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United Kingdom
England
East Of England
Hertfordshire
Three Rivers
Batchworth

Chilterns Cycleway: Rickmansworth to Princes Risborough Loop

Hard

5.0

(1)

16

riders

Chilterns Cycleway: Rickmansworth to Princes Risborough Loop

05:20

84.3km

730m

Cycling

Embark on the Chilterns Cycleway: Rickmansworth to Princes Risborough Loop for a challenging touring bicycle adventure through the Chilterns National Landscape. This difficult route spans 52.4 miles (84.3 km) and features a significant 2381 feet (726 metres) of elevation gain, taking approximately 5 hours and 19 minutes to complete. You will pedal through quiet woodlands and over rolling chalk hills, enjoying open views and the chance to spot Red Kites, with a notable viewpoint at the John Hampden Monument.

Planning your ride requires good fitness due to the hilly terrain and some unsurfaced sections that can be rutted or muddy, especially after rain. For these conditions, a mountain bike or gravel bike is often more suitable than a road bike. The Chilterns Cycleway is well-signposted, making navigation straightforward, and Princes Risborough offers a convenient railway station if you plan to use public transport.

This loop offers a rewarding experience as you traverse the stunning Chilterns Area of Outstanding Natural Beauty, passing through charming villages and past picturesque spots like The Lee Village Green. The 'lumpy' nature of the route, with its steep climbs, is balanced by the beautiful scenery, including views of Bledlow Valley, making every pedal stroke worthwhile.

Last updated: April 23, 2026

Waypoints

A

Start point

Bus stop

Get Directions
1

3.28 km

Colne Valley Trail

Highlight (Segment) • River

Gravel trail suitable for all bike types. It runs alongside the River Colne and the Grand Union Canal so plenty of nice water views.

Tip by

2

24.1 km

Grove's Windmill, Coleshill

Highlight • Monument

Grove's Windmill, Coleshill, is a tower windmill built in 1856, which ceased operations around 1903.

Tip by

3

38.0 km

Descent at John Hampden Monument

Highlight (Segment) • Viewpoint

Beautiful countryside with a link to John Hampden who died in 1643 in the English Civil War.

Tip by

4

43.5 km

Descent Into Princes Risborough, Chilterns

Highlight (Segment) • Viewpoint

It's a reasonably safe descent into Princes Risborough. If you're coming the other way, it's straight up. The road surface is smooth, so you don't have to slow down for too many potholes but it's not that wide, so you'll have to be mindful of cars going the other way. And that's difficult as the views are incredible. Stunning all the way. You'll spot plenty of Red Kites here, looking to swoop on their prey. There is also a right turn on to a bigger road, so you'll have to kill your speed for that. But then it kicks on down again and you'll reach 70kmh if you're brave enough as the road is wide and straight and you'll see danger with plenty of time. Watch for pheasants stepping out into your way too.

Tip by

5

61.8 km

The Lee Village Green

Highlight • Viewpoint

As English villages in the Chiltern Hills go, this one is one of the most attractive. This is the kind of place I tend to think of when I read Agatha Christie's Miss Marple.

The village name is Anglo-Saxon and means "a woodland clearing". Another little fun fact: Sir Arthur Lasenby Liberty (1843–1917), proprietor of the famous Regent Street (London) store, Liberty & Co., lived here and built a Manor house here in 1900. He was associated with the Art Nouveau style.

Tip by

6

78.3 km

Chorleywood Common Scenic Route

Highlight (Segment) • Trail

A nicer route through Chorleywood that takes you around the common, over the railway track and down a single-track lane. Much better than going straight through the centre.

Tip by

B

84.3 km

End point

Bus stop

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Way Types & Surfaces

Way Types

58.7 km

8.45 km

7.50 km

4.96 km

4.78 km

< 100 m

Surfaces

48.6 km

30.2 km

3.61 km

1.17 km

787 m

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Elevation

Elevation
Nothing selected – click and drag below to see the stats for a specific part of the route.

Highest point (250 m)

Lowest point (40 m)

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Weather

Powered by Foreca

Sunday 11 October

18°C

9°C

77 %

Additional weather tips

Max wind speed: 18.0 km/h

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Frequently Asked Questions

What is the difficulty level of the Chilterns Cycleway: Rickmansworth to Princes Risborough Loop?

This loop is considered a difficult touring bicycle ride, requiring a very good level of fitness. The Chilterns are known for their undulating terrain, featuring numerous steep climbs and descents. It's not recommended for novices and requires experience cycling on roads with traffic.

What kind of terrain can I expect on this route?

The route primarily uses minor roads, but also incorporates sections of towpaths, surfaced cycle paths, and bridleways. While some parts have smooth tarmac, you'll encounter unsurfaced sections that can be rutted, muddy, and slippery due to chalk, especially after rain. A mountain bike or gravel bike might be more suitable than a road bike, particularly in wet conditions.

Where can I park or access public transport for this cycle loop?

Rickmansworth offers parking options, and Princes Risborough is an attractive market town with a railway station, making it a convenient starting or ending point. The Chilterns Cycleway is flexible, allowing you to begin at any point and ride in either direction.

Is the Chilterns Cycleway: Rickmansworth to Princes Risborough Loop dog-friendly?

While the route uses many roads and some dedicated cycle paths, sections also include bridleways and towpaths. If you plan to bring a dog, ensure they are well-behaved and can handle the varied terrain, including potential traffic and unsurfaced paths. Always keep dogs under control, especially near livestock or on busy sections.

What is the best time of year to cycle this route?

The Chilterns offer beautiful scenery year-round, but spring and summer generally provide the most pleasant cycling conditions. Autumn brings vibrant foliage. Be aware that unsurfaced sections can become very muddy and slippery after rain, particularly in winter, making the ride more challenging.

Do I need any permits or have to pay an entrance fee to cycle in the Chilterns National Landscape?

No, there are no specific permits or entrance fees required to cycle this route within the Chilterns National Landscape. It's freely accessible to the public. However, always respect private land and follow local signage.

What are some of the scenic highlights along the way?

The loop traverses the beautiful Chilterns National Landscape, offering quiet woodlands, rolling chalk hills, and wonderful open views. You'll pass by the Colne Valley Trail, Grove's Windmill, Coleshill, and enjoy descents with views like the Descent at John Hampden Monument and Descent Into Princes Risborough, Chilterns. The The Lee Village Green and Chorleywood Common Scenic Route are also notable spots.

Are there opportunities for food and drink along the route?

Yes, the route passes through charming, picturesque villages with traditional inns and pubs, providing ample opportunities to stop for refreshments. You'll find places to refuel, especially in the villages along the way.

Does this loop connect with other trails?

Yes, the route incorporates sections of several other paths. You'll find yourself on parts of the Chilterns Cycleway, Milton Route, Hampden Route, NCN National Route 57, and the Colne Valley Trail, among others.

What type of bike is best suited for this cycleway?

Given the varied terrain, which includes both smooth tarmac and potentially rutted, muddy unsurfaced sections, a gravel bike or mountain bike would be ideal. While much of it is on-road, a road bike with slick tires might struggle on the rougher or wet sections.

Is this route suitable for families or beginners?

Due to its 'difficult' grading, hilly terrain, and sections requiring experience cycling on roads with traffic, this specific loop is not recommended for beginners or young families. It's best suited for experienced touring cyclists with good fitness.

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