4.5
(189)
8,359
riders
13
rides
Road cycling routes around Headley traverse a varied landscape characterized by woodlands, open countryside, and charming village centers. The area features diverse terrain, from gentle paths to routes with significant elevation changes, offering exploration opportunities for different fitness levels. Cyclists can experience both historical sites and natural features like picturesque ponds and heathlands. The region's varied topography provides a range of road cycling experiences.
Last updated: July 4, 2026
41
riders
33.1km
01:29
310m
310m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
13
riders
28.9km
01:25
400m
400m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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11
riders
21.8km
01:05
260m
260m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
6
riders
26.4km
01:17
270m
270m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
8
riders
19.8km
01:05
210m
210m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
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Following the 2011 opening of the Hindhead Tunnel, the old A3 through the Devil’s Punch Bowl was closed and dug up. Nature completely reclaimed the tarmac, transforming it into peaceful, scenic paths. Today, cyclists enjoy paved, car-free routes tracing the rim of the dramatic, sandstone amphitheater.
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The old A3 road, which once choked the Devil’s Punch Bowl with traffic, has been transformed into a peaceful, paved walking and cycling trail. Following the 2011 tunnel bypass, nature reclaimed the tarmac, creating a scenic, accessible path that seamlessly connects visitors to the wider Surrey Hills network.
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Erected in 1851 by judge Sir William Erle, the granite Celtic cross on Gibbet Hill was built to dispel local fears of evil spirits. It marks the notorious site where three highwaymen were hanged and displayed in chains in 1787 for the brutal murder of an unknown sailor.
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One way is so fast, other way not so much but great views either way
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The most typical feature in the design of Celtic crosses is the circle connecting the horizontal and vertical bars. This is sometimes interpreted as a symbol of the sun; in this sense, Celtic crosses are sometimes also called sun crosses. I found the following meditative reflection on this topic while working as a chaplain in the Protestant deanery of Nassauer Land: "The sun cross is a special symbol of Celtic Christianity. It can become a symbol of spirituality. + What you can practice – the horizontal arm of the cross. Your conscious rituals, prayers, quiet moments. The attention you give to the sacred. + What happens to you – the vertical arm of the cross. Experiences that touch and transform you. Moments in which you sense something greater than yourself. + What gives you interpretation – the circle that encloses both. Words, stories, and traditions that help you understand and share these experiences. Spirituality connects you to sources of strength that reach deeper than what you can see. For me as a Christian, spirituality is a word for encountering the God who revealed himself in Jesus."
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Lovely quiet roads for riding away from the traffic
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Headley offers a wide selection of road cycling routes, with over 600 tours available. This includes a diverse range of options suitable for various fitness levels and preferences.
Road cycling routes around Headley feature a varied landscape, including woodlands, open countryside, and charming village centers. The terrain can range from mostly well-paved, gentle paths to more challenging routes with significant elevation changes, sometimes incorporating unpaved segments.
Yes, Headley has plenty of options for beginners. Approximately 148 of the available road cycling routes are rated as easy. An example of an easy route is the Liss Riverside Railway Path – Liss Village Centre loop from Bordon, which is 17.6 miles long.
For those seeking a challenge, Headley offers routes with notable elevation gains. Some longer routes can feature up to 3,000 feet of ascent. There are 38 routes rated as difficult, and 417 as moderate, providing ample opportunities for more experienced cyclists. The View of Frensham Great Pond – Mill Bridge Over the River loop from Bordon is a moderate route with over 370 meters of elevation gain.
Cyclists can enjoy a variety of natural features. The region is home to picturesque lakes like Frensham Little Pond, surrounded by pine trees and sandy hills. You might also encounter the unique landscapes of Headley Heath, with its diverse flora, or the ancient woodlands of Nower Wood. Hollywater Meadows, with its restored hedgerows and grassland, also offers scenic views.
Yes, Headley's routes often pass by historical sites. You could encounter the Celtic Cross on Gibbet Hill, a monument offering excellent views, or cycle through the historic Liss Village Centre, which provides pubs, cafes, and shops. While not directly on all routes, the area is rich in history, with sites like Farnham Castle Keep nearby.
The komoot community highly rates road cycling in Headley, with an average score of 4.5 stars from over 180 reviews. Cyclists often praise the varied terrain, from quiet woodlands to open countryside, and the well-maintained paths that cater to different ability levels. Over 8,000 road cyclists have used komoot to explore the area.
Many of the road cycling routes in Headley are designed as loops, allowing you to start and finish at the same point. For example, the Mill Bridge Over the River – Frensham Church loop from Headley is a popular circular route that takes you through scenic landscapes and past historical points of interest.
Absolutely. The diverse landscape of Headley offers several opportunities for scenic views. You can find viewpoints such as the Devil's Punch Bowl Picnic Site or enjoy vistas from Gibbet Hill. Routes often traverse areas with open countryside, providing expansive views of the surrounding natural beauty.
Yes, the region features several beautiful lakes and ponds. Frensham Little Pond is a notable example, offering picturesque scenery. Other bodies of water like Stockbridge Pond and Folly Pond are also part of the natural landscape, providing tranquil spots along or near cycling paths.
Headley's varied landscape makes it suitable for road cycling across multiple seasons. Spring and autumn offer pleasant temperatures and beautiful scenery, with woodlands showcasing vibrant colors. Summer provides longer daylight hours, while milder winter days can still be enjoyable, though some routes might be affected by weather conditions.


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