Penn Wood and Winchmore Hill loop from Common Wood Lane
Penn Wood and Winchmore Hill loop from Common Wood Lane
5
runners
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
Start point
Parking
Get Directions
1.75 km
Highlight • Viewpoint
Tip by
4.43 km
Highlight • Forest
Tip by
6.22 km
Highlight • Cafe
Tip by
8.78 km
End point
Parking
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
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Weather
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Thursday 7 May
18°C
5°C
0 %
Additional weather tips
Max wind speed: 12.0 km/h
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This route was planned by komoot.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.