-On-The-Hill, particularly in town centers or designated car parks. For specific routes, it's advisable to check the starting points on komoot, as many routes begin near public parking facilities.

Can I reach Caterham-On-The-Hill by public transport for cycling?

Caterham-On-The-Hill is accessible by public transport, including train services, which can be convenient for cyclists looking to start their rides from the town. Check local train operator policies regarding bikes during peak hours.

What do other road cyclists enjoy most about cycling in Caterham-On-The-Hill?

The area is highly rated by the komoot community, with an average score of 4.6 stars from over 380 reviews. Reviewers often praise the varied terrain, the stunning views across the North Downs and Surrey Hills, and the challenge of iconic climbs like Box Hill and Col du Skelly. The mix of ancient woodlands and open meadows also contributes to a highly enjoyable cycling experience.

Are there any circular road cycling routes around Caterham-On-The-Hill?

Yes, many of the road cycling routes around Caterham-On-The-Hill are designed as loops, allowing you to start and finish in the same location. Examples include the Col du Skelly Monument – View of Kent Downs Vineyards loop from Caterham and the Outwood Windmill – Gayhouse Lane Windmill loop from Whyteleafe South.

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