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Road cycling routes
United Kingdom
England
South East England
Hampshire
East Hampshire

Headley

The best road cycling routes around Headley

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.

Best road cycling routes around Headley

  • The most popular road cycling route is Liss Riverside Railway…

Last updated: July 4, 2026

41

riders

#1.

View of Frensham Great Pond – Frensham Great Pond Café loop from Headley

33.1km

01:29

310m

310m

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

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Moderate

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

Moderate
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Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

Easy

Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

Easy

Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

Easy
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MCW73
June 17, 2026, Devil's Punch Bowl Cycle Path

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."

Translated by Google

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Lovely quiet roads for riding away from the traffic

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Good cafe with teas, coffees, cakes and food

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Great little Pub in town but no shop

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Frequently Asked Questions

How many road cycling routes are available around Headley?

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.

What kind of terrain can I expect on road cycling routes in Headley?

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.

Are there road cycling routes suitable for beginners or less experienced cyclists?

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.

Are there challenging road cycling routes with significant elevation gain in Headley?

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.

What natural features can I see along the road cycling routes in Headley?

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.

Are there any historical landmarks or points of interest to explore while cycling?

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.

What do other cyclists say about road cycling in Headley?

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.

Are there any circular road cycling routes in Headley?

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.

Can I find scenic viewpoints on the road cycling routes in Headley?

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.

Are there any lakes or ponds accessible along the road cycling routes?

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.

What is the best time of year for road cycling in Headley?

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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