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Chesham walks
Across the Chilterns: Chesham to Wendover
Association / Club / Walk leader
10.44 mi
+764 ft
-699 ft
5h 30
Moderate
Departure from Chesham (Buckinghamshire)
A linear walk from Chesham to Wendover climbing to the top of the Chiltern escarpment with spectacular views over the Oxford plains from the top of Coombe Hill. The Chiltern Hills are the main point of interest - you walk up one side, to the shoulder, then back down to civilisation. The physical nature of the geography and geology makes this walk feel bigger than it is.
A Ley Hill Circular
3.82 mi
+167 ft
-135 ft
1h 55
Easy
Departure from Latimer and Ley Hill (Buckinghamshire)
This stile free walk to the east of Chesham explores the network of paths in beautiful rolling countryside. There are lovely views of the Chess valley and the walk passes Cowcroft Wood nature reserve where bluebells and wild orchids can be found during the early summer.
26km run from Amersham Station
Visorando Member16.38 mi
+617 ft
-617 ft
8h 05
Easy
Departure from Amersham (Buckinghamshire)
Easy, albeit long, 26km run through the Chiltern hills. Note there is a nice coffee shop in the church in Little Kingshill, which can be good stop for refreshment along the way (not open on Sundays). Hyde Heath is also good for a pitstop, so you don't need to carry much water/snacks. If you do it in the direction indicated, there is not much climbing at the end. Otherwide, the hill from the River Misborne into Amersham-on-the-hill is tough at the end of a long run.
Captain's Wood
5.39 mi
+381 ft
-390 ft
2h 50
Easy
Departure from Chartridge (Buckinghamshire)
This wonderful, varied walk takes in ancient field patterns and hedges, old earthworks and the home of a famous author, as well as looking at the work carried out by Chiltern Society volunteers.
Chiltern 60k bike ride
39.28 mi
+2,382 ft
-2,359 ft
7 hrs
Very difficult
Departure from Chartridge (Buckinghamshire)
This is a beautiful mostly scenic ride around the Chilterns, although high elevation and a couple of monstrous hills to overcome. This tour starts at Chesham and gives a beautiful tour of the surrounding areas and towns.
Amersham Family Walk
3.13 mi
+43 ft
-46 ft
1h 30
Easy
Departure from Amersham (Buckinghamshire)
This leisurely linear walk takes you along the edge of Shardeloes Lake with its many water birds and past the imposing Shardeloes Manor. It continues through fields by the River Misbourne with an optional extension to the picturesque village of Little Missenden with its ancient church, manor house, and pubs.
Old Amersham to Chipperfield
8.09 mi
+489 ft
-358 ft
4h 10
Easy
Departure from Amersham (Buckinghamshire)
A tough walk through the rolling Chiltern Hills taking in Chess Valley Walk, Chilterns Way and Hertfordshire Way. Starts in Old Amersham, near St Mary's Church. Big climb up to pass Martyrs Memorial on the hill above Amersham, then through Chiltern Forest, Latimer, Flaunden and Chipperfield Common to finish at the Two Brewers Inn, Chipperfield.
Ballinger and The Lee
5.07 mi
+187 ft
-203 ft
2h 30
Easy
Departure from Great Missenden (Buckinghamshire)
A mixed route on footpaths and tracks through fields and woodland, visiting the picturesque village green at The Lee.
River Chess highlights : Chalfont & Latimer, Chiltern AONB
5.66 mi
+236 ft
-226 ft
2h 50
Easy
Departure from Little Chalfont (Buckinghamshire)
This circular walk is very peaceful and part of the Chess Valley Walk. The short walk from Chalfont & Latimer station will take you through neat Metroland streets, with mock 1930’s Tudor jostling with Art Deco suburban dwellings within easy reach of London and the countryside. Hemmed in on all sides by the pressures of London and urban overspill, the charming Chess Valley is a haven of solitude in outstanding Chilterns countryside.
