4.6
(405)
15,022
riders
357
rides
Road cycling routes around Headley traverse a diverse landscape, characterized by open heathland, chalk downland slopes, and mixed woodland, notably within the Surrey Hills National Landscape. The region features well-paved surfaces, with some routes incorporating unpaved segments that add variety to the terrain. Cyclists can expect a mix of flat sections and rolling hills, with elevation gains ranging from moderate to significant. The area's natural features, including Headley Heath and the River Wey, provide scenic backdrops for road cycling.
Last updated: July 4, 2026
4.0
(3)
307
riders
93.3km
05:02
1,630m
1,630m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.
5.0
(4)
359
riders
41.6km
01:55
490m
490m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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4.9
(9)
199
riders
39.6km
01:49
410m
410m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
5.0
(3)
124
riders
12.7km
00:37
180m
180m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
4.5
(4)
138
riders
40.0km
01:46
290m
290m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
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Stunning and typical countryside road and scenery.
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0
So pretty, very quiet but the Road Surface is awful
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0
Boar Hill on Coldharbour Lane is a tough little climb with a kick at the end. You climb from 289 feet (88 m) in Dorking up to about 656 feet (200 m) near Robbing Gate. The area is popular with bikes and this climb is easily linked with Box Hill.
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There are over 360 road cycling routes available around Headley, catering to various skill levels. You'll find a wide selection, from easy rides to more challenging excursions.
The terrain around Headley is quite diverse, featuring open heathland, chalk downland slopes, and mixed woodland, particularly within the Surrey Hills National Landscape. Most routes have well-paved surfaces, but some may include unpaved segments, adding variety to your ride. You can expect a mix of flat sections and rolling hills.
Elevation gains on Headley's road cycling routes vary significantly. Easy routes, like the Box Hill Climb – View from Box Hill loop from Headley, might have around 180 meters (600 feet) of ascent. More challenging routes, such as the View from Box Hill – Box Hill Climb loop from Leatherhead, can feature over 1,600 meters (5,200 feet) of climbing, offering a good workout for experienced cyclists.
Yes, Headley offers over 70 easy road cycling routes. These typically feature gentle gradients and shorter distances, making them ideal for beginners or those looking for a relaxed ride. An example is the Box Hill Climb – View from Box Hill loop from Headley, which is 12.7 km long and takes about 37 minutes.
Absolutely. Headley has over 50 difficult road cycling routes designed for experienced riders. These routes often include significant elevation gains and longer distances. The View from Box Hill – Box Hill Climb loop from Leatherhead is a prime example, covering 93.4 km with over 1,600 meters of ascent.
Many routes pass through or near notable natural features. You can explore areas like Headley Heath, known for its open heathland and mixed woodland. The River Wey, with historic sites like Headley Mill, is also a prominent feature. Cyclists often encounter highlights such as the Box Hill Climb, River Mole Stepping Stones, or the Sheepleas Nature Reserve.
Yes, Headley's routes offer several scenic viewpoints. The Salomons Memorial Viewpoint and View from Colley Hill are popular spots that provide expansive views of the surrounding landscape, including the Surrey Hills.
The road cycling routes around Headley are highly rated by the komoot community, with an average score of 4.6 stars from over 360 reviews. More than 15,000 road cyclists have used komoot to explore the area, often praising the varied terrain and beautiful natural backdrops.
Many of the road cycling routes around Headley are designed as loops, allowing you to start and finish at the same point. Examples include the View from Box Hill – Destination Bike Box Hill loop from Tadworth and the View from Box Hill – Destination Bike Box Hill loop from Brockham, which offer convenient circular options.
While specific cafes and pubs aren't listed for every route, the villages and hamlets around Headley, such as Standford, often provide opportunities for refreshment stops. Many routes are designed to pass through or near these areas, making it easy to find a place for a break.
Headley offers good cycling conditions for much of the year. Spring and summer provide pleasant weather for exploring the heathlands and woodlands. Autumn is particularly scenic with vibrant foliage, especially around areas like Ludshott Common. Winter cycling is also possible, though some unpaved segments might be more challenging in wet conditions.
Yes, Headley has a good selection of easy routes that are suitable for families. These routes typically have gentler gradients and are shorter in duration, allowing for a more relaxed pace. The diverse landscapes, including Headley Heath, provide a pleasant environment for family outings.


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