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Road cycling routes

South East England

Buckinghamshire

Great Missenden

Chenies Climb and Village – Penn Village loop from Great Missenden

Road cycling routes

South East England

Buckinghamshire

Great Missenden

Chenies Climb and Village – Penn Village loop from Great Missenden

Moderate

33

riders

Chenies Climb and Village – Penn Village loop from Great Missenden

02:06

47.1km

400m

Road cycling

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride. The starting point of the route is accessible with public transport.

Last updated: July 18, 2026

Tips

Your route passes through protected areas

Please check local regulations for:

Chilterns National Landscape

Waypoints

A

Start point

Train Station

1

9.53 km

Temperance Hall, Chesham

Highlight • Historical Site

A cluster of buildings that date back to the 14 Century. Always worth a visit when passing through.

Tip by

2

16.6 km

Chenies Climb and Village

Highlight (Segment) • Climb

Coming from Chesham along the River Chess this is a fairly quiet road that has nice views on the left hand side. It then climbs up into Chenies, the ascent is not too long at around 500m and averaging 5%.

Tip by

21.4 km

Crosslane Wood

Forest

4

21.8 km

Roughwood Lane

Highlight (Segment) • Cycleway

Surprisingly smooth single-track road past some lovely properties. It is predominantly downhill before levelling off towards the end of the segment if travelled from SW to NE.

Tip by

5

24.6 km

Village Green and Pond, Chalfont St Giles

Highlight • Settlement

Chalfont St Giles is a pretty village on the edge of the Chiltern Hills. With a quaint village green and duck pond, stunning timber-framed houses, as well as pubs, cafes, …

Tip by

6

35.3 km

Paul's Hill War Memorial

Highlight • Monument

7

35.6 km

Penn Village

Highlight • Settlement

Lovely scenic bit of road through Penn, pretty Chilterns village with old buildings - Penn is also the home of Mary Berry.

Tip by

8

36.5 km

Penn Common Pond

Highlight • Lake

just over the road from the red lion

Tip by

B

47.1 km

End point

Train Station

Way Types & Surfaces

Way Types

40.4 km

3.77 km

2.26 km

565 m

< 100 m

< 100 m

Surfaces

40.3 km

6.78 km

< 100 m

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Elevation

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

Highest point (180 m)

Lowest point (70 m)

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Weather

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Thursday 8 October

19°C

9°C

-- %

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