Prestwood and Cobblershill Farm

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.

Details

86713485
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  • Walking
    Activity: Walking
  • ↔
    Distance: 8.23 km
  • ◔
    Average duration: 2h 45 
  • ▲
    Difficulty: Moderate

  • ⚐
    Back to start: Yes
  • ↗
    Ascent: + 139 m
  • ↘
    Descent: - 129 m

  • ▲
    Highest point: 226 m
  • ▼
    Lowest point: 141 m

Photos

Description of the walk

START & FINISH: High Street car park, (A) Prestwood HP16 9ER Grid ref: SP 872 008

(S/E) On leaving the car park turn right. Before Cross Roads Garage cross the road and turn left into Moat Lane.

(1) Walk along the pavement to the entrance on the right to Kimba Farm Stud and go down the concrete driveway. Go straight ahead between post and rail fences and then through a gate, eventually joining a track. Continue in the same direction for 250m to reach a footpath sign on the right heading into the woods. Take the path and descend through the woods. At the bottom of the woods, continue straight ahead with the field on the right and go past a house called Shercot to a road.

(2) Cross onto the grass verge and turn right for 100m and take the first left down a wide gravel drive to reach the entrance to Coney Hill. Bear left along the footpath and, at the top of the hill, the path leaves the wood into a beautiful meadow.

(3) Turn left along the field edge to shortly pass through a gate and continue for 100m to then re-enter the woods through a gate on the left. Follow the path to a T-junction by a 3-way finger post. Turn right onto the wide track, a byway, and stay on it for 500m ignoring all other paths.

(4) At a bridleway junction turn left, the path then bends round to the left before continuing ahead in the same direction. Continue on the main bridleway, ignoring footpaths on the left, to pass a house called Blossoms on the right. Keep going straight on and shortly come to a 5 way-junction. Continue straight across on a narrow bridleway that soon widens out into a track and then a lane that ends at Cobblers Hill Farm Cottage.

(5) Turn left and, after 20m, turn right to walk along the driveway past a pond on the left. Go through a gateway, passing a large barn on the left, and continue along a narrow path between fields and into a wood to shortly reach a path crossroads, with wooden fence gates on either side.

(6) Turn left through the wooden gate, and follow the footpath as it descends through the woods and eventually exits onto a quiet single-track lane. Turn right and follow the lane downhill to the end, to reach the junction with the main road, by Little Hampden Forge.

(7) Turn right and very quickly look for and take the signed footpath on the opposite side of the road, leading into the woods. A short distance in, take the left fork of two paths and a short distance later exit the wood by a metal kissing gate onto a glade. While crossing the glade, look right to enjoy the view up to Hampden House. Enter (B) Pepperboxes Wood and follow the main woodland path, passing a bench, as the path slowly climbs. Towards the top pass near a wooden fence on the left, and shortly after take a left path to reach a metal kissing gate to exit the woods. Pass across a small paddock and through a second kissing gate onto Greenlands Lane.

(8) Turn left on the lane and then immediately right onto a footpath past a five bar gate into Greenland Lane Allotments. Go to the right of a second five bar gate and continue on the right-hand edge, passing Kiln Common Orchard. The path exits in the far-right corner of the field, here turn right and at the end of John Hampden Way turn left.

(9) At the end of Mandeville Road, turn left and then right into Kiln Close. At the end of the Close head into the right-hand corner and take the path between two fences to a lane. Turn right and on joining the next road continue straight ahead towards Wye Country estate agents on the left and the Chequers Tree PH on the right. At the main junction turn left onto the High Street and follow for a short distance to return to the car park on the right.

(S/E)

"We hope you have enjoyed your walk. Please remember to rate the walk and add comments. We are interested in how we could improve the instructions or the route and would like to hear about any issues with paths on the walk."

Waypoints

  1. S/E : km 0 - alt. 197 m - High Street car park
  2. 1 : km 0.45 - alt. 197 m - Moat Lane
  3. 2 : km 1.82 - alt. 141 m - Right on road
  4. 3 : km 2.4 - alt. 164 m - Left along field edge
  5. 4 : km 3.35 - alt. 197 m - Bridleway left
  6. 5 : km 4.5 - alt. 226 m - Cobblershill Lane
  7. 6 : km 4.76 - alt. 211 m - Left through kissing gate
  8. 7 : km 6.09 - alt. 152 m - Road junction
  9. 8 : km 7.26 - alt. 205 m - Left on lane
  10. 9 : km 7.55 - alt. 203 m - Left on street
  11. S/E : km 8.23 - alt. 198 m - High Street car park

Notes

TERRAIN: Pleasant walking on good paths and quiet lanes. Two narrow paths, two significant climbs and several gates to pass through. No stiles.

START & FINISH: High Street Car Park, Prestwood HP16 9ER Grid ref: SP 872 008.

FOOD & DRINK: The Chequers Tree and Green Man pubs and various local convenience stores. None on route.

PARKING: High Street car park as above- free on Sundays.

LOCAL TRANSPORT: Bus 41 runs between High Wycombe and Great Missenden on Monday to Saturday. A few buses on Sunday

Worth a visit

(A) PRESTWOOD: The name has Anglo-Saxon origins and means priest-wood. This part of the Chilterns was famous for its cherry orchards and in the 19th century Londoners took day trips to see the spring blossom.

(B) PEPPERBOXES WOOD, also known as Lodge Wood, takes its name from the lodges at the bottom of The Glade, a long wide avenue leading to Hampden House. The Glade was reputedly cut in a single night to provide a view for Queen Elizabeth I when she visited the house.

Reviews and comments

4.3 / 5
Based on 1 review

Reliability of the description
5 / 5
Ease of following the route
4 / 5
Route interest
4 / 5
User 24605723

Overall rating : 4.3 / 5

Date of your route : Nov 16, 2025
Reliability of the description : ★★★★★ Very good
Ease of following the route : ★★★★☆ Good
Route interest : ★★★★☆ Good
Very busy route : No

Lovely gentle autumn walk, gentle slopes and mixture of landscapes. A little difficult to follow due to lots of leaf coverage on paths, particularly the section prior to joining Cobblers Hill Lane. There are some footpath cut through to avoid walking down Prestwood high street at the conclusion of the walk. Very quiet, only saw a couple walking together. Will return in the spring or earlier to complete in the opposite direction!

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