Refine your search for walks in Penn
A Penn Circuit, Chilterns
An undulating walk through woodland and arable farmland, via Penn House Estate, Common Wood and Penn Wood.
Holmer Green to Coleshill via Penn Wood
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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.
Old Amersham to Chipperfield
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.
Hughenen Manor to West Wycombe, Dashwood Mausoleum, Hellfire Caves
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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.
Chalfont St Giles and Chiltern OAM
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.
Bourne End Circular via Thames Path
On the off chance that you are searching for a picturesque and refreshing walk by the water, this is for you. From overlooking the River Thames from the top of a hill to strolling along the Thames path, this is ideal for a sunny weekend walk.
Bourne End and Cookham Dean Circular
From the water meadows of Cock Marsh to the well-known viewpoint on Winter Hill, passing through the picturesque village of Cookham Dean, this is an invigorating circular walk with excellent views. Some of the hills are steep, but the paths are good and there are no stiles.
Bourne End to Marlow, around Reading
An energetic walk with splendid views, through a picturesque village and ancient woodland.
Bourne End to Maidenhead via the Thames Path, around Reading
Follow the Thames Path through the lovely scenery of Cliveden Reach. Visit Boulter's lock, enjoy the wildlife on the newly-created Jubilee River and pass close to Eton College.
Bourne End to West Wycombe
First 2 miles are flat, along the Thames Path & Spade Oak Nature Reserve to Little Marlow. The rest of the stage is tough and very hilly with many steep climbs and mostly off-road thru'the Chiltern Hills. The route goes up around the back of High Wycombe to finish just past the National Trust owned village of West Wycombe at Pedestal Roundabout at junction of A40 and A4010.
Prestwood Route, Chilterns
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.
River Chess highlights : Chalfont & Latimer, Chiltern AONB
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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.
Naphill Route, Chilterns
A scenic walk around Naphill. Full of interest: there is a fascinating history of WWII codebreaking and you pass the home of a famous sculptor and a music camp.
Sarratt Bottom and Chenies from Little Chalfont
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.
Chalfont and Latimer to Chorleywood via Flaunden
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.
Across the Chilterns: Chesham to Wendover
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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.
Stanley Spencer's Cookham
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Sir Stanley Spencer was one of the most important painters of the 20th century. This walk will take you round his home village, a place he regarded as ‘heaven on earth’. It also ventures out into the surrounding countryside and alongside the Thames.
The locations of several of his paintings are highlighted in the description with more details in the "to do or see" section.
Burnham Beeches, Chilterns
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Scenic Burnham Beeches National Nature Reserve is owned by the City of London. They describe it as one of Europeʼs most important places for wildlife. Burnham Beeches is particularly colourful in spring and autumn, but well worth a visit at any time of year.
Cookham Circular
A mostly level walk on good paths, much of it on the Green Way. No stiles. Refreshment is available in picturesque Cookham village, once home to the artist Stanley Spencer. The village dates back to prehistoric times and has many fine old buildings.
Ballinger and The Lee
A mixed route on footpaths and tracks through fields and woodland, visiting the picturesque village green at The Lee.
Marlow to Henley, around Reading
A mainly level walk along the scenic Thames Path then rising to overlook the famous regatta course before descending to the much-photographed river bridge and church in Henley-on-Thames.
Marlow Circular via Spade Oak Nature Reserve
A level walk on good paths apart from steep steps to bridge across the A404. There are three pubs en route. A wide variety of waterfowl may be seen in the Spade Oak Nature Reserve and on the River Thames.
Marlow to Windsor, Thames Valley
This walk follows the Thames Path to Windsor with a detour along the Eton College Olympic Rowing Lake. You will find boating on the Thames, an ancient wetlands area, an historic village with artistic connections, beautiful Clivedon, Reach and Boulter's lock, the famous railway bridge, Monkey Island, Eton's impressive rowing lake, arboretum and the nature reserve Windsor Castle.
Marlow Circular, Chilterns
A walk along the Thames Path to Temple Lock and through the picturesque Harleyford Estate to the woods of Marlow Common and the new Chiltern Society Local Nature Reserve.
Hampden Monument Route
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This walk takes you through beautiful rolling countryside, past the home of an English Civil War hero and the monument erected in his memory.
More walks in Penn
Select a point of interest below:
Discover also walks in surrounding cities:
- Latimer and Ley Hill
- Little Chalfont
- Little Marlow
- Little Missenden
- Marlow
- Marlow Bottom
- Medmenham
- Nettleden with Potten End
- Northchurch
- Piddington and Wheeler End
- Princes Risborough
- Seer Green
- Shottesbrooke
- Stoke Poges
- Taplow
- The Lee
- Wendover
- West Wycombe
- Wexham
- Wexham Court
- White Waltham
- Wigginton
- Wooburn