The Chillerton Challange
Starting and finishing at the Chequers Inn, this walk will take you through the Wilderness over Ramsdown and into Chillerton. It continues towards New Barn Farm and over Chillerton Down with panoramic views of the Island. Then a return via Roslin and Cridmore.
Technical sheet
Creation:
Last update:
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Activity: Walking
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Distance: 13.07 km
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Average duration: 4h 25
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Difficulty: Not specified
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Return to departure point: Yes
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Vertical gain: + 241 m
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Vertical drop: - 243 m
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Highest point: 164 m
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Lowest point: 31 m
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Country: United Kingdom
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District: Rookley
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Start/End: N 50.64455° / W 1.278848°
Waypoints
- S/E : km 0 - alt. 62 m
- 1 : km 0.02 - alt. 61 m - Cross the road and follow the lane to Rookley Farm House - Farm Lane
- 2 : km 0.81 - alt. 38 m - Turn left. Walk towards the stile - Rookley Farm House
- 3 : km 1.03 - alt. 31 m - Cross the River Median via a footbridge and a stile - Footbridge, stile and ford
- 4 : km 1.22 - alt. 34 m - Go through the gate and carry on up the lane - Gateway
- 5 : km 1.47 - alt. 40 m - Turn right onto Cridmore Lane - Cridmore Lane
- 6 : km 1.61 - alt. 51 m - Turn left onto Loverstone Lane - Loverstone Lane
- 7 : km 1.91 - alt. 52 m - Directly after Lower Rill Cottages turn right up a concrete drive - Lower Rill Cottages
- 8 : km 1.94 - alt. 54 m - Go through a gate into a copse - Gate
- 9 : km 2.01 - alt. 61 m - Go through a second gate and cross the field - Gate
- 10 : km 2.09 - alt. 70 m - Junction with G21. Continue through the trees. - Junction
- 11 : km 2.28 - alt. 87 m - Turn right and climb the hill - Gate and hill!
- 12 : km 2.37 - alt. 109 m - At the top of the hill, go through a gate and turn left (G15) - Top of hill
- 13 : km 2.78 - alt. 117 m - At the junction, turn right onto G15 (Hollow Lane) - Junction
- 14 : km 3.6 - alt. 49 m - Follow Hollow Lane until the main road and turn left. Follow the road - carefully. - Main Road
- 15 : km 3.74 - alt. 52 m - Turn right onto G6 (Garn Lane) - Garn Lane
- 16 : km 4.93 - alt. 70 m - Follow Garn Lane until the junction with G8. Turn left and continue on G6. - Junction
- 17 : km 5.3 - alt. 54 m - Junction with New Barn Lane. Carry on towards New Barn Farm (G7) - Junction
- 18 : km 5.49 - alt. 68 m - Pass New Barn Farm, turn left and walk up the lane - Turn left
- 19 : km 5.93 - alt. 131 m - Continue up the field and turn right towards a gate - Turn right
- 20 : km 5.97 - alt. 138 m - Do not go through the gate. Turn left onto the G22 and follow the path - Turn left
- 21 : km 6.21 - alt. 160 m - Pass a concrete pond. Carry straight on - Concrete pond
- 22 : km 6.33 - alt. 160 m - Pass through a gate and through some trees - Gate
- 23 : km 6.36 - alt. 158 m - Turn left onto N146 - Join N146
- 24 : km 6.96 - alt. 161 m - Continue towards the tv mast - Contine
- 25 : km 7.97 - alt. 159 m - Pass the tv mast. Go through a gate, cross a concrete road and then go through another gate - Gates and road
- 26 : km 8.42 - alt. 117 m - Junction with G12b and G12a. Go through the gate on to G12 - Gate
- 27 : km 8.62 - alt. 113 m - Bear slightly left at the junction with G13. Carry on down the path - Junction
- 28 : km 9.08 - alt. 91 m - Turn right on to Berry Shute. Be very careful! - Berry Shute
- 29 : km 9.27 - alt. 102 m - Carefully cross the road into Berry Lane - Berry Lane
- 30 : km 9.78 - alt. 96 m - Pass Ramsdown Farm and continue towards Roslin - Ramsdown Farm
- 31 : km 10.21 - alt. 68 m - At the junction with Loverstone Lane bear slightly right towards Roslin - Junction with Loverston Lane
- 32 : km 10.37 - alt. 57 m - Turn left after first barn. - Roslin Farm
- 33 : km 10.48 - alt. 57 m - Carry on into the field. Follow the path (Sandy Lane) keeping the hedge on your left - Sandy Lane
- 34 : km 10.82 - alt. 49 m - Turn right at the corner of the field. This is the junction with G16 - Turn right
- 35 : km 11.05 - alt. 45 m - Join the lane, pass Little Cridmore Cottages and turn left - Cridmore
- 36 : km 11.21 - alt. 46 m - Pass Cridmore Farm and carry straight on towards the farm lane (G24) - Cridmore Farm
- 37 : km 11.5 - alt. 40 m - The path enters an open field carry straight on. Keep the fence on your right - Open field
- 38 : km 11.64 - alt. 38 m - Turn right after the gate and stile - Gateway and stile
- 39 : km 11.94 - alt. 35 m - Follow the hedge on your left then cross the field towards the stile - Cross the field
- 40 : km 12.02 - alt. 34 m - Cross the River Medina on a footbridge - Stile, footbridge and ford
- 41 : km 12.32 - alt. 40 m - Go through a gate at the junction with GL11 - Gate
- 42 : km 12.5 - alt. 48 m - Continue on Appleford Farm Lane - Farm lane
- 43 : km 12.76 - alt. 58 m - Turn left on to Niton Road - Niton Road
- 44 : km 13.01 - alt. 62 m - Return to the Chequers Inn. Cheers! - Return to the Chequers
- S/E : km 13.07 - alt. 62 m
Other walks in the area
The Chillerton Challange
This recommended walk of about 9 miles will take you over the river Medina, up and over Ramsdown to Chillerton village. Then north to Gatcombe to start the climb onto Newbarn Down and Chillerton Down with panoramic views across the island. Passing close to the TV mast you descend through the old marl pits and return via the water meadows of the wilderness.
The wilderness walkabout
Mostly on bridleways with some long but gentle gradients.
The Chequers Circular
Great walk around the Chequers Inn where you can stop for refreshment after the effort.
Birchmore Experience

Walk from Rookley Post office back to Rookley Main Road via Birchmore Lane. The Walk on the map actually starts and returns to Oakdene.
Around Arreton
A walk across farmland and by historic Haseley Manor, one of the oldest houses on the Island.
From the White Horse
A great pub walk from the White Horse in Whitwell.
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