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Penn walks
Forty Green and Penn
Association / Club / Walk leader
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.
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.
Holmer Green to Coleshill via Penn Wood
Visorando Member
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.
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.
High Wycombe to Chequers
8.71 mi
+732 ft
-351 ft
4h 40
Moderate
Departure from Buckinghamshire
The third stage leaves High Wycombe, passes Hughenden Manor estate of former Prime Minister Benjamin Disraeli, then continues through Chiltern hills and woodlands past Hampden House seat of John Hampden prominent parliamentarian in the Civil War, joining the Ridgeway national trail on the edge of the Chequers estate.
At this point, continue on stage four to Little Kimble station.Alternatively, follow the Ridgeway eastward to Wendover station for services to Amersham Underground station on the Metropolitan Line.
River Wye: a circuit from High Wycombe
5.45 mi
+72 ft
-69 ft
2h 35
Easy
Departure from Buckinghamshire
A short walk from High Wycombe based around the river Wye. Learn about the history of the river, see the work of the "Revive the Wye Partnership" and the place where the Chiltern Society started in 1965.
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.
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.
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.
Bourne End Circular via Thames Path
7.19 mi
+167 ft
-177 ft
3h 25
Moderate
Departure from Wooburn (Buckinghamshire)
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
5.01 mi
+282 ft
-272 ft
2h 35
Easy
Departure from Wooburn (Buckinghamshire)
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
5.28 mi
+430 ft
-440 ft
2h 50
Easy
Departure from Wooburn (Buckinghamshire)
An energetic walk with splendid views, through a picturesque village and ancient woodland.
Bourne End to Maidenhead via the Thames Path, around Reading
5.57 mi
+26 ft
-23 ft
2h 35
Easy
Departure from Wooburn (Buckinghamshire)
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 High Wycombe
5.52 mi
+420 ft
-292 ft
2h 55
Moderate
Departure from Wooburn (Buckinghamshire)
The second stage continues on the Thames Path from Bourne End for a short distance, then climbs up through the Chiltern woodlands to descend into High Wycombe.
At this point, continue on stage three to Chequers.Alternatively, there are regular bus services back to Bourne End (36/37) or Windsor (37/104). You can also take the Chiltern Railways train to London, Oxford or Birmingham.
Bourne End to West Wycombe
10.70 mi
+1,083 ft
-879 ft
5h 50
Moderate
Departure from Wooburn (Buckinghamshire)
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
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.
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.
Naphill Route, Chilterns
7.14 mi
+814 ft
-817 ft
4h 00
Moderate
Departure from Hughenden (Buckinghamshire)
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
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.
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.
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.
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.
Stanley Spencer's Cookham
3.76 mi
+56 ft
-56 ft
1h 45
Easy
Departure from Cookham (Royal Borough of Windsor and Maidenhead)
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
5.62 mi
+171 ft
-164 ft
2h 45
Easy
Departure from Burnham (Buckinghamshire)
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
4.45 mi
+33 ft
-39 ft
2h 05
Easy
Departure from Cookham (Royal Borough of Windsor and Maidenhead)
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
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.
Marlow to Henley, around Reading
8.61 mi
+102 ft
-89 ft
4h 05
Moderate
Departure from Marlow (Buckinghamshire)
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
5.57 mi
+23 ft
-26 ft
2h 35
Easy
Departure from Marlow (Buckinghamshire)
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 Henley
9.93 mi
+69 ft
-72 ft
4h 35
Moderate
Departure from Marlow (Buckinghamshire)
This is the ninth stage of the multi-day route "Railways and Waterways, between Oxford and London".
After a diversion, the walk joins the River Thames at peaceful Hurley Lock, then meanders through water meadows and a deer park, passes a popular traditional pub and Hambleden Lock before following the course of the world-famous Henley Regatta into the town.
Marlow to Windsor, Thames Valley
14.07 mi
+30 ft
-52 ft
6h 30
Moderate
Departure from Marlow (Buckinghamshire)
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
6.35 mi
+256 ft
-246 ft
3h 10
Easy
Departure from Marlow (Buckinghamshire)
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.
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.
Hampden Monument Route
5.04 mi
+446 ft
-446 ft
2h 40
Moderate
Departure from Great and Little Hampden (Buckinghamshire)
This walk takes you through beautiful rolling countryside, past the home of an English Civil War hero and the monument erected in his memory.
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.
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.
Black Park Family Circular
3.19 mi
+59 ft
-66 ft
1h 30
Easy
Departure from Wexham (Buckinghamshire)
Black Park is a great place for a family outing. This short walk passes through lovely woodland and open heathland. You will also pass Pinewood Studios. Leave enough time to relax at the café or have a picnic by the lake.
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