Chalfont and Latimer to Chorleywood via Flaunden
11.76 mi
+712 ft
-833 ft
6h 00
Moderate
Departure from Little Chalfont (Buckinghamshire)
This Chilterns walk takes in parts of the Chess Valley walk at the start and end of the route and a section of the Chiltern Way in between. There is a variety of scenery with undulating landscapes, pastoral scenes of grazing animals, fields of wild flowers in summer, a cricket pitch, a golf course, a quarry, two churches and the shallow chalk stream of the River Chess.
Sarratt Bottom and Chenies from Little Chalfont
6.69 mi
+236 ft
-226 ft
3h 15
Easy
Departure from Little Chalfont (Buckinghamshire)
This walk along the River Chess starts from Little Chalfont in Buckinghamshire and walks east through pleasant surroundings before turning west to Chenies and a return to the start.
Chess Valley Route, Chilterns
5.95 mi
+328 ft
-348 ft
3h 00
Moderate
Departure from Little Chalfont (Buckinghamshire)
This stile-free walk explores the picturesque Chess Valley and the pretty village of Chenies with its Tudor manor house, 15th century church and village green. It climbs to Church End, Sarratt, passing through the churchyard of the 12th century church. There are fine views of the valley and the River Chess.
Cholesbury Camp, Chilterns
3.87 mi
+253 ft
-230 ft
2h 00
Easy
Departure from Cholesbury-cum-St Leonards (Buckinghamshire)
The highlight is a visit to Cholesbury Camp, a well-preserved Iron Age hillfort now managed by the Chiltern Society. You will also discover a fascinating history that includes historic buildings, a generous vicar and a local hero who fought at the Battle of Trafalgar.
Cholesbury Hillfort, Grim's Ditch & The Ridgeway
6.73 mi
+312 ft
-289 ft
3h 20
Moderate
Departure from Cholesbury-cum-St Leonards (Buckinghamshire)
This walk explores the countryside surrounding the Cholesbury Hillfort taking in Dundridge Manor, attractive fields, beech woods, village churches, a section of the Ridgeway National Trail and the enigmatic Grim's Ditch.
Little Hay and Box Moor Trust
4.99 mi
+279 ft
-272 ft
2h 30
Moderate
Departure from Bovingdon (Hertfordshire)
A great circular walk combining canal, chalk stream and woodland, along with some lovely scenic views over the Bulbourne Valley.
The route is described from Little Hay Golf Club, but it is easy to join at Waypoint 7, from the south side of Hemel or the Railway Station.
A Penn Circuit, Chilterns
5.75 mi
+243 ft
-233 ft
2h 50
Easy
Departure from Penn (Buckinghamshire)
An undulating walk through woodland and arable farmland, via Penn House Estate, Common Wood and Penn Wood.
Berkhamsted to Rickmansworth
14.36 mi
+30 ft
-184 ft
6h 40
Difficult
Departure from Berkhamsted (Hertfordshire)
This is the fourth stage of the multi-day route "Railways and Waterways, between Oxford and London".
Following the River Bulbourne, then the River Gade along the valley, there is plenty to see on this walk, from the narrowboats, historic locks and bridges and the oldest mechanised paper mill in the world, to nature reserves and the popular Cassiobury Park.
Berkhamsted to Frithsden with the Devil's Own
6.27 mi
+417 ft
-420 ft
3h 15
Moderate
Departure from Berkhamsted (Hertfordshire)
A walk through lovely Chiltern scenery with lots of interest on the way - a Norman Castle, WW1 trenches, a canal and more.
Berkhamsted Common
4.91 mi
+377 ft
-364 ft
2h 35
Easy
Departure from Berkhamsted (Hertfordshire)
This walk takes in some great views of the valleys and woodland to the north and east of the historic town of Berkhamsted. You pass the remains of Berkhamsted Castle, visit a nature reserve and walk through the ancient woods of Frithsden Beeches.
Holmer Green to Coleshill via Penn Wood
6.88 mi
+171 ft
-194 ft
3h 20
Moderate
Departure from Little Missenden (Buckinghamshire)
This is a delightful walk from Holmer Green (located between High Wycombe and Amersham) through Chilterns woodland, fields and tracks to Coleshill All Saints Church, where there are benches in the churchyard for a picnic. Return the same way.
