|35 km/21 mi Circular||677m//2221ft||Difficult|
Like all my routes, they are best followed using:
1. Ventnor Downs to Freemantle Gate
2. Freemantle Gate to St. Catherine's Hill
Continue onwards keeping Freemantle gate on your left. At the Deer Gates, go through the gate and keep to the narrow track till it opens up into a large field.
Keep close to the hedge until you reach metal gate. After the gate turn right, and descend till you reach the main road.
At the road, take a left, then a right, just before the houses on to the NT96 to Southford.
After the old railway embankment turn left and almost immediately right and continue straight on to the farm houses in the near distance. After you exit Ford Farm Lane, turn right on the main road for 185 metres, and then turn left on to the NT89 St. Catherine's Hill.
After one kilometre take the non-signposted bridleway on your right. Take this bridleway, continuing steeply uphill till reach the top of St. Catherine’s Hill. Ensure you keep to the left of the house near the top. You should now be seeing the Hoy Monument.
3. St. Catherine's Hill to Chequers Inn
Head for the monument, and go through the wooden gate at the left (west side) of the Monument. The rights-of-way are somewhat confused here, and don’t match the map exactly - so take care.
Head right and downhill till you reach a T-junction/fence. Care is required here. Take the GL60, on our left. Continue downhill, and through the small wood, where you take a right at the edge of the wood, to stay on the GL60. Continue downhill through the farm until you reach the main road.
At the main road, turn right until you reach the Byway C32A Take the Byway past the sewage farm until you reach the road 1.5 kilometres later.
Go straight over the crossroads, heading for Shorwell/Brighstone. After 330 metres, turn left on the SW56Byway. After one kilometre, turn right to head uphill, and around Bucks Farm until you reach the main road.
At the main road take a right for 200 metres, then a left on to the SW43 to Billingham.
At the road turn left, and after 150 metres take the SW44 on the right,. After 120 metres turn left on the unmarked bridleway. Continue uphill towards the road
At the road turn right, and keep left at the next junction. After going past a couple of cottages, take the next right at the junction. After a 100 metres turn left on to the G18to Rookley.
Cross the stream, and continue on the Bridleway past the farm until you reach the road at the Chequers Inn.
4. Chequers Inn to Freemantle Gate
Go straight over the junction and join the Chequers Inn Road.
At the next road junction go straight ahead to join the GL18Bto Main Road.
At the Main Road, turn left, and after 350 metres, take a right at the RSPCA sign. After 350 metres join the Bridleway on your right GL22 till you exit by the old greenhouses.
After the Greenhouses turn right to follow the well marked Squirrel Trail all the way back to Wroxall.
The Squirrel Trail is well signposted. You will go through Freemantle Gate, which you passed by earlier.
5. Freeemantle Gate to Ventnor Downs
After Freemantle Gate, use the Bridleway on your left. At the junction at the top of Appuldurcombe Road follow the Squirrel Trail sign, for the last time.
Continue through the Village past the Spar Shop until the road forks by the Four Seasons Inn. Take the left fork on to Manor Road, and then the next left on to Stenbury View as the road bears right, take the bridleway V15 to Wroxall Down & Ventnor.
Continue on this bridleway uphill, then follow the V4 Wroxall Down, back to your start point.
Starting at the highest point on the Island, the route follows the chalk ridge to the outskirts of Wroxall.
From Wroxall, you make your way to the outskirts of Godshill, crossing the River Yar. You then climb most of the way up Stenbury Down, then drop down to cross the River Medina. From the river valley you climb up St. Catherine's Down.
You then return to Godshill via lonely farm tracks and short climbs. At Godshill you return to Wroxall where you make your final pull up to our start point.
- Ordnance Survey Map
- 1:25000 - Explorer OL29 - Isle of Wight
- 1:50000 - Landranger 196 - The Solent & Isle of Wight
Sat Nav: PO38 1AH
OSGB: SZ 562 784
There are no viable escape routes.