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United Kingdom
England
South East England
Buckinghamshire
Chiltern

Cholesbury-Cum-St Leonards

The best walks and hikes around Cholesbury-Cum-St Leonards

4.6

(3280)

20,703

hikers

24

hikes

Hikes around Cholesbury-Cum-St Leonards explore the rolling hills and ancient woodlands of the Chiltern Hills Area of Outstanding Natural Beauty. The landscape is characterized by extensive beech forests, open meadows, and chalk grasslands. Many trails incorporate historical sites, including the well-preserved Iron Age earthworks of Cholesbury Camp.

Best hiking trails around Cholesbury-Cum-St Leonards

  • The most popular hiking route is Cholesbury Camp and St Leonard's Church loop from Hawridge Common β€” Chiltern Hills, a 4.5 mile (7.3 km) trail that takes about 1 hour 55 minutes to complete. This easy route features a walk around the historic Cholesbury Iron Age Fort.
  • Another top favourite among local hiking enthusiasts is Cholesbury and Hawridge loop – Chiltern Hills, a moderate 5.1 mile (8.2 km) path. The terrain consists of a mix of woodland tracks and open field paths typical of the Chilterns.
  • Local hiking enthusiasts also love the Hawridge, Ramscoat Wood and Asheridge – Chiltern Hills, a 5.9 mile (9.5 km) trail leading through Ramscoat Wood, often completed in about 2 hours 30 minutes.
  • Hiking around Cholesbury-Cum-St Leonards is defined by its ancient beech woodlands, rolling chalk hills, and historic earthworks. The network of footpaths provides routes suitable for a range of fitness levels.
  • The routes in Cholesbury-Cum-St Leonards are highly rated by the komoot community with an average score of 4.6 stars from over 1,000 reviews. More than 9,000 hikers have used komoot to explore Cholesbury-Cum-St Leonards's varied terrain.

Last updated: May 3, 2026

5.0

(2)

22

hikers

#1.

Cholesbury Camp and St Leonard's Church loop from Hawridge Common β€” Chiltern Hills

7.33km

01:56

70m

70m

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

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Easy

Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

Moderate
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Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

Moderate

Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

Moderate

Hard hike. Very good fitness required. Mostly accessible paths. Sure-footedness required.

Hard
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Popular around Cholesbury-Cum-St Leonards

Unforgettable trails – serene wilderness in the Chiltern Hills

Road Cycling Routes around Cholesbury-Cum-St Leonards

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Gravel biking around Cholesbury-Cum-St Leonards

Running Trails around Cholesbury-Cum-St Leonards

Cycling around Cholesbury-Cum-St Leonards

Other adventures around Cholesbury-Cum-St Leonards

Unforgettable trails – serene wilderness in the Chiltern Hills

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Nature Kicks

Tips from the Community

Gemsquashed
April 13, 2024, Full Moon Pub

They advertised on Sunday's that they don't just do roast dinners but also sandwiches, perfect for a pre or post hike lunch. Excellent garden when it's warm and a covered terrace when it's cold. Good to book!

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St Mary's Church was first mentioned in 1227. In the 19th century, it fell into disrepair, and was subsequently rebuilt in 1856 by the architect William White. He used flint-and-brick materials and gave the church a style specific to the 1850s known as "constructional polychromy" (the practice of architectural decoration using a variety of colours). The tower, I find, is particularly attractive. Worth stopping at: it's a lovely little church.

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The history of the village of St Leonard's is tightly connected with the chapel of Leonard's - and this dates back to the 12th century. The present church, however, was built in the 15th century. As many such places, it has had a tumultuous history. For instance, after the Dissolution of the Monasteries, the chapel continued being used and Queen Elizabeth inquired in 1586 into why the chapel and the lands had not reverted to the Crown. The church feel into disrepair in the 17th century. What can be seen today is in the simple Queen Anne style, and was rebuilt around 1700s. The whitewashed walls are striking and give the church a unique look. In the winter, it can look brilliant after snow, and in the spring, when the snowdrops come up (plenty of them in the church grounds), it also looks terrific.

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This green walk begins in one forest and ends in another, with gorgeous green views throughout of the valley of the dry valley of Asheridge Bottom. The sweeping valley view should take your breath away.

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This is a nice and long path and track between Cholesbury and Chesham. A beautifully varied one, too: woodlands, views of rolling hills and fields, meadows, cattle... essentially, everything good that the British countryside has to offer!

