Refine your search for walks in Cholesbury-cum-St Leonards
Cholesbury-cum-St Leonards walks
Cholesbury Camp, Chilterns
Association / Club / Walk leader
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.
Chiltern 60k bike ride
Visorando Member39.28 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.
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.
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.
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.
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 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 Chilterns: Chesham to Wendover
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.
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.
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.
Wendover to The Plough at Cadsden
5.28 mi
+568 ft
-479 ft
2h 55
Easy
Departure from Wendover (Buckinghamshire)
This section of the walk takes you from Wendover down to Buckmoor End (where there is a pit stop and possibly a bacon sarnie!) across in front of Chequers through the nature reserve and over to The Plough at Cadsden.
Wendover to Watlington, The Ridgeway the Other Way
17.69 mi
+1,260 ft
-1,306 ft
9h 15
Difficult
Departure from Wendover (Buckinghamshire)
The Ridgeway the other way. The National Trail from NE to SW. This Stage 2 is the most undulating with several climbs in and out of valleys and is, therefore, the most strenuous part of The Ridgeway. The route climbs Coombe Hill, passes by Pulpit Hill fort and over Lodge Hill. Goes around Bledlow Great Wood near Chinnor to go along a disused railway and go underneath the M40. It goes along the bottom edge of the Chilterns scarp and passes Watlington Hill.
Wendover to Old Swan Pub
7.05 mi
+535 ft
-548 ft
3h 40
Moderate
Departure from Wendover (Buckinghamshire)
Circular walk from Wendover to the pub at Swan Bottom, across fields and through woods.
Grims Ditch and Cobblers Pits, Chilterns
9.83 mi
+791 ft
-797 ft
5h 15
Moderate
Departure from Wendover (Buckinghamshire)
A varied walk taking in lovely woods, a hillfort, beautiful views over Aylesbury Vale and the peaceful Wendover Arm of the Grand Union Canal.
Wendover Woods and Cobblers Pits, Chilterns
7.05 mi
+518 ft
-525 ft
3h 40
Moderate
Departure from Wendover (Buckinghamshire)
A varied walk climbing to a hillfort in Wendover woods with beautiful views over Aylesbury Vale. Return by the peaceful Wendover Arm of the Grand Union Canal.
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.
The Toughest Climb in the Chilterns
8.63 mi
+1,437 ft
-1,434 ft
5h 15
Difficult
Departure from Wendover (Buckinghamshire)
A 130m climb up the north face of Coombe Hill is as tough as it gets round here. Starting in Wendover you visit several quieter summits before the big one and are rewarded for your efforts by lovely, varied scenery and great views.
The Chiltern Link
8.41 mi
+472 ft
-548 ft
4h 15
Easy
Departure from Wendover (Buckinghamshire)
Follow an ancient trade route from Wendover to Chesham through open fields, lovely beech woodland and the peace and quiet of classic Chilterns countryside. Thanks to the Chiltern Society’s Donate-a-Gate scheme you can enjoy your walk without the need to clamber over stiles.
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.
Ashridge and Little Gaddesden, Chilterns
7.33 mi
+256 ft
-256 ft
3h 35
Moderate
Departure from Aldbury (Hertfordshire)
Visit some of the quieter parts of the Ashridge Estate on the way to Hudnall Common and Little Gaddesden.
Ashridge Bluebell Walk, Chilterns AONB
5.55 mi
+253 ft
-253 ft
2h 45
Moderate
Departure from Aldbury (Hertfordshire)
The National Trust Estate at Ashridge is one of the best places in the country to see bluebells in spring. This gentle walk will take you through carpets of this beautiful plant, and also looks at the history of the estate. There are wonderful views over the valley from Duncombe Terrace.
It’s a lovely walk at any time of year but can be very muddy in Winter so wear suitable footwear!
The Chilterns above Tring
11.30 mi
+778 ft
-784 ft
5h 50
Moderate
Departure from Aldbury (Hertfordshire)
National Trails and Long Distance Paths crisscross the Chilterns in this area. This Circular Walk makes use of short stretches of at least five such to provide a beautiful and varied walk through Chiltern woodland, on Chiltern chalk downs with wide vistas from the scarp edge of the hills, along a stretch of the historic Grand Union Canal, and through one of the prettiest villages in Hertfordshire.
Ridgeway Loops from Ashridge
9.98 mi
+1,040 ft
-1,024 ft
5h 30
Moderate
Departure from Aldbury (Hertfordshire)
A circular trail near Berkhamstead covering the Ridgeway, Grim's ditch, Pitstone Hill, Steps Hill, Ivinghoe Beacon, Beacon Hilll, Icknield Way trail. Starting at Ashridge monument where there is national trust parking.
