Penn Wood – The Plough, Winchmore Hill loop from Winchmore Hill

Routes

Hiking trails & Routes

Penn Wood – The Plough, Winchmore Hill loop from Winchmore Hill

Easy

4.3

(6)

hikers

Penn Wood – The Plough, Winchmore Hill loop from Winchmore Hill

01:51

6.84km

90m

Hiking

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels. The starting point of the route is right next to a parking lot.

Last updated: August 6, 2026

Tips

Your route passes through a protected area

Please check local regulations for:

Chilterns National Landscape

Waypoints

Start point

Parking

Get Directions

361 m

The Squirrel Pub & Garden

Highlight • Pub

A really nice local pub with an interesting line up of ales

Tip by

530 m

Penn Wood

Highlight • Forest

This here is one of the entrances to the beautiful Penn Wood. It's a truly spectacular bit of woodland: dense, green, with lovely paths to run on. Some trees are …

Tip by

1.20 km

Bluebell Woods in Chilterns National Landscape

Highlight • Natural Monument

2.27 km

Brook Wood

Highlight • Forest

Climb to brook wood part of Penn and Common Woods managed by the woodland trust. The woods were once part of a large common called Wycombe Heath

Tip by

3.85 km

Woodland Path in Chilterns National Landscape

Highlight • Forest

4.30 km

View of the Chilterns from the Log

Highlight • Viewpoint

5.01 km

The Plough Italian Restaurant

Highlight • Other

not open Monday Tuesday

Tip by

5.02 km

The Plough, Winchmore Hill

Highlight • Cafe

Winchmore Hill goes back to the 12th century: there used to be a small settlement here supporting farms grouped around a Common and a pond (those were the days). In …

Tip by

6.03 km

Priestlands Wood

Forest

6.84 km

End point

Parking

Way Types & Surfaces

Way Types