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Great And Little Hampden

The best road cycling routes around Great And Little Hampden

4.5

(154)

8,394

riders

376

rides

Road cycling routes around Great And Little Hampden traverse the undulating Chiltern Hills Area of Outstanding Natural Beauty. The terrain features steady inclines and descents, providing a varied cycling experience. Cyclists encounter picturesque beech woodlands and open vistas, particularly from elevated points like Coombe Hill, which offers views across the Aylesbury Vale. The region's geology contributes to its rolling landscape, making it suitable for road cycling.

Best road cycling routes around Great And Little Hampden

  • The most popular road cycling…

Last updated: May 16, 2026

4.0

(1)

44

riders

#1.

Bledlow Ridge – Lacey Green Windmill loop from Chilterns National Landscape

36.6km

01:52

400m

400m

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

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

Moderate

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

Easy
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Tips from the Community

AliG
October 5, 2025, Wendover Village Centre

Stop at No2 Pound Street (adjacent to the mini roundabout up the hill) Their main business is a delicatessen specialising in cheese and wine ... but you can grab a tea/cofffee with cake or a toastie, Sit outside or in depending on the weather! Highly recommended. If you've room in your saddlebag, grab a bottle of wine, with some excellent cheese, having taken note of the expert advice from the staff!

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Lovely quite country road with amazing views - was initially concerned that it was very narrow but only encountered one car in the whole segment on a weekday afternoon - well worth seeking out

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Eamon Mc
April 20, 2025, Pednor House

A step/ride back to the 17th century!

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In the summer there are tours for Β£3 donation from 2pm on Sunday

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Lovely little town, had a roast dinner here in a Japanese restaurant of all things!

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foxy44
August 20, 2024, Pednor House

Pednor House is a Grade II listed building in Chartridge, Buckinghamshire. Originally a 17th-century farmhouse, it was enlarged in 1910 under the architects Forbes and Tate in the Arts and Crafts style. The house is a large U-shaped structure with a cylindrical dovecote and stands in a beautiful setting. The grounds were originally designed by Gertrude Jekyll.

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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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The War Memorial was put here in 1920. The inscription 'PRO PATRIA' means 'for one's country'. Look to the opposite side of Windsor Lane - 11 trees were planted here, one for each of the fallen. (Keep in mind that more names were added after World War 2.)

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Frequently Asked Questions

How many road cycling routes are available around Great And Little Hampden?

There are over 370 road cycling routes available around Great And Little Hampden, offering a wide range of options for different skill levels and preferences. The komoot community has rated these routes highly, with an average score of 4.5 stars.

What kind of terrain can I expect on road cycling routes in Great And Little Hampden?

The terrain around Great And Little Hampden is characterized by the undulating hills of the Chilterns, providing a varied and engaging cycling experience. You can expect both steady inclines and descents, with routes frequently passing through picturesque beech woodlands and open vistas. The general rolling landscape offers a continuous challenge for cyclists.

What natural features and viewpoints can I see while road cycling around Great And Little Hampden?

Road cyclists can enjoy stunning views, particularly from elevated points like Coombe Hill Viewpoint and Boer War Memorial, which offers far-reaching vistas across the Aylesbury Vale. The routes often pass through picturesque beech woodlands, and in spring, areas adorned with bluebells. Keep an eye out for Red Kites, a bird of prey common in the region, soaring overhead.

Are there any notable landmarks along the road cycling routes?

Yes, several notable landmarks can be incorporated into your rides. Besides the prominent Coombe Hill Viewpoint and Boer War Memorial, you might encounter the distinctive chalk hill carving of Whiteleaf Cross near Princes Risborough, known for its challenging climb. Many routes also pass through charming villages characteristic of the Chilterns.

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

Yes, there are routes suitable for beginners. For example, the Penfold Lane – Temperance Hall, Chesham loop from Prestwood is an easy 31.6 km route with moderate elevation gain, offering a good introduction to the area's cycling. There are 143 easy routes in total, providing gentler options.

Where can I find more challenging road cycling routes in the area?

For more challenging rides, the Chilterns offer significant climbs. Coombe Hill features a 3.2 km climb via Coombe Road with an average gradient of 5.2%. The 'Whiteleaf Climb' from Monks Risborough is also known for its increasing steepness. Routes starting from nearby Great Missenden often incorporate tougher climbs like Whiteleaf, Wardrobes Lane, Kingston Hill, and Watlington Hill Road, forming part of what's known as the 'Chiltern 100'. There are 18 difficult routes available for experienced cyclists.

What is the best time of year for road cycling in Great And Little Hampden?

The best time for road cycling in Great And Little Hampden is generally from spring through autumn. Spring offers the beauty of bluebells in the woodlands, while summer provides longer daylight hours. Autumn brings vibrant foliage. While cycling is possible year-round, be prepared for potentially wet or icy conditions in winter, and always check local weather forecasts.

Is parking available for cyclists in Great And Little Hampden?

While specific dedicated cyclist parking isn't detailed, Great And Little Hampden and surrounding villages like Great Missenden offer various public parking options. It's advisable to check local council websites or parking apps for specific car park locations and charges before your visit.

How can I reach Great And Little Hampden by public transport with my bike?

Great And Little Hampden are located within the Chiltern Hills, and nearby towns like Great Missenden have train stations with connections to London Marylebone. You should check the specific train operator's policy regarding bikes, as restrictions often apply during peak hours. Buses also serve the area, but bike carriage is usually limited to folding bikes.

Are there cafes or pubs along the road cycling routes for a break?

Yes, the Chilterns region is dotted with charming villages and market towns that offer cafes and pubs. Many routes will pass through or near these establishments, providing opportunities for refreshments and breaks. Great Missenden, for instance, is a popular starting point and offers several options for cyclists.

Are there family-friendly road cycling routes in the area?

While the Chilterns are known for their undulating terrain, there are quieter roads and less challenging loops that can be suitable for families with older children or those seeking a more relaxed ride. It's recommended to choose routes with lower elevation gain and less traffic, such as some of the 143 easy routes available, and always assess the route's suitability for your family's experience level.

What do other road cyclists enjoy the most about road cycling in Great And Little Hampden?

The area is highly rated by the komoot community, with an average score of 4.5 stars from over 130 reviews. Reviewers often praise the picturesque landscapes, the engaging undulating terrain, and the stunning views from elevated points. The variety of routes, from moderate challenges like the The Lee Village Green – Temperance Hall, Chesham loop from Prestwood to easier options, is also frequently highlighted.

Most popular routes around Great And Little Hampden

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