Chipperfield to St Albans Abbey Station
9.00 mi
+404 ft
-574 ft
4h 30
Easy
Departure from Chipperfield (Hertfordshire)
Starts at Two Brewers Inn, Chipperfield. Passes thru' Kings Langley where we join the Grand Union Canal for a short distance. Then thru' Bedmond & Potters Crouch before descending past the Roman wall into Verulamium Park and past St Albans Cathedral to finish at St Albans Abbey Station.
Chipperfield and the Chess Valley, Chilterns
5.81 mi
+430 ft
-440 ft
3h 05
Moderate
Departure from Chipperfield (Hertfordshire)
A rewarding, scenic country walk exploring several commons and villages along with an attractive river valley. Good pubs!
Chalfont St Giles and Chiltern OAM
6.21 mi
+446 ft
-413 ft
3h 15
Moderate
Departure from Chalfont St Giles (Buckinghamshire)
A lovely walk that passes through woods and farmland with pleasant distant views. You can visit Chiltern Open Air Museum and Milton’s Cottage.
Note there is currently a temporary diversion in place (since May 2022) which prevents entry into Newlands Park whilst development work is undertaken. This description includes the diversion.
From Hemel Hempstead station
6.36 mi
+256 ft
-282 ft
3h 10
Moderate
Departure from Dacorum (Hertfordshire)
Starting from Hemel Hempstead Station this is a walk which can be enjoyed without a car. The station is right on the edge of the town so virtually all the route is through the open country, much of it through Boxmoor Trust land, on the plateau of the Chilterns and along the Grand Union Canal. There are lots of reminders of the history of the area from 1594 through WWII. If you are lucky you may see a couple of rare farm breeds kept on Trust land and some interesting birds along the canal.
Dancersend Wildlife Walk
5.03 mi
+502 ft
-505 ft
2h 45
Moderate
Departure from Halton (Buckinghamshire)
This walk is about the treats that await you in and around Dancersend Nature Reserve. In spring bluebells, primroses and cowslips, in summer many species of butterflies and the Chiltern gentian, in autumn fungi and the trees with their colourful display and winter where the birds are easier to spot.
Tring to Hastoe and back through Tring Park
4.30 mi
+387 ft
-384 ft
2h 20
Moderate
Departure from Tring (Hertfordshire)
Climb from the pretty market town of Tring to Hastoe and return through beautiful Tring Park a mix of mature woodland and parkland.
Tring Park and beyond, Tring Parish
6.52 mi
+440 ft
-423 ft
3h 25
Moderate
Departure from Tring (Hertfordshire)
A circular walk starting from Tring Town Centre and exploring the historic parkland.
Tringford, Little Tring, Tring Parish
3.15 mi
+102 ft
-98 ft
1h 30
Easy
Departure from Tring (Hertfordshire)
A circular walk starting from Tring Town Centre.
Stubbings Wood, Tring Parish
2.98 mi
+390 ft
-390 ft
1h 45
Easy
Departure from Tring (Hertfordshire)
A circular walk starting from Tring Town Centre and offering spectacular views.
Drayton Beauchamp, Tring Parish
4.57 mi
+217 ft
-220 ft
2h 15
Easy
Departure from Tring (Hertfordshire)
A circular walk starting from Tring Town Centre.
Tring Station, Wigginton and Tring Park, Tring Parish
4.77 mi
+325 ft
-325 ft
Duration unknown
Not specified
Departure from Tring (Hertfordshire)
A circular walk starting from Tring Town Centre.
Canals and Reservoirs, Tring Parish
5.43 mi
+85 ft
-79 ft
2h 35
Easy
Departure from Tring (Hertfordshire)
A circular wallk starting from Tring Town Centre.
Across the Tring Gap by Ridgeway and Chiltern Way
9.34 mi
+758 ft
-755 ft
4h 55
Moderate
Departure from Aldbury (Hertfordshire)
Experience the Ridgeway and Chiltern Way on a walk linking the woods of Ashridge with the woods above Tring Park across the Bulbourne Valley (Tring Gap).
