4.6
(49)
2,694
runners
272
runs
Jogging around Chiltern offers a diverse landscape characterized by a dramatic chalk escarpment, providing panoramic views across rolling hills and valleys. The region features extensive ancient woodlands, some with trees over 800 years old, offering shaded and tranquil running paths. Rare chalk streams, such as the River Chess, and chalk grasslands also contribute to the varied terrain, creating a dynamic environment for runners.
Last updated: April 24, 2026
7
runners
8.28km
00:56
100m
110m
The Chess Valley Circular: Chesham Loop invites you to a moderate jogging experience through the attractive Buckinghamshire countryside. This route covers 5.1 miles (8.3 km) with an elevation gain of…
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,…

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120
runners
10.8km
01:09
120m
120m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
4.0
(1)
67
runners
46.7km
05:17
510m
510m
Hard run. Very good fitness required. Mostly accessible paths. Some sure footedness required.
143
runners
10.8km
01:08
100m
100m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
37
runners
6.51km
00:41
60m
60m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
4.0
(1)
31
runners
5.83km
00:41
70m
70m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
32
runners
7.59km
00:48
80m
80m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
29
runners
18.2km
02:02
210m
210m
Hard run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
27
runners
11.3km
01:13
90m
90m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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Popular around Chiltern
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Truly a village that is steeped in olde worlde charm. Some great restaurants and pubs. The history seeps through its pores. The Kings Arms Hotel & The Crown Hotel & Pub in Amersham, was the set of a scene the 4 Weddings and a funeral movie.
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Really nice gentle climb up the hill on a great surface.
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Pednor House is a Grade II listed building in Chartridge, Buckinghamshire. Originally a 17th-century farmhouse, it was enlarged in 1910 under the architects Forbes and Tate in the Arts and Crafts style. The house is a large U-shaped structure with a cylindrical dovecote and stands in a beautiful setting. The grounds were originally designed by Gertrude Jekyll.
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When walking from east to west there are three benches seperated a few hundred meters apart (this is the first). All have a great view and are nice places for a rest.
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Beautiful town and perfect to finish off hike/ walking trail, great choice of Café, try sitting outside @ Amersham House for coffee/ brunch
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Lovely lake and doesn’t look like man made at all and would recommend Boots for the path and Park specially if there has been rain over last few days
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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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The Chilterns offer a diverse landscape, characterized by a dramatic chalk escarpment with panoramic views, ancient woodlands providing shaded and tranquil paths, and rare chalk streams like the River Chess. You'll find a mix of gently rolling paths, often with a 'springy surface' from beech nuts in the woodlands, and some routes traversing chalk grasslands. This varied terrain provides an engaging environment for runners.
Yes, the Chilterns offer a good selection of routes suitable for beginners. While many routes are moderate, there are approximately 30 easy running trails available. These typically feature gentler gradients and well-maintained paths, perfect for those new to trail running or looking for a relaxed jog.
The Chilterns are rich in natural beauty and historical sites. You might encounter rare chalk streams, ancient woodlands, and chalk grasslands. Specific points of interest include the River Chess Stepping Stones and Weir, the scenic Shardeloes Lake, and historical sites like Cholesbury Camp Iron Age Hill Fort. Keep an eye out for red kites soaring overhead, a common sight in the region.
Absolutely. For experienced runners seeking a challenge, the Chilterns offer approximately 30 difficult routes. These trails often feature more significant elevation changes and longer distances, providing a demanding workout amidst the region's beautiful, varied terrain. An example of a longer route is the Chesham Clock Tower loop from Amersham, which spans over 45 km.
The Chilterns are highly rated by the komoot community, with an average score of 4.7 stars from over 50 reviews. Runners frequently praise the diverse landscapes, from rolling hills and ancient woodlands to picturesque chalk streams. The well-maintained paths and varied elevation also contribute to a highly enjoyable and engaging running experience.
Yes, many of the running routes in the Chilterns are circular, offering convenient starting and ending points. For instance, the Pednor House – Herbert's Hole Road loop from Ballinger Bottom and the Chesham Clock Tower loop from Chesham are popular circular options, allowing you to explore the scenery without retracing your steps.
The Chilterns are renowned for their extensive ancient woodlands, some featuring trees over 800 years old. Many running routes, such as the Penn Wood and Winchmore Hill loop from Common Wood Lane, wind through these shaded and tranquil areas, offering a unique and often 'springy' surface underfoot.
Yes, the Chilterns are home to rare chalk streams, which provide beautiful routes. The Chess Valley Circular: Chesham Loop is a prime example, following the scenic River Chess through picturesque landscapes, allowing runners to enjoy the clear, sparkling waters.
Running routes in the Chilterns vary significantly in length to suit different preferences. You can find shorter loops, such as the Liberty Tomb loop from Little Chalfont, which is around 5.8 km, to much longer, more challenging trails. The average route length is well-suited for a good workout, with many moderate options between 5 km and 15 km.
The dramatic chalk escarpment of the Chilterns provides numerous opportunities for stunning panoramic views across rolling hills and valleys. While specific viewpoints vary by route, many trails offer elevated sections where you can pause and enjoy the expansive scenery, particularly in areas like Coombe Hill.
While specific routes with integrated pub stops are not explicitly listed, the Chilterns region is dotted with charming villages and traditional pubs. Many routes pass near or through villages where you can find establishments like The Royal Standard of England, making it possible to combine your run with a refreshing stop.
The Chilterns offer a great running experience year-round, but each season has its charm. Spring brings blooming wildflowers, while autumn showcases vibrant foliage in the ancient woodlands. Summer provides pleasant conditions for shaded runs, and even winter can be beautiful, though some paths might be muddy. Always check local conditions before heading out.
Yes, the Chilterns feature beautiful natural settings, including lakes. The Shardeloes Lake loop from Little Missenden is a popular choice, offering a scenic trail that leads through varied landscapes around the picturesque Shardeloes Lake.


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