4.6
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22,663
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Urban hiking trails around Winterfold Wood offer a blend of natural and urban exploration. Winterfold Wood itself is characterized by dense forests of beech and oak, interspersed with open heathland and ancient trees. The area features moderate gradients, with prominent hills like Pitch Hill and Reynards Hill providing elevated viewpoints. While Winterfold Wood is a natural landscape, the surrounding region, including nearby towns, provides numerous urban hiking opportunities.
Last updated: May 1, 2026
9
hikers
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
10
hikers
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

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13
hikers
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
9
hikers
6.18km
01:37
50m
40m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
6
hikers
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
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Nice quick shortcut into town. Some big steps though
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The listed 19th century mill is now used as offices. The building is not open to the public but is clearly visible from Woking Street. Today, Surrey's largest daily newspaper, the "Surrey Advertiser", has its headquarters here.
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Delightful narrow path through a small forest, always directly along the shore. It is accordingly muddy, we recommend hiking boots/wellies!
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Part of the huge Stoke Park grounds, the garden is a favourite spot! With several ponds, a children's paddling pool, an ice cream parlour, bridges and generally wonderful plants, it is sure to delight the hearts of all! The garden is closed (fenced) after sunset
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look out for the famous clock, The Guildford Guildhall Historic Clock, which projects over the High Street from the Guildhall, and which has regularly appeared on television.
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These concrete obstacles were constructed from 1941 during the Second World War and were intended impede the movement of invading German tanks and other armoured vehicles. They constitute perhaps the best surviving example of dragon’s teeth emplacement in Surrey. They are so well preserved that some people even wonder if they are post-war imitations created for TV or a film programme! These defences descend the slope through Thorneycroft Wood to the edge of a channel of the River Wey. They comprise five rows of dragon’s teeth which take the form of flat-topped pyramids made of reinforced concrete. Some of these pyramids are capped by jagged bits of metal that would have supported wire tangles to obstruct passage between and over the dragon’s teeth. Nearby there are also at least three rifle pits formed with cement-filled sandbags.
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This wonderful Jacobean building was founded in 1619 by George Abbot who was Archbishop of Canterbury. Abbot’s Hospital is an almshouse situated at the top of Guildford High Street opposite Holy Trinity Church where George Abbot is buried. The building has become a landmark throughout the centuries and is well worth a visit! Abbot’s Hospital was George Abbot’s gift to the place of his birth. For over 400 years it has provided homes to local residents aged over 60 who are of modest means and of good character. At the time of writing there is accommodation for 27 residents. When the front doors are open passersby can view the fine courtyard inside. There are also regular tours of the ‘Hospital’ to learn about its fascinating history, fine architecture and well-kept grounds (please see https://www.abbotshospital.org/visits-tours/ for timings).
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The acclaimed view looking down Guildford’s sloping High Street typifies the city’s rich historical and natural heritage. This iconic sight is only 200 m from Guildford Castle and is well worth seeing during a nearby hiking, cycling or running tour. The ‘view’ encompasses historic buildings, a pedestrianised street of granite setts that slopes down to the Town Bridge over the River Wey, and the green and steep Mount hill on the North Downs which the historic Pilgrims Way drovers’ road between Guildford and Winchester used to wind its way over. The historic buildings on Guildford’s sloping High Street include the Guildhall constructed about 1550, the Guildhall clock and balcony that overhang the street and date from 1683, the Abbot’s Hospital founded in 1619 and still in use today, and the Angel Gate and Livery Stables building part of which dates from the 1300s. Should you have time, you may wish to also see some of the historic side alleys that join the High Street.
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There are over 20 urban hiking trails in the Winterfold Wood area, catering to various preferences. Most of these, around 20, are rated as easy, with a few moderate options for those seeking a bit more challenge.
The urban hikes around Winterfold Wood vary in length. For example, you can find shorter routes like the Guildford Castle – View of Guildford High Street loop from Guildford, which is about 2.6 km. Longer options include the View of Guildford High Street – Guildford Castle Grounds loop from Guildford, stretching approximately 8.7 km. Durations range from under an hour to a few hours, depending on the trail and your pace.
Yes, many urban hikes around Winterfold Wood are ideal for beginners and casual walkers. For instance, the Guildford High Street – View of Guildford High Street loop from Guildford is an easy 4.4 km route. Another accessible option is the Abbot's Hospital – View of Guildford High Street loop from Guildford, which is about 4.5 km and also rated easy.
The urban trails often pass by significant points of interest. You can explore historical sites like the Peaslake Village, or enjoy natural features such as the unique Perspectives by Giles Miller – Surrey Hills sculpture. Many routes also offer stunning views from spots like View from Pitch Hill and Reynards Hill Viewpoint, providing panoramic vistas across the weald.
Many of the urban trails are suitable for families, especially the numerous easy-rated routes. These paths offer a great way to introduce children to hiking in a manageable urban setting, often with interesting sights along the way. The varied landscape, from dense forests to open heathland, provides an engaging environment for all ages.
Yes, the trails in and around Winterfold Wood are generally dog-friendly. The diverse environment of wooded paths and open heathland provides plenty of opportunities for dogs to enjoy the outdoors. Always remember to keep your dog under control and clean up after them to ensure a pleasant experience for everyone.
Winterfold Wood offers a beautiful hiking experience year-round. Spring brings blooming wildflowers, while autumn showcases vibrant foliage. The moderate gradients make it enjoyable even in cooler months. Elevated spots like Pitch Hill and Reynards Hill are particularly stunning during sunrise or sunset, offering warm hues across the landscape.
Yes, many of the urban hiking routes around Winterfold Wood are circular, making for convenient and enjoyable outings. For example, the Guildford High Street – Abbot's Hospital loop from Guildford is a great circular option, allowing you to start and end at the same point without retracing your steps.
While specific parking details for each urban route may vary, Winterfold Wood itself has designated parking areas. For urban trails starting directly from towns like Guildford, public car parks are available. It's advisable to check local parking information for your chosen starting point.
The area is highly rated by the komoot community, with an average score of 4.67 stars. Reviewers often praise the diverse landscapes, from dense forests to open heathland, and the panoramic views from elevated points like Pitch Hill. The well-maintained trails and the blend of natural beauty with accessible urban elements are frequently highlighted.
Yes, you'll find options for refreshments near many of the urban hiking routes. Peaslake Village, for example, is a popular spot with cafes. The wider region also offers traditional pubs like the Hurtwood Inn in Peaslake, the Red Lion pub in Shamley Green, and the Three Horseshoes pub in Cranleigh, perfect for a post-hike meal or drink.


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