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Cholesbury-cum-St. Leonards walks

Organisation / Walking Club / Mountain guide
distance 6.22 km Vertical gain +63 m Vertical drop -55 m Duration 1h55 Easy Easy
Starting point Starting point in 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.

Organisation / Walking Club / Mountain guide
distance 9.32 km Vertical gain +109 m Vertical drop -104 m Duration 3h00 Moderate Moderate
Starting point Starting point in Cholesbury-cum-St. Leonards - 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.

Organisation / Walking Club / Mountain guide
distance 6.92 km Vertical gain +107 m Vertical drop -106 m Duration 2h15 Moderate Moderate
Starting point Starting point in 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.

Organisation / Walking Club / Mountain guide
Across the Chilterns: Chesham to Wendover
distance 16.80 km Vertical gain +225 m Vertical drop -205 m Duration 5h25 Moderate Moderate
Starting point Starting point in 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.

Organisation / Walking Club / Mountain guide
Dancersend Wildlife Walk
distance 8.09 km Vertical gain +144 m Vertical drop -147 m Duration 2h45 Moderate Moderate
Starting point Starting point in Halton (Buckinghamshire) - 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.

Organisation / Walking Club / Mountain guide
Berkhamsted to Frithsden with the Devil's Own
distance 10.09 km Vertical gain +123 m Vertical drop -131 m Duration 3h15 Moderate Moderate
Starting point Starting point in Berkhamsted - Hertfordshire

A walk through lovely Chiltern scenery with lots of interest on the way - a Norman Castle, WW1 trenches, a vineyard, canal and more.

Organisation / Walking Club / Mountain guide
Across the Tring Gap by Ridgeway and Chiltern Way
distance 15.04 km Vertical gain +205 m Vertical drop -204 m Duration 4h55 Moderate Moderate
Starting point Starting point in 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).

Organisation / Walking Club / Mountain guide
distance 14.02 km Vertical gain +258 m Vertical drop -258 m Duration 4h45 Moderate Moderate
Starting point Starting point in 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.

Tourist office
distance 16.00 km Vertical gain +146 m Vertical drop -145 m Duration 5h00 Moderate Moderate
Starting point Starting point in 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.

Tourist office
distance 10.81 km Vertical gain +30 m Vertical drop -31 m Duration 3h10 Easy Easy
Starting point Starting point in 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.

Walker
distance 8.50 km Vertical gain +174 m Vertical drop -148 m Duration 2h55 Easy Easy
Starting point Starting point in 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.

Organisation / Walking Club / Mountain guide
distance 28.48 km Vertical gain +388 m Vertical drop -403 m Duration 9h15 Difficult Difficult
Starting point Starting point in 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.

Organisation / Walking Club / Mountain guide
Aldbury to the Beacon and back through Ashridge
distance 15.98 km Vertical gain +234 m Vertical drop -235 m Duration 5h15 Moderate Moderate
Starting point Starting point in 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.

Walker
distance 11.34 km Vertical gain +140 m Vertical drop -142 m Duration 3h40 Moderate Moderate
Starting point Starting point in Wendover - Buckinghamshire

Circular walk from Wendover to the pub at Swan Bottom, across fields and through woods.

Organisation / Walking Club / Mountain guide
Wendover Woods and Cobblers Pits, Chilterns
distance 11.35 km Vertical gain +149 m Vertical drop -151 m Duration 3h40 Moderate Moderate
Starting point Starting point in 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.

Organisation / Walking Club / Mountain guide
Grims Ditch and Cobblers Pits, Chilterns
distance 15.82 km Vertical gain +240 m Vertical drop -242 m Duration 5h10 Moderate Moderate
Starting point Starting point in 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.

Organisation / Walking Club / Mountain guide
The Toughest Climb in the Chilterns
distance 13.51 km Vertical gain +407 m Vertical drop -404 m Duration 5h00 Easy Easy
Starting point Starting point in 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.

Organisation / Walking Club / Mountain guide
Ashridge and Little Gaddesden, Chilterns
distance 11.90 km Vertical gain +81 m Vertical drop -79 m Duration 3h40 Moderate Moderate
Starting point Starting point in Aldbury - Hertfordshire

Visit some of the quieter parts of the Ashridge Estate on the way to Hudnall Common and Little Gaddesden.

Organisation / Walking Club / Mountain guide
distance 8.32 km Vertical gain +53 m Vertical drop -52 m Duration 2h30 Moderate Moderate
Starting point Starting point in 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.

Walker
distance 18.18 km Vertical gain +243 m Vertical drop -247 m Duration 5h55 Moderate Moderate
Starting point Starting point in 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.

Organisation / Walking Club / Mountain guide
Marsworth Canals and Reservoirs
distance 7.61 km Vertical gain +23 m Vertical drop -23 m Duration 2h15 Easy Easy
Starting point Starting point in 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.

Walker
distance 13.02 km Vertical gain +126 m Vertical drop -89 m Duration 4h05 Easy Easy
Starting point Starting point in 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.

Walker
Holmer Green to Coleshill via Penn Wood
distance 11.07 km Vertical gain +42 m Vertical drop -50 m Duration 3h15 Moderate Moderate
Starting point Starting point in 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.

Organisation / Walking Club / Mountain guide
distance 9.32 km Vertical gain +102 m Vertical drop -103 m Duration 2h55 Moderate Moderate
Starting point Starting point in 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.

Walker
River Chess highlights : Chalfont & Latimer, Chiltern AONB
distance 9.10 km Vertical gain +68 m Vertical drop -68 m Duration 2h50 Easy Easy
Starting point Starting point in 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.

Organisation / Walking Club / Mountain guide
distance 9.25 km Vertical gain +71 m Vertical drop -71 m Duration 2h50 Easy Easy
Starting point Starting point in Penn - Buckinghamshire

An undulating walk through woodland and arable farmland, via Penn House Estate, Common Wood and Penn Wood.

Walker
distance 18.93 km Vertical gain +229 m Vertical drop -265 m Duration 6h05 Moderate Moderate
Starting point Starting point in 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.

Walker
distance 10.77 km Vertical gain +64 m Vertical drop -60 m Duration 3h15 Easy Easy
Starting point Starting point in 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.

Organisation / Walking Club / Mountain guide
distance 9.58 km Vertical gain +104 m Vertical drop -111 m Duration 3h00 Moderate Moderate
Starting point Starting point in Chenies - Buckinghamshire

This 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.

Organisation / Walking Club / Mountain guide
distance 18.23 km Vertical gain +208 m Vertical drop -297 m Duration 5h50 Moderate Moderate
Starting point Starting point in 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.

Walker
Hughenen Manor - West Wycombe, Dashwood Mausoleum, Hellfire Caves
distance 9.78 km Vertical gain +252 m Vertical drop -246 m Duration 3h30 Moderate Moderate
Starting point Starting point in Hughenden - Buckinghamshire

A circular loop offering heaps of views, wildlife spotting, and history preserved by the National Trust. This walk goes up and down the 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.