Ivinghoe Beacon & Ashridge, Chilterns
8.71 mi
+902 ft
-902 ft
4h 50
Moderate
Departure from Aldbury (Hertfordshire)
This walk follows the ancient Ridgeway with stunning views from the tops of both Pitstone Hill and Ivinghoe Beacon, before returning through the beautiful woodland of the National Trust’s Ashridge Estate.
Tring Park Wild
Tourist office9.94 mi
+486 ft
-482 ft
5h 00
Moderate
Departure from Aldbury (Hertfordshire)
Enjoy scenic views, wooded valleys and ancient parkland on this 10km circular walk through the Chilterns. Starting in Tring, the walk takes in Dancersend nature reserve and the Ridgeway National Trail.
Tring Reservoirs Wild
6.72 mi
+102 ft
-98 ft
3h 10
Easy
Departure from Aldbury (Hertfordshire)
Stroll along the waterside and look for waterbirds on this gentle 13km walk. Starting at Tring railway station, it takes in College Lake nature reserve, a section of the Grand Union Canal and three reservoirs.
Forty Green and Penn
3.80 mi
+259 ft
-256 ft
2h 00
Moderate
Departure from Penn (Buckinghamshire)
An easy walk that climbs to the ridge on which Penn stands. Stroll through quiet woods and fields visiting the newly planted Jubilee Wood and the village of Penn with its ancient church and historic inns.
Aldbury to the Beacon and back through Ashridge
9.93 mi
+801 ft
-807 ft
5h 15
Moderate
Departure from Aldbury (Hertfordshire)
From picturesque Aldbury you follow the Ridgeway to Ivinghoe beacon, returning via the Ashridge boundary trail and the Chiltern Way. You can enjoy the contrasts between the two LDPs: airy ridges on the Ridgeway and the patchwork of woods and fields on the Chiltern Way.
Woodoaks Farm
4.83 mi
+377 ft
-381 ft
2h 35
Moderate
Departure from Three Rivers (Hertfordshire)
This short but varied walk starts from an historic farm, enjoys sweeping views and looks at some important local history. There's also the chance to explore nature in Philipshill and "No Dragon" woods.
You can finish the walk with some of the best cake in the area.
Gade Valley Nature Walk
3.91 mi
+466 ft
-466 ft
2h 10
Easy
Departure from Great Gaddesden (Hertfordshire)
Gordon Beningfield was an artist with an international reputation for his beautiful depictions of the natural world. He spent many happy hours walking through the countryside with his close friend, naturalist and broadcaster Dennis Furnell. This walk, one of their favourites, is described by Dennis.
Hertfordshire Mansions and Parklands - From Great Gaddesden
6.45 mi
+341 ft
-351 ft
3h 15
Moderate
Departure from Great Gaddesden (Hertfordshire)
This walk is over the undulating plateau of the Chiltern dip slope, through the parklands of some of the 18th Century mansions which dot the Chilterns. Although the land is now more given over to arable agriculture, the landscape is still greatly influenced by the great designers, including Capability Brown. A walk with great views over the Gade valley and a revelation of the life style of baronets and local squires in the 1700s and the lesser houses of their tenants.
From Great Gaddesden to Little Gaddessden
7.29 mi
+554 ft
-564 ft
3h 50
Moderate
Departure from Great Gaddesden (Hertfordshire)
This walk explores some of the hamlets of the Chilterns which, although close to Hemel Hempstead retain their remoteness in their quiet locations. It goes over the typical chalk uplands of the Gade valley and up to the beechwoods of the National Trust Ashridge estate. It passes charming 17th century cottages, a vineyard, a Buddhist Temple and long established churches. The country truly merits its AONB designation.
More walks in Chesham
Select a point of interest below:
Discover also walks in surrounding cities:
- Aldbury
- Amersham
- Ashley Green
- Aston Clinton
- Batchworth
- Beaconsfield
- Berkhamsted
- Bierton
- Bovingdon
- Broughton Hamlet
- Buckland
- Chalfont St Giles
- Chalfont St. Peter
- Chartridge
- Cheddington
- Chenies
- Chepping Wycombe
- Chesham Bois
- Chipperfield
- Cholesbury-cum-St Leonards
- Chorleywood
- Coleshill
- Cookham
- Croxley Green