The weather looked ominous when I got dropped off at Ferrybridge and set off along the A354 into the wind and under dark skies.
First impressions weren't very good as a lot of Chiswell seemed to be boarded up.
I also naively thought that I would be walking around the island at low level but was soon climbing steeply up and around the first of many quarries.
A diversion took me into Tout Quarry that has been changed into a sculpture park with over fifty works by leading artists including Antony Gormley.
Chiswell and the road to the mainland
One of the rock sculptures depicting the old quarrying methods
The views were probably spectacular on a clear day but all that could be seen were the white horses in the sea far below.
The view inland was pretty forgettable and Weston was perhaps the ugliest town I have ever seen and Southwell business park was bleak concrete covered in barbed wire.
On a quiet stretch of path I disturbed a couple indulging in what my local swimming pool used to refer to as necking or heavy petting.
It was busy at Portland Bill, the southern tip of the island, and everyone rushed into the cafe when the rain started.
Portland Bill Lighthouse
The walk along the east side of the island also went through disused quarries but was a lot lower and more sheltered from the increasing winds.
The rain was getting heavier and there wasn't much to see.
Church Ope Cove
The path followed a disused railway for a couple of miles under the cliffs.
With my hood up and head down I missed a sign that turned the path up the cliff and tramped on, through thickening wet vegetation, for half a mile only to come to a dead end and have to turn back.
Up on the cliff top the path went around the walls of the young offenders institute, through more post industrial scrub land, past the prison and down through the housing estates of Fortuneswell.
Sorry Portland, but I have rarely been to such a bleak and unattractive place.
It may be better in more clement weather but there would still be an awful lot of neglected ground and an abundance of barbed wire.
The weather was foul and I was soaked through.
The wind was whipping across the exposed road back to the mainland.
I was so cold that my hands were numb and could barely operate the phone to ring for a lift back from Weymouth.
I'm glad I wasn't camping in that weather.
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