Weymouth to Portland

Wednesday 23rd July 2025

The weather looked a little iffy again today so we made a last minute decision to tick off another 5.5 miles, completing a gap between Weymouth and where we finished off yesterday, at the Cove House Inn in Portland.

A beautiful and mostly straightforward route – just one section which showed on our OS app as a coastal path but we would definitely not recommend it to fellow walkers. It was the path linking the top of Bincleaves to Castle Cove. It started off OK but became more and more overgrown, also extremely narrow with an unnerving drop to the left. A mile in and we had to make the decision to either turn back or tackle some uncomfortable climbing and slopes. Decided on the latter and literally took a step at a time, me clinging on to Steve, trees, shrubs, anything that came to hand. Definitely not for the faint hearted and I wouldn’t be doing it again.

Absolutely easy walk after that and we rewarded ourselves with a few beers at the end.

The isle of Portland – a day of spectacular views

Tuesday 22nd July 2025

So I’ve been chilling down in sunny Weymouth for a couple of weeks, lapping up lazy days on the beach, swimming, playing tennis, plenty of dining and drinking opportunities with family and friends, the odd leisurely stroll … and then Steve arrives which can only mean one thing – Coastal Walking!!!!

It hadn’t actually been our intention but as the weather took a little turn and we still had some sections to cover down this way it seemed like a good idea. We chose to walk the beautiful island of Portland today, not far from where we are staying. We caught the bus from Weymouth Harbour up to the Portland Sailing Academy where we set off to tackle the infamous rugged and hilly paths.

Just past Portland Castle, we veered off to the right and boy did we go uphill, it was relentless. Believe it or not, this steep two mile path had previously been a horse drawn and cable operated incline railway, built for the island’s stone trade in 1826, from the working quarries at Tophill to a shipping pier at Castletown. Needless to say, it took a lot of effort, heavy breathing and rest breaks to reach the summit … and we kidded ourselves that that would be it for climbing, it surely must be all downhill now!!

The long climb up from Portland Harbour

The path took us around the two prisons, one in which Mr. Glitter and his gang of inmates reside – very rock and roll. Amongst the grimness of the stark grey buildings we constantly had the most spectacular views to our left, of the sailing activity in Portland Harbour, the Dorset coastline and fabulously blue seas.

Occasionally we wandered through woodland areas and many paths lined with vibrant purple buddleia, attracting a variety of butterflies. We were also surprised at the number of fully ripe blackberries – seems so early. The pretty path led us down numerous steps to Church Ope Cove then steeply upwards again to the gothic revival mansion Pennsylvania Castle. From here there was a little roadside walking until we picked up a cliff top path all the way to Portland Bill. Most of today’s path was pretty rugged underfoot (not to mention the hills) which made progress a little slow – but it’s not a race!

Church Ope Cove

Beautiful buddleia

7 miles in we took a rest at Portland Bill, enjoyed a cup of tea from the famous ‘Lobster Pot’ and, having built an appetite, devoured our egg and spring onion sandwiches (eggs lovingly supplied, hard boiled and mashed with mayo by my sister Caroline).

Pulpit Rock

Feeling replete we set off to walk the other side of the island. This was an extremely long but steady incline, once again with the most wonderful views, this time of the 18 mile stretch of Chesil Beach and West Dorset. We hit a couple of areas where the path was closed due to cliff falls and were diverted inland a little – one section taking us through a disused quarry which has become a sculpture park.

Sculpture Park

The final stretch at Underhill was a steep and rocky descent, some steps provided in places but I still managed to take a tumble backwards, despite having remembered my walking pole this time. We ended our walk in Chiswell at The Cove House Inn, luxuriating in a long cold drink – lime and soda for me and something a little stronger for the big man.

The glorious Chesil Beach

Another 11 miles ticked off. Bus back to Weymouth and a little rest before going to meet friends on the beach tonight for drinks, music and dancing!