The best running trails around Penn
4.6
(19)
383
runners
44
runs
Jogging around Penn offers a variety of routes through woodlands and open common land. The region features a mix of gentle inclines and relatively flat sections, suitable for different running preferences. Many trails traverse natural areas, providing a quiet environment for outdoor activity. The landscape is characterized by established woods and open spaces, offering varied scenery for runners.
Best jogging routes around Penn
- The most popular jogging route is Penn Wood and Winchmore Hill loop from Common Wood Lane,…
Last updated: April 24, 2026
5
runners
8.78km
00:56
100m
100m
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,…
37
runners
6.51km
00:41
60m
60m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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28
runners
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
25
runners
5.36km
00:34
60m
60m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
16
runners
10.9km
01:09
50m
50m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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Tips from the Community
Stunning little pond on Penn Common with a charming pub nearby. A great place to stop for a break, or just to enjoy the view as you ride past. Especially beautiful as the sun is going down.
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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.
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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 1958, the pond was filled in, but luckily the Common is still here, on the edge of what used to be Wycombe Heath: 4,000 acres of open common land providing grazing for animals and material for firewood. It's a lovely hamlet. There is a great information board, from which you can learn more about the history of the place. And a good pub in a village can never be wrong! - so make sure you make a stop at The Plough!
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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 ancient: one, thought to be the oldest in the wood, is the Holey Oak (there is a hole in the trunk...), and the other is the Penn Pollard, memorable for its very open crown. You're in for a treat here!
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Great pub in Winchmore Hill. A good stop off point, whether you want a coffee, a beer or some pizza!
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Note: despite the title, there is no coffee for sale here!
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Frequently Asked Questions
How many running routes are available around Penn?
There are over 40 dedicated jogging routes around Penn, offering a diverse range of experiences. These include 6 easy routes, 37 moderate routes, and 1 more challenging option, ensuring there's something for every runner.
Are there any easy running trails suitable for beginners or a relaxed jog?
Yes, Penn offers several easy running trails. One popular option is the Sheep Washing Pond loop from Beaconsfield, which is an easy 3.1-mile (4.9 km) path, perfect for a gentle run or a family outing.
What kind of terrain can I expect on the jogging routes in Penn?
The running routes in Penn primarily feature woodlands and open common land. You'll find a mix of gentle inclines and relatively flat sections, providing varied scenery and suitable conditions for different running preferences. Many trails traverse natural areas, offering a quiet environment.
Are there any circular running routes in the Penn area?
Absolutely! Many of the running routes around Penn are circular, allowing you to start and finish in the same location. For example, the popular Penn Wood and Winchmore Hill loop from Common Wood Lane is a moderate 5.5-mile (8.8 km) circular trail.
What do other runners say about the trails in Penn?
The running routes in Penn are highly regarded by the komoot community, holding an average rating of 4.5 stars from over 20 reviews. Runners often praise the quiet woodlands, varied terrain, and the overall pleasant environment for outdoor activity.
Can I find any scenic viewpoints or natural attractions along the running routes?
Yes, the routes often pass by natural attractions. For instance, the The Red Lion, Penn – Penn Common Pond loop from Gomm Valley circles Penn Common Pond, offering pleasant waterside views. Other routes may lead you past highlights like Shardeloes Lake or through areas like Spade Oak Nature Reserve.
Are there any historical or interesting landmarks to see while running?
While jogging around Penn, you might encounter various points of interest. Some routes are near historical sites like Hughenden Manor or charming religious buildings such as All Saints' Church, Marlow, adding a cultural element to your run.
Are there any running routes that pass through estates or specific areas?
Yes, some routes take you through notable local areas. The The Beaconsfield Café – Oakwood Estates, Beaconsfield loop from Beaconsfield is a popular 5.0-mile (8.0 km) trail that leads through the scenic Oakwood Estates.
What is the typical duration for a running route in Penn?
The duration of running routes in Penn varies depending on the distance and your pace. For example, a moderate 5.5-mile (8.8 km) route like the Penn Wood and Winchmore Hill loop typically takes about 56 minutes to complete.
Are there any routes that offer a mix of woodland and open spaces?
Many of the routes in Penn provide a great balance of woodland and open common land. This variety ensures a dynamic running experience, with shaded sections through established woods and expansive views across open spaces.
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