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Hiking trails & Routes
United Kingdom
England
South East England
Buckinghamshire
Chiltern
Amersham

Chess Valley loop from Amersham — Chiltern Hills

Hard

4.8

(10)

52

hikers

Chess Valley loop from Amersham — Chiltern Hills

05:19

20.2km

180m

Hiking

Embark on the Chess Valley loop from Amersham, a difficult hike through the picturesque Chiltern Hills. This challenging route covers 12.5 miles (20.2 km) with 576 feet (175 metres) of elevation gain, typically taking around 5 hours and 18 minutes to complete. You will experience varied terrain, from tranquil riverside paths along the sparkling River Chess to narrow dirt tracks and open fields. Keep an eye out for wildlife like kingfishers and water voles as you pass charming village cottages and sheep farms, enjoying sweeping valley views, especially from elevated points overlooking Latimer Park Farm.

Planning your visit requires some preparation, as the trail can become extremely muddy, particularly after rain. You will definitely want waterproof hiking boots with good grip; some sections might even call for wellington boots. The route is easily accessible from London via the Metropolitan line, making it a popular escape for city dwellers seeking a refreshing outdoor experience.

This trail is rich in history and natural beauty, following one of the Chilterns' famed chalk streams, the River Chess. You will encounter historical elements like the grand Latimer Estate, which dates back to the 12th century and played a role in WWII, as well as a Roman farm villa at Latimer. While generally well-marked with a distinctive blue and white fish symbol, some sections may require careful navigation, so it is wise to carry detailed instructions or a map.

Last updated: April 23, 2026

Tips

Your route passes through protected areas

Please check local regulations for:

Chiltern Hills AONB

Waypoints

A

Start point

Train Station

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1

9.76 km

Sheep Fields in Chilterns National Landscape

Highlight • Natural

Stroll through beautiful open fields filled with friendly sheep. This is a great place for the kids to have a run around, just make sure to keep any pups on a leash.

Tip by

2

10.6 km

De Vere Latimer Estate

Highlight • Monument

Enjoy scenes of a historic Chiltern Hills country house framed with grazing sheep, rolling hills, and sensational valley views.

The house dates back to the 16th century and was once used as a royal residence. Today, the house is used to host events and parties and is also open as a hotel.

Tip by

3

10.7 km

View of the Chess Valley

Highlight • Viewpoint

With Latimer House behind, you can look down the valley at the river Chess and Latimer Park Farm. On the day we passed through the fields were *full* of sheep, but I can’t guarantee they’ll be there for you.

Tip by

4

14.8 km

There is a lovely little weir on the River Chess here that's worth stopping by. Also, on the same pond, you will see stepping stones (called Steps of Heaven by some) if you'd like to walk across!

A good few years ago, I used to live in the street right next to these ponds, so I can vouch for the fact that this is a great place to spend some time at, particularly in the summer.

Tip by

B

20.2 km

End point

Train Station

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Way Types & Surfaces

Way Types

7.18 km

6.17 km

2.56 km

1.91 km

1.16 km

1.00 km

214 m

Surfaces

10.7 km

3.13 km

2.95 km

2.70 km

749 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 (170 m)

Lowest point (70 m)

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Weather

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Monday 18 May

17°C

9°C

90 %

Additional weather tips

Max wind speed: 28.0 km/h

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This route was planned by komoot.

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