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This is an impressive structure (although it's not easy to get up close to it), an imposing sight over the street. It's disused windmill. The first windmill here was built in the 17th century, but later a smock mill was constructed in 1863 by the Norwich Wind and Steam Company. Eventually, the building was converted into a private residence in the early 20th century. It's a Grade II listed building.

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This is a classic country pub in an achingly pretty village. There's a lovely beer garden and delicious food in the restaurant. The pub is just a short walk from the Chiltern Heritage Trail and makes for an excellent pitstop or objective on a walk in the hills here.

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I wish I lived in a windmill! What a fantastic structure. It might be a house or a studio, I can't really tell from the roadside.

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Frequently Asked Questions

Are the hiking trails around Cholesbury-Cum-St Leonards suitable for families with children?

Yes, the area is well-suited for family walks. The landscape features many gentle paths through woodlands and across open commons, which are perfect for shorter legs. You'll find a dozen easy-rated trails, typically on well-trodden paths with minimal elevation changes, making for a relaxed day out.

Can I take my dog on the trails?

Absolutely. The extensive network of footpaths through the Chilterns' woodlands and fields is great for dog walking. However, please be mindful of local wildlife and any livestock in the fields. It's best to keep your dog on a lead, especially in nature reserves or areas with ground-nesting birds.

What is the terrain like on a typical hike in this area?

Most hikes feature a pleasant mix of terrain characteristic of the Chiltern Hills. Expect to walk on shaded woodland tracks under magnificent beech trees, cross open chalk grasslands with wide-ranging views, and follow paths along quiet country lanes. The hills are rolling rather than steep, offering gentle climbs.

Are there any circular walks available?

Yes, the vast majority of the walking routes in this area are circular. They are designed to bring you back to your starting point, which is often a village, a common, or a local pub. This makes planning your hike straightforward, especially if you are arriving by car.

What historical points of interest can I see on a walk?

The most significant historical site is Cholesbury Camp, a large and well-preserved Iron Age hillfort. Many walks incorporate its impressive earthwork ramparts. You can also find St. Lawrence's Church uniquely situated inside the fort. Some longer routes may also pass sections of Grim's Ditch, another ancient earthwork.

Are there any good pub walks in the area?

Many trails conveniently start and end near traditional country pubs. For a rewarding walk, you could try the Cholesbury Windmill and Asheridge Bottom loop from Cholesbury β€” Chiltern Hills. It begins in the village, making it easy to enjoy refreshments at a local pub like The Full Moon after your hike.

How do I get to the trails by public transport?

Getting to the area by public transport can be challenging as the villages are quite rural. The nearest train stations are in Tring or Wendover, both several miles away. From there, you would likely need to take a local bus service, which may be infrequent, or a taxi to reach the trailheads.

Where is the best place to park for a hike?

There is no single large car park for the area. Most hikers find informal on-street parking in villages like Cholesbury or Hawridge, particularly near the commons. Please park considerately, ensuring you do not block residents' access or narrow country lanes. Some local pubs may also allow parking for patrons.

What are the best viewpoints in the Cholesbury area?

For some of the best panoramic views in the Chilterns, head towards Coombe Hill. At 852 feet, it's the highest viewpoint in the region, offering stunning vistas over the Aylesbury Vale. Nearby Pitstone Hill is another excellent spot, known for its pristine chalk grassland and far-reaching views.

Are there any long-distance trails that pass through the area?

Yes, a section of The Ridgeway National Trail, an ancient path that's been used for over 5,000 years, runs near the parish. You can easily join parts of this famous trail on some of the longer local loops, such as the St Mary's Church and Pavis Wood loop from Cholesbury β€” Chiltern Hills, which connects with it.

What do other hikers enjoy most about Cholesbury-Cum-St Leonards?

The area is highly rated by the komoot community. Reviewers often praise the beautiful ancient beech woodlands, the peace and quiet of the trails, and the fascinating history of Cholesbury Camp. The mix of shaded woods and open hillsides is frequently mentioned as a highlight.

How many hiking trails are there to choose from?

You can explore over 20 hiking routes around Cholesbury-Cum-St Leonards. The collection includes about a dozen easy walks perfect for a casual stroll, 11 moderate routes for a more substantial hike, and one difficult trail for those seeking a full-day challenge.

Most popular routes around Cholesbury-Cum-St Leonards

Family-friendly hikes around Cholesbury-Cum-St Leonards

Most popular attractions around Cholesbury-Cum-St Leonards

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