Portland Harbour is one of the largest man made harbours in the world, enclosed by breakwaters built in the nineteenth century, partly by convict labour, from Portland stone quarried on the island above. For over a century it was a major Royal Navy base, and today it is a centre for sailing, windsurfing and kite surfing; the sailing events of the 2012 London Olympics were held here. The shore between Weymouth and Portland, with Chesil Beach stretching away to the west, is a fascinating place to explore.
The Isle of Portland, linked to the mainland by a narrow causeway and the end of Chesil Beach, is a block of limestone, famous for its stone, which was used to build St Paul's Cathedral, Buckingham Palace and many other buildings. The island has quarries, prisons, lighthouses and wild cliffs, and the views from the top over Chesil Beach and the harbour are spectacular. Chesil Beach itself, a shingle bank about eighteen miles long, has pebbles graded by size along its length, from pea sized at the west end to fist sized at Portland.
The riding here is a mix of town and coast. Weymouth is a busy seaside resort, with traffic in summer, and the road to Portland crosses the causeway and climbs steeply to the top of the island. The roads on Portland are narrow and twisty, with views on every side. The coast road west from Weymouth toward Abbotsbury and Bridport is one of the finest in Dorset, with views over Chesil Beach and the Fleet lagoon.
Weymouth has filling stations and supermarkets on its outskirts, and the old harbour area is lively, with pubs and restaurants. Portland has its own services. In the pubs, try local ales and seafood, especially crab and lobster from the Dorset coast. The weather here can be windy, which is great for sailors but less so for riders.