Chess Valley Circular: Chesham Loop
Chess Valley Circular: Chesham Loop
7
runners
Chess Valley Circular: Chesham Loop
00:56
8.28km
100m
Running
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 343 feet (105 metres), and you can expect to complete it in about 55 minutes. As you jog, you will…
Last updated: April 23, 2026
Tips
Your route passes through protected areas
Please check local regulations for:
Waypoints
Start point
Parking
Get Directions
1.33 km
Chiltern Heritage Trail Countryside Path Near Hollybush Farm
Highlight (Segment) • Viewpoint
Tip by
5.94 km
River Chess Stepping Stones and Weir
Highlight • Structure
Tip by
7.87 km
Chesham Clock Tower
Highlight • Monument
Tip by
8.28 km
End point
Parking
Way Types & Surfaces
Way Types
2.80 km
1.52 km
1.46 km
1.16 km
1.15 km
121 m
< 100 m
Surfaces
2.51 km
1.83 km
1.16 km
1.05 km
925 m
782 m
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Elevation
Highest point (180 m)
Lowest point (90 m)
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Weather
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Wednesday 20 May
22°C
8°C
0 %
Additional weather tips
Max wind speed: 13.0 km/h
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This route was planned by komoot.
Frequently Asked Questions
How long does it typically take to jog the Chess Valley Circular: Chesham Loop?
On average, jogging this loop takes about 55 minutes. This duration can vary based on your pace and how often you pause to enjoy the scenic views.
What is the terrain like on the Chess Valley Circular: Chesham Loop?
The trail features a varied terrain of dirt tracks, fields, and some narrow paths, winding through rolling countryside. It can be quite muddy, especially after rain, so we recommend wearing footwear with good grip.
Is the Chess Valley Circular: Chesham Loop suitable for beginner joggers?
While generally considered a moderate walk, jogging this loop requires a good level of fitness. It includes three climbs with a total ascent of approximately 105 meters (560 feet) and varied terrain, which can be challenging for beginners.
What kind of wildlife and plants can I expect to see along the route?
The Chess Valley is rich in biodiversity. You might spot kingfishers, water voles, and brown trout in the River Chess. In early summer, Cowcroft Wood nature reserve, which is along the route, is known for its bluebells and wild orchids.
What are the best times of year to jog this trail?
The trail is enjoyable year-round, but spring and early summer offer the chance to see bluebells and orchids. Autumn provides beautiful foliage. Be prepared for potentially muddy conditions, especially after rain, regardless of the season.
Are there any notable landmarks or viewpoints along the Chess Valley Circular: Chesham Loop?
Yes, the route offers several points of interest. You'll pass the Chiltern Heritage Trail Countryside Path Near Hollybush Farm, the picturesque River Chess Stepping Stones and Weir, and the historic Chesham Clock Tower.
Does the trail intersect with other well-known paths?
Yes, the route incorporates sections of several other paths, including the Chiltern Heritage Trail, the Chess Valley Walk, and the Harding Route.
Is the Chess Valley Circular: Chesham Loop dog-friendly?
Yes, the trail is generally dog-friendly. However, as it passes through fields and near wildlife habitats, dogs should be kept on a leash, especially when livestock are present or during nesting seasons.
Do I need a permit or pay an entrance fee to access the trail or the Chilterns National Landscape?
No, there are no permits or entrance fees required to access the Chess Valley Circular: Chesham Loop or the surrounding Chilterns National Landscape. It is freely accessible to the public.
Where can I park to access the Chess Valley Circular: Chesham Loop?
The trail starts and ends in Chesham. Parking is available in various public car parks within Chesham town center, which are typically a short walk from the trailhead.
Are there any cafes or pubs near the trail for refreshments?
Yes, as the loop starts and ends in Chesham, there are several cafes, pubs, and shops in the town center where you can find refreshments before or after your jog.