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Hiking trails & Routes
United Kingdom
England
South East England
Buckinghamshire
Chiltern
Great Missenden

Prestwood to Little Hampden loop — Chiltern Hills

Moderate

4.3

(8)

20

hikers

Prestwood to Little Hampden loop — Chiltern Hills

02:22

8.42km

170m

Hiking

Embark on the Prestwood to Little Hampden loop, a moderate hike through the picturesque Chiltern Hills. This 5.2-mile (8.4 km) route, which takes about 2 hours and 22 minutes to complete, features 569 feet (173 metres) of elevation gain across its undulating terrain. You will traverse ancient woodlands, rolling green chalk hills, and open fields, enjoying scenic vistas across the countryside. Be prepared for some unpaved sections and a steep descent into the unique Hampden Bottom Valley; the path can become muddy after rain. In spring, the woodlands are often carpeted with vibrant bluebells.

While planning your visit, remember that this trail is generally considered moderate and requires good fitness. The paths are mostly accessible, but the varied ground conditions mean sturdy footwear is advisable, especially after wet weather. The route is suitable for most skill levels, but the undulating terrain and potential for mud should be taken into account. There are no specific mentions of trailhead access, parking, or public transport in the available information, so you may want to research local options before heading out.

This loop offers more than just natural beauty; it is rich in history and unique geological features. You can visit the John Hampden Monument, an 1863 memorial to a key figure in the English Civil War. The isolated 13th-century Little Hampden Church, with its 15th-century wall paintings, is another highlight. The Hampden Bottom Valley itself is a notable feature, formed during the last Ice Age and retaining an untouched feel, bypassed by modern transport routes. The trail is part of the Chiltern Hills Area of Outstanding Natural Beauty and connects to sections of the South Bucks Way and Chiltern Heritage Trail.

Last updated: April 23, 2026

Tips

Your route passes through a protected area

Please check local regulations for:

Chiltern Hills AONB

Waypoints

A

Start point

Parking

Get Directions

1

1.83 km

John Hampden Monument (Ship Money Memorial)

Highlight • Monument

This monument to John Hampden is also known as the Ship Money Memorial and was erected in 1863. John “the Patriot” was MP for Wendover and Buckinghamshire and a parliamentary opponent of Charles I. His refusal to pay the unpopular ship money tax on some of his land in 1637 helped trigger the Civil War. He was mortally wounded and died in 1643 after fighting for the Parliamentary army.

Tip by

2

4.38 km

Little Hampden Church

Highlight • Religious Site

Little Hampden Church is a picturesque 12th-century parish with a distinctive 15th-century timber porch. In the nave, you can observe wall paintings from the 13th-15th centuries. There are also many 15th and 16th-century figures and stained-glass from the 19th and 20th centuries. Little Hampden Church is Grade I-listed.

Tip by

3

6.47 km

Hampden Bottom Valley

Highlight • Gorge

The Chilterns topography, including the Hampden Bottom valley, was largely formed during the last Ice Age by the action of meltwater on permafrost land. Unlike the Chilterns valleys on either side (West Wycombe/Princes Risborough and Great Missenden/Wendover) this valley’s northern end was not deeply eroded and is left hanging, marked by the steep descent of the road from Chequers down to Butlers Cross. As a result, major/designated roads and railways have bypassed the valley. The valley bottom and surrounding hillsides still have an air of rather being left behind by the modern world.
nationaltrust.org.uk/chilterns-countryside/trails/the-hampdens-trail

Tip by

B

8.42 km

End point

Parking

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Way Types & Surfaces

Way Types

5.00 km

2.22 km

930 m

147 m

106 m

Surfaces

4.11 km

2.64 km

767 m

762 m

123 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 (220 m)

Lowest point (150 m)

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Weather

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Today

Wednesday 15 July

28°C

13°C

0 %

Additional weather tips

Max wind speed: 18.0 km/h

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