Marsworth Canals and Reservoirs
4.73 mi
+75 ft
-79 ft
2h 15
Easy
Departure from Marsworth (Buckinghamshire)
This walk is good for both ‘Arms’ and legs. Not only that, what better way to get some fresh air into your lungs than to explore the waterways near Tring? The route includes a visit to one of the best birdwatching sites in the area, Wilstone Reservoir.
Little Hampden, Dunsmore and Coombe Hill
5.29 mi
+440 ft
-440 ft
2h 50
Moderate
Departure from Great and Little Hampden (Buckinghamshire)
A beautiful ridge walk through Chiltern woodlands with some magnificent views as you pass over Coombe Hill.
Prestwood and Cobblershill Farm
5.14 mi
+453 ft
-423 ft
2h 45
Moderate
Departure from Great Missenden (Buckinghamshire)
The walk quickly leaves Prestwood and uses some of the less frequented paths to enjoy the beautiful countryside in the surrounding area. The route includes beautiful meadow views, woodland walking, and crosses the stunning glade to Hampden House.
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.
26km run from Amersham Station
16.38 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.
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.
Ivinghoe and Pitstone Hill
4.31 mi
+308 ft
-318 ft
2h 15
Moderate
Departure from Ivinghoe (Buckinghamshire)
A walk suitable for everyone. You start by climbing steadily until you are on top of Pitstone Hill from where you will have stunning views over the Vale of Aylesbury, the Ivinghoe Hills and the woods of Ashridge. On the way back to Ivinghoe you pass close to Pitstone Windmill.
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.
Prestwood Route, Chilterns
5.79 mi
+325 ft
-328 ft
2h 55
Moderate
Departure from Hughenden (Buckinghamshire)
A wonderful opportunity to combine a stroll round Prestwood Nature Reserve with a lovely walk in the surrounding area. At Peterley Manor Farm there is the opportunity to do a little ‘pick your own’ for such delights as strawberries, gooseberries, raspberries and various vegetables.
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.
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.
Ivinghoe Beacon to Wendover, The Ridgeway the Other Way
11.33 mi
+712 ft
-1,027 ft
5h 50
Moderate
Departure from Ivinghoe (Buckinghamshire)
The Ridgeway the other way. The NationalTrail from NE to SW. This Stage 1 goes over the Chilterns, across the Grand Union Canal, past Tring, through the Three Hundreds of Aylesbury to reach the market town of Wendover.
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.
Hughenen Manor to West Wycombe, Dashwood Mausoleum, Hellfire Caves
6.08 mi
+741 ft
-735 ft
3h 25
Moderate
Departure from Hughenden (Buckinghamshire)
This circular offers heaps of views, wildlife spotting, and history preserved by the National Trust. It goes up and down the Chilterns hills and woodlands where end of May-June you can enjoy the bluebells. Keep your ears and eyes wide open listening to the whistling red kites or spot some pheasant or squirrels.
More walks in Cholesbury-cum-St Leonards
Discover also walks in surrounding cities:
- Aldbury
- Amersham
- Ashley Green
- Aston Abbotts
- Aston Clinton
- Aylesbury
- Beaconsfield
- Berkhamsted
- Bierton
- Bovingdon
- Bradenham
- Broughton Hamlet
- Buckingham Park
- Buckland
- Caddington
- Chalfont St Giles
- Chalfont St. Peter
- Chartridge
- Cheddington
- Chenies
- Chepping Wycombe
- Chesham
- Chesham Bois
- Chipperfield
- Chorleywood
- Coleshill
- Creslow
- Cublington
- Dacorum
- Downley
- Drayton Beauchamp
- Dunstable
- Eaton Bray
- Edlesborough
- Ellesborough
- Flaunden
- Great and Little Hampden
- Great and Little Kimble cum Marsh
- Great Billington
- Great Gaddesden
- Great Missenden
- Halton
- Hazlemere
- Hughenden
- Hulcott
- Ivinghoe
- Kensworth
- Kingsbrook
- Lacey Green
- Latimer and Ley Hill
- Little Chalfont
- Little Gaddesden
- Little Missenden
- Markyate
- Marsworth
- Mentmore
- Nettleden with Potten End
- Northchurch
- Penn
- Pitstone
- Princes Risborough
- Sarratt
- Seer Green
- Slapton
- Stoke Mandeville
- Studham
- The Lee
- Totternhoe
- Tring
- Tring Rural
- Watermead
- Weedon
- Wendover
- West Wycombe
- Weston Turville
- Whipsnade
- Wigginton
- Wing
- Wingrave with Rowsham