Portland and Weymouth to Poole Walking Blog

Day 1 Sunday 11th October 2020

Drove to Weymouth and spent the night at the Gloucester House B&B, didn’t eat out as we arrived late and tired.

Day 2 Portland (Fortuneswell to Fortuneswell) 9 miles 12 October

Having stayed overnight at Gloucester House B&B in Weymouth we drove to Fortuneswell and parked in a free car park.  The walk starts with a steady climb and you can look back and get a wonderful view of Chesil Beach.  We walked along cliff tops next to old quarries with the occasional diversion due to land slip. We fairly quickly arrived at Portland Bill, by this time the rain had started.  We got some pictures of the lighthouse and then went into the Lobster Pot for some early lunch.  It had very strict Covid precautions and we were slightly underwhelmed by the coffee and sandwiches which also seemed a bit pricey.  Would have been a lot nicer if the sun had been shining and we could have sat outside enjoying the marvellous views.

Day 2 after lunch

Afterward we were back on a path along low cliffs, we the climbed up to Rufus Castle and then along a track which took us in front of large cliffs.  We arrived at a dead end by by the sea.  We then had to back track ½ a mile before finding a right turn with the sign missing.  This path took us up a path through the cliffs and to the outside of the jail.  The path took us around the big fenced and razor wired walls of the jail.  A little further on there was a a fenced farm with lots of little kangaroos.  They have a small café though we didn’t stop.  The path is goes back across the island and after coming across huge stone works a sign that told us the prison was originally a fort and had been converted in the late 1940s, we soon dropped back down into Fortuneswell and the end of the days walk.

We again stayed another night at the excellent Gloucester House B&B and enjoyed a top quality meal at Shalim’s Balti House a short walk away.

Day 3 Weymouth to Lulworth 11 miles

Sunny morning nice stroll down Weymouth sea front, we had a coffee at Oasis café before leaving the beach walking up and then thru a holiday park and behind a huge but decaying hotel. After a while arrived at Osmington Mills and the path goes thru the pub gardens. We decided it was too early for lunch and pushed on. The path then follows the rolling hills, some big climbs and fantastic views of white cliffs arriving first at Durdle Door and then on to Lulworth Cove.  Both fantastic but the tranquility of the path was disturbed by the relatively large crowds at both.  We had a drink at Lulworth Cove before walking up the road to West Lulworth and our overnight stop at the Castle Inn.  We had an excellent supper there of a sharing fish platter followed by sticky toffee pudding.

Day 4 Kemmeridge Bay to Worth Matravers via St Andhelm’s Head 9 miles

The day should have started with a wonderful walk of 6.5 miles to Kemmeridge Bay across the army ranges, however unless you time your walk to the weekend the ranges are invariably closed.  This morning they were closed and the only walking option was a 12.5 mile road walk to Kemmeridge Bay.  The alternative was a 20 min taxi ride.  The B3070 is a fairly busy road and the choice was a simple one.


A leisurely breakfast and a 10:30 pickup by taxi.  £35 later we were dropped off in the car park of Clavell café at 11:00.  Although the café did not open until 11:30 the wonderful girl at the counter sold us 2 coffees to go, customer service par excellence!  A short walk down the road got us to Kemmeridge Bay where we scoured the beach for a few fossils, very easy to find.  The sun was shining and the scenery superb a wonderful walk along the cliffs with rolling countryside to our left.  Eventually we arrived at the bottom of Houns Tout Cliff and our longest climb yet, a real slog but we treated ourselves to lunch at the top.  A steep descent was followed by some relaxed inland walking around Chapman’s Pool. We decided as it was still early to press on to St Aldhelm’s Head, a steep ascent with 219 steps, before turning inland to walk the 1.75 miles to our overnight stop in Worth Matravers. We stopped at the Square and Compass pub for a pint and a pasty.  I had the local cider , 7.1% alcohol, which nearly knocked me over! Then onto Chiltern Lodge our b&b.  We had supper at the B&B as the local pub was not doing meals.

Day 5 Worth Matravers to South Haven Point and on to Poole 14 miles.

A long day so we set off at 09:15, a relief to leave the B&B as the owners were so worried about Covid-19 that the atmosphere was not great.  We walked thru Worth Matravers and down a path to Winspit Quarry where we rejoined the path.  It was a beautiful morning and great walking along the cliff tops, we anticipated getting a mid-morning coffee at Swanage but it was a bit further than we thought and we arrived there at 12:00.  Some local walkers we had met on the way recommended the Salt Pig and we had a lunch of a soup and a sandwich there, which was very good.  With a solid 7.5 miles to South Haven Point still to go we were on our way again before 13:00.  We meandered past houses and chalets as we departed Swanage before a steady climb and then along the tops to Old Harry Rocks.  We were treated to a parachute display by the army who were jumping out of a Hercules and landing in Studland Bay.  After passing various cafes and a pub we arrived at Studland Beach and with the tide out were able to walk all along its length to South Haven Point and the end of the path.  We caught the ferry to Sandbanks and had a further 1.5 miles to walk to The Sandbanks Hotel.  We had 1.5 hours to recover before our booking at Rick Stein’s Restaurant for a celebratory end of walk meal.  An excellent way to finish.

Day 6 Poole to Weymouth and then back to Cornwall.

We caught a taxi to The Bus Station in Poole and then took the 10:00 X54 Pool to Weymouth Bus. We arrived back in Weymouth at 11:35 and then had a 3 hour drive back to Cornwall.