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United Kingdom
England
South East England
Buckinghamshire
Chiltern
Penn

Penn Wood and Winchmore Hill loop from Common Wood Lane

Moderate

5

runners

Penn Wood and Winchmore Hill loop from Common Wood Lane

00:56

8.78km

100m

Running

Embark on a moderate jogging route through the ancient woodlands and rolling countryside of the Chiltern Hills. This 5.5-mile (8.8 km) loop from Common Wood Lane offers a scenic experience, taking you through the beautiful Penn Wood. Here, you'll find a mix of oak, beech, ash, and cherry trees, with…

Last updated: April 23, 2026

Waypoints

A

Start point

Parking

Get Directions

1

1.75 km

Gravely Way Plantation and Two Sisters Plantation

Highlight • Viewpoint

These two plantations are part of the larger Common Wood here. Lovely views towards Hazlemere Golf Club to the west, and there is a great bench to sit on here. Otherwise, just a great forest for jogging.

Tip by

2

4.43 km

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

3

6.22 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

B

8.78 km

End point

Parking

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Way Types & Surfaces

Way Types

5.27 km

2.41 km

733 m

279 m

< 100 m

Surfaces

7.68 km

792 m

142 m

136 m

< 100 m

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Elevation

Elevation

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

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Weather

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Thursday 7 May

18°C

5°C

0 %

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Max wind speed: 12.0 km/h

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This route was planned by komoot.

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Frequently Asked Questions

How long does it typically take to jog this loop?

The Penn Wood and Winchmore Hill loop is approximately 8.8 kilometers (5.5 miles) long. For jogging, it typically takes around 55-60 minutes to complete, depending on your pace and fitness level.

Is this trail suitable for beginner joggers?

This loop is rated as moderate for jogging. While it features gentle ascents and descents, the varied terrain, including woodland paths and potentially muddy sections, requires more effort than road running. Beginners with good fitness can enjoy it, but be prepared for a good workout and varied surfaces.

Where does the trail start and where can I park?

The loop starts from Common Wood Lane. While specific parking details aren't provided, Common Wood Lane is the general access point. Look for available roadside parking or designated car parks in the vicinity, keeping local regulations in mind.

What is the terrain like on the Penn Wood and Winchmore Hill loop?

The terrain is varied, primarily consisting of woodland paths and footpaths. You can expect earth, fallen leaves, and potentially gravelly tracks. After rain, some sections may be muddy. The uneven ground engages more muscles than road running, including core muscles for balance.

What can I see along the route?

The route takes you through ancient woodlands like Penn Wood, known for its oak, beech, ash, and cherry trees. You'll also pass through Gravely Way Plantation and Two Sisters Plantation, which offer scenic views. The trail also covers countryside south of Penn Street, providing a mix of shaded forest paths and sunlit clearings. You might also pass The Plough, Winchmore Hill, a good spot for refreshments.

What is the best time of year to visit Penn Wood for jogging?

The trail is beautiful year-round. Spring offers vibrant wildflowers like bluebells and wood anemones. Autumn provides stunning foliage. Summer offers shaded paths through the woods, while winter can be serene, though some sections might be muddy. Always check local conditions before you go.

Is the Penn Wood and Winchmore Hill loop dog-friendly?

Yes, the Penn Wood area is generally dog-friendly. However, as it passes through ancient woodlands and countryside, it's always best to keep dogs under control, especially near livestock or wildlife, and to follow any local signage regarding leashing.

Do I need a permit or pay an entrance fee to access Penn Wood or the Chiltern Hills?

No, you do not need a permit or have to pay an entrance fee to access Penn Wood or the wider Chiltern Hills area for recreational activities like jogging. The network of permissive paths through Penn Wood, dedicated by the Penn Estate, makes them freely accessible.

Are there any places for refreshments near the trail?

Yes, the route passes through or near Winchmore Hill village, where you can find pubs for refreshment. The Plough, Winchmore Hill is a notable highlight along the route where you could stop.

Does this jogging route intersect with other well-known paths in the Chiltern Hills?

Yes, this route utilizes sections of several official trails. You will find yourself on parts of the Chiltern Heritage Trail, Milton Route, The Chiltern Way, Boundary Ride, and Penn House Way, among others, as you navigate the loop.

What kind of wildlife can I expect to see in Penn Wood?

Penn Wood is rich in biodiversity. While specific sightings are never guaranteed, you might spot various bird species, squirrels, and other small woodland creatures. The ancient woodlands also support a diverse range of plant life, including seasonal wildflowers.

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