4.6
(1959)
13,404
hikers
87
hikes
Easy hiking trails around Penn traverse a landscape characterized by dense woodlands and gentle, rolling hills. The area offers a variety of paths suitable for leisurely walks and family outings. These routes often lead through historic villages and natural reserves, providing accessible outdoor experiences.
Last updated: June 30, 2026
4.9
(8)
46
hikers
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
4.3
(6)
21
hikers
6.84km
01:51
90m
90m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

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5.0
(2)
33
hikers
6.86km
01:51
80m
80m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
5.0
(1)
18
hikers
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
4.3
(3)
12
hikers
5.35km
01:27
80m
80m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
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Netherland Wood, Brown's Wood and Great Beard's Wood make up this large area of woodland northeast of Knotty Green. There are a series of footpaths crossing the woods, offering peaceful strolls sheltered from the weather and sun.
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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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This church was founded over 800 years ago. A number of elements in the church are very old (e.g., the nave is from the 12th century), but the Chapel was rebuilt in the 18th century. Of particular note is the "Penn Doom", one of just five surviving wooden tympanums in the UK. ("Tympanum" is the space between the round arch and the lintel over a doorway, found in many churches.) If you are one for churches, this one is a definite must, and if not... well, one's gotta start sometime!
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Penn Wood is a large, ancient woodland situated in the Chiltern Hills not too far from Amersham. The woods are beautiful to stroll around any time of the year, however, if visiting in the spring months, you'll be afforded a beautiful display of seasonal bluebells.
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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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There are over 50 easy hiking trails around Penn, offering a variety of paths through dense woodlands and gentle, rolling hills. In total, the area features 82 routes for different ability levels.
The trails around Penn are highly rated by the komoot community, with an average score of 4.7 stars from nearly 300 reviews. Hikers often praise the serene woodland scenery, the gentle ascents, and the well-maintained paths that make for enjoyable and accessible outdoor experiences.
Yes, many of the easy trails around Penn are perfect for families. Routes like the Holy Trinity Church, Penn – Bluebells in Penn Wood loop from Winchmore Hill, known for its seasonal bluebell displays, offer pleasant walks suitable for all ages. The gentle terrain and varied woodland scenery make for an enjoyable family outing.
Absolutely. Many of the easy routes in Penn are designed as loops, providing a convenient way to explore the area without retracing your steps. Popular options include the Penn Wood loop from Winchmore Hill and the View of Penn Bottom at Sunset – Netherland Wood Trails loop from Beaconsfield, both offering varied scenery and gentle ascents.
The easy hiking trails around Penn often lead through beautiful natural settings. You can discover highlights such as the Bluebell Woodland in Chilterns National Landscape, especially vibrant in spring, and tranquil spots like the Pond in Park Wood. These routes showcase the region's dense forests and natural reserves.
Yes, the area around Penn is rich in history. You might encounter sites like The Brick and Tile Works or the impressive Burnham Beeches. Further afield, you can visit Hughenden Manor or the historic Marlow Suspension Bridge, which are accessible from some of the longer routes or nearby areas.
Easy hikes around Penn typically range from 1 hour 25 minutes to 1 hour 45 minutes. For example, the Holy Trinity Church, Penn – Bluebells in Penn Wood loop from Winchmore Hill takes about 1 hour 25 minutes, while the View of Penn Bottom at Sunset – Netherland Wood Trails loop from Beaconsfield is often completed in about 1 hour 45 minutes.
Many of the woodland trails and paths around Penn are suitable for dogs, especially those that traverse open countryside and forests. It's always recommended to keep dogs on a lead, especially near livestock or in nature reserves, and to check specific trail regulations before you go.
Penn offers enjoyable hiking experiences throughout the year. Spring is particularly beautiful with bluebell displays in woodlands. Summer provides lush greenery and pleasant temperatures. Autumn brings vibrant foliage, and even winter offers crisp, quiet walks through the bare woods, provided conditions are safe.
Yes, some routes are designed to pass by or start near local establishments. For instance, the The Plough, Winchmore Hill – Brook Wood loop from Penn suggests a route that incorporates a local pub, offering a perfect opportunity to relax and refuel after your walk.
While many trails are well-known, exploring routes like the Priestlands Wood loop from Coleshill can offer a quieter experience through charming woodlands. These less-trafficked paths provide a sense of discovery while still being easily accessible.


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