From the car park, cross the road and go up the steps and through the kissing gate to follow the clear path which first goes diagonally left then straight up the hill towards the Oratory, passing the Chale Bay Mackerel seat on the way to a kissing gate on the skyline. Go through it, but immediately turn left and away from the Oratory, which we visit at the end of the trail. Follow the grassy track leading gently downhill towards Chale and the sea, following the line of the hedge on the left. Soon the path bends right, soon meeting up with the fence again and this leads into an area with a small ridge on the left and old chalk quarries on the right. Follow a line through the valley between them and eventually reach an open area. Go straight across and pass through the gate straight ahead marked by a fingerpost onto St Catherine’s Down. Follow the wide, grassy path to the Hoy Monument.
Turn left and go through the gate in the fence by the plinth. Turn immediately right and downhill, then right at the T-junction signed C3. After 45yds (40m) turn right, and go through two more gates. Take a straight line across the field aiming for the right-most gate in the boundary, leading onto a road. On a clear day you can see Culver Down to the east and Tennyson Down to the west: the full extent of the Island.
Turn right at the road, then left onto the path GL26 by the wall of The Hermitage. Follow the path round the copse until it reaches a track by a house. Turn left through a metal gate taking path NT78 and then through another metal gate and down a hill until you reach a junction. Turn left for 30yds (25m), then right through a gate. Keep the fence to your left and follow the path, continuing across a field on the track heading down the valley.
50yds (45m) before the field gate leading into a farm/wood yard, take the right-hand path which crosses through the hedge by a footbridge and gate. Keeping the fence to your left, continue on the path bending above Wydcombe House. Go through the gate and down to the track. Turn left and follow the track bending left. At the junction by the stream, turn sharp right to skirt Wydcombe House. Bear right by the ornamental stone arch and after 20yds (20m) follow the path straight ahead for 15yds (15m). Then take the path which bends diagonally right down to the banks of a stream. Go over the footbridge and follow the stony tree-lined track straight ahead. When the path leaves the valley it emerges into a field by a stile. Cross through the gap in the hedges about 20yds (20m) in front, and cross the field to the top right-hand corner and a pair of stiles hidden behind gorse bushes. Cross the stile on the right and turn right after 5yds (5m) to join the diagonal path climbing onto Head Down.
Cross the stile at the top of the slope by the National Trust sign for Wycombe and turn left to reach another stile 20yds (20m) away. Turn right onto a level green track and pass through a gate onto the hillside. The path goes diagonally left towards the radio mast on the skyline, passing between two small mounds before climbing steeply and zig-zagging to the left of an old quarry area. Go through the gate then head straight uphill towards St Catherine’s Oratory. Look at the unfinished 18th-century lighthouse base at the base of the radio mast, then go through the kissing gate by the trig point to the Oratory. Head downhill to pass through a kissing gate and follow the outward route back to Blackgang Chine car park.
Getting To: Blackgang viewpoint car park (grid ref SZ490767)
By car: Blackgang Viewpoint car park is off of the A3055 in the far south of the Island, just up the road from Blackgang Chine. Nearest postcode PO38 2JB
By foot: Blackgang Viewpoint car park is on the Isle of Wight coastal path.
By bus: Southern Vectis bus no 6 from Newport to Ventnor passes along the A3055. Alight at the Viewpoint car park.
By bike: Sustrans regional ‘Round the Island’ route 67 passes along the A3055 and Blackgang Viewpoint car park.
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