The best family-friendly hikes and walks around Penn
4.6
(1819)
12,874
hikers
80
hikes
Family friendly hiking trails around Penn are primarily found within the Chiltern Hills, an Area of Outstanding Natural Beauty. The region is characterized by rolling hills, dense woodlands, and picturesque valleys. Many routes traverse ancient forests, offering shaded paths and varied terrain suitable for families. The landscape provides a mix of gentle ascents and relatively flat sections, making it accessible for different activity levels.
Best family friendly hiking trails around Penn
- The most popular family friendly hiking route is Penn…
Last updated: May 3, 2026
4.6
(14)
25
hikers
8.98km
02:25
110m
110m
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.
5.0
(5)
51
hikers
10.3km
02:46
120m
120m
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.
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5.0
(4)
54
hikers
10.1km
02:42
110m
110m
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.
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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Tips from the Community
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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A network of footpaths will lead you through the sensational ancient woodland of Penn Wood. The woods are dominated by beautiful oak, beech, ash, and cherry trees with an understory of bluebells, wood anemones, and other wildflowers.
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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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Frequently Asked Questions
How many family-friendly hiking trails are available around Penn?
There are over 80 family-friendly hiking routes around Penn, ranging from easy strolls to more moderate adventures. This guide focuses on routes suitable for families looking to explore the beautiful Chiltern Hills.
What kind of terrain can we expect on family hikes near Penn?
The trails around Penn, particularly in areas like Penn Wood, offer a mix of woodland paths, open fields, and gentle inclines typical of the Chiltern Hills. You'll find diverse terrain suitable for various activity levels, often featuring ancient woodlands and scenic views.
Are there any easy, short walks suitable for families with young children or strollers?
Yes, there are several easy routes perfect for families. For instance, the Holy Trinity Church, Penn – Bluebells in Penn Wood loop from Winchmore Hill is an easy 5.5 km walk with minimal elevation gain, ideal for a leisurely family outing. While not all paths are stroller-friendly, many sections of these easier routes are well-maintained.
What are some natural attractions or landmarks we can see on these family hikes?
The area around Penn is rich in natural beauty and historical sites. You can explore the ancient woodlands of Penn Wood, especially beautiful during bluebell season. Nearby attractions include the River Chess Stepping Stones and Weir, and the serene Bluebell Woodland in Chilterns National Landscape. For historical interest, consider visiting Hughenden Manor or the Marlow Suspension Bridge, which are also within reach.
Are there any circular routes recommended for families?
Many of the family-friendly trails around Penn are circular, making them convenient for day trips. A great option is the Penn Wood loop — Chiltern Hills, which offers a moderate 9 km circular hike through varied landscapes. Another good choice is the Penn Wood loop from Winchmore Hill, an easy 6.4 km circular path.
What is the best time of year to go hiking with family around Penn?
Spring and autumn are particularly beautiful seasons for family hikes around Penn. In spring, the woodlands, especially Penn Wood, are carpeted with bluebells. Autumn offers stunning fall foliage. However, the diverse terrain means that with appropriate clothing, hiking can be enjoyed year-round.
What do other hikers enjoy most about the family-friendly trails in Penn?
The area is highly rated by the komoot community, with an average score of 4.59 stars. Reviewers often praise the quiet woodlands, well-marked paths, and the overall peaceful atmosphere, making it a perfect escape for families looking to connect with nature.
Are dogs allowed on the family-friendly hiking trails around Penn?
Many trails in the Chiltern Hills, including those around Penn Wood, are dog-friendly. It's generally recommended to keep dogs on a lead, especially near livestock or in areas with wildlife, and to always clean up after your pet. Always check local signage for specific restrictions.
What are the typical difficulty levels for family hikes in this area?
The family-friendly hikes around Penn primarily fall into 'easy' and 'moderate' difficulty levels. Out of over 80 routes, 48 are easy and 30 are moderate, ensuring there's something for every family's comfort and experience level. You'll find gentle paths suitable for beginners and slightly longer routes for those seeking a bit more challenge.
Are there any routes that feature water elements like ponds or streams?
Yes, the natural landscape around Penn includes various water features. For example, the Pond in Park Wood is a lovely spot to visit. Additionally, the nearby River Chess offers picturesque views and the unique River Chess Stepping Stones and Weir, which can be an exciting point of interest for families.
Where can I find parking for these family-friendly hikes?
Many trailheads and popular starting points in the Chiltern Hills, including those near Penn Wood, offer designated parking areas. It's advisable to check specific route details on komoot for parking information relevant to your chosen trail, as availability can vary.
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