The best dog-friendly hikes and walks around Penn
4.6
(1973)
13,439
hikers
45
hikes
Dog friendly hiking trails around Penn are characterized by a landscape of rolling hills and extensive woodlands, offering a variety of routes for outdoor enthusiasts. The region features a mix of open fields, forested paths, and gentle ascents, providing accessible terrain for hikers and their dogs. This area is known for its natural beauty, with many trails winding through picturesque countryside and offering views of the local topography.
Best dog friendly hiking trails around Penn
- The most popular dog friendly hiking route is Penn Wood – Penn Wood loop from Penn, a 6.4 miles (10.3 km) trail that takes about 2 hours 45 minutes to complete. This moderate route features varied woodland paths and gentle hills.
- Another top favourite among local hikers is Holy Trinity Church, Penn – Penn Wood loop from Winchmore Hill, an easy 2.5 miles (4.0 km) path. This shorter trail offers a pleasant walk through Penn Wood, suitable for a quick outing.
- Local hikers also love the Penn Wood – Holy Trinity Church, Penn loop from Coleshill, a 4.4 miles (7.1 km) trail leading through mixed woodlands and open countryside, often completed in about 1 hour 50 minutes.
- Hiking around Penn is defined by its extensive woodlands, rolling hills, and open fields. The network offers options for various ability levels, from easy strolls to more moderate hikes.
- The routes in Penn are highly rated by the komoot community with an average score of 4.6 stars from more than 1,800 reviews. More than 12,000 hikers have used komoot to explore Penn's varied terrain.
Last updated: July 10, 2026
5.0
(5)
51
hikers
10.3km
02:46
120m
120m
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.
5.0
(1)
33
hikers
4.04km
01:03
30m
30m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
5
hikers
7.15km
01:51
40m
40m
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!
1
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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!
2
0
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.
2
0
The water trough is about 10 meters off the path have faith
0
0
Great pub in Winchmore Hill. A good stop off point, whether you want a coffee, a beer or some pizza!
0
0
Frequently Asked Questions
How many dog-friendly hiking trails are available around Penn?
There are over 45 dog-friendly hiking trails around Penn, offering a wide variety of experiences for you and your canine companion. These routes range from easy strolls to more challenging hikes, ensuring there's something for every fitness level.
Are there easy dog-friendly walks suitable for beginners or families with dogs?
Yes, Penn offers many easy dog-friendly walks perfect for beginners or families. For a gentle and scenic option, consider the Holy Trinity Church, Penn – Penn Wood loop from Winchmore Hill. This route is approximately 4 km long with minimal elevation gain, making it ideal for a relaxed outing.
What kind of terrain can I expect on dog-friendly trails around Penn?
The dog-friendly trails around Penn primarily feature woodland paths, often through areas like Penn Wood. You can expect varied terrain including compacted earth, some gravel sections, and gentle slopes. Many routes are loops, providing a diverse experience without retracing your steps.
Are there any longer or more challenging dog-friendly hikes for experienced hikers?
For those seeking a longer and more challenging adventure with their dog, the Penn Wood – Penn Wood loop from Penn is an excellent choice. This moderate route covers over 10 km with a noticeable elevation gain, offering a good workout amidst beautiful scenery.
What do other hikers say about the dog-friendly trails in Penn?
The dog-friendly trails around Penn are highly regarded by the komoot community, with an average rating of 4.58 out of 5 stars. Reviewers frequently praise the quiet woodlands, well-maintained paths, and the overall peaceful atmosphere, making them perfect for walks with dogs.
Can I find circular dog-friendly walks in the Penn area?
Absolutely! Many of the dog-friendly routes around Penn are circular, allowing you to start and end at the same point without repeating sections. An example is the Penn Wood – Holy Trinity Church, Penn loop from Coleshill, which offers a pleasant 7 km loop through the local landscape.
Are there any natural attractions or points of interest to see along the dog-friendly trails?
While hiking with your dog around Penn, you can discover several charming natural spots. Keep an eye out for beautiful water features like Shardeloes Lake or Penn Common Pond, which offer picturesque views and a chance for your dog to enjoy the surroundings (check local rules for water access).
What historical or man-made landmarks can I visit near the dog-friendly hiking areas?
Beyond the natural beauty, the Penn area also features interesting historical and man-made landmarks. You might encounter sites like All Saints' Church, Marlow, or the impressive Marlow Suspension Bridge. Always ensure dogs are permitted in the immediate vicinity of these attractions.
What is the best time of year to go dog-friendly hiking around Penn?
Pennsylvania, including the Penn area, offers excellent hiking opportunities throughout the year. Spring brings lush greenery and blooming wildflowers, while autumn showcases stunning fall foliage. Summer is great for longer days, and even winter can be beautiful for a crisp walk, though some trails might be muddy or icy. Always check local conditions before heading out.
Are there specific considerations for hiking with dogs in the Penn area?
When hiking with your dog around Penn, always ensure they are kept on a leash, especially in areas with wildlife or near roads. Carry enough water for both yourself and your dog, and remember to pick up after your pet. Be mindful of other trail users, including cyclists and other hikers.
Are there any trails around Penn that offer views of lakes or ponds?
Yes, several trails in the Penn area provide scenic views of local water bodies. You can find routes that pass by Shardeloes Lake or Penn Common Pond, offering tranquil spots for a break and beautiful photo opportunities with your dog.
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