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A mounted white horse representing King George III is carved into the chalk hills of Osmington. The horse faces away from the town, and a myth developed that the king took offence, believing it was a sign that the townspeople did not welcome him, and that the designer subsequently killed himself.

Weymouth's esplanade is composed of Georgian terraces, which have been converted into apartments, shops, hotels and guest houses. The buildings were constructed in the Georgian and Regency periods between 1770 and 1855, designed by architects such as James Hamilton, and were commissioned by wealthy businessmen, including those that were involved in the growth of Bath. These terraces form a long, continuous arc of buildings which face Weymouth Bay along the esplanade, which also features the multi-coloured Jubilee Clock, erected in 1887 to mark the 50th year of Queen Victoria's reign. Statues of Victoria, George III and Sir Henry Edwards, Member of Parliament for the borough from 1867 to 1885, and two war memorials stand along the Esplanade.

In the centre of the town lies Weymouth Harbour; although it was the reason for the town's foundation, the harbour separates the two areas of Melcombe Regis (the main town centre) and Weymouth (the southern harbourside) from each other. Since the 18th century this has been overcome with successive bridges over the narrowest part of the harbour. The present Town Bridge, built in 1930, is a lifting bascule bridge to let boats access the inner harbour, one of ten in the United Kingdom.

Weymouth and Portland were bombed by German planes for their role in World War II; Portland harbour had a large naval base, and Weymouth was home to Nothe Fort. 517,816 troops embarked through the borough to fight at the Battle of Normandy, and the Bouncing bomb was tested in the Fleet lagoon to the west of town. The history of the area is documented at the Timewalk Museum in Brewers Quay; the former brewery is a tourist attraction and shopping village on the southern shore of Weymouth Harbour.

The district of Weymouth and Portland was formed on 1 April 1974 under the Local Government Act 1972, and merged the borough of Weymouth and Melcombe Regis and the nearby Portland urban district. For local elections the district is divided into 15 wards, 12 of them in Weymouth. Elections take place in a four-year cycle; one third of the councillors in all but three wards retire or seek re-election in years one, two and three, and county council elections are held in year four. The Mayor of Weymouth and Portland is David Harris (Liberal Democrat), and Tim Munro (Independent) is Deputy Mayor.

Weymouth, Portland and the Purbeck district are in the South Dorset parliamentary constituency, created in 1885. The constituency elects one Member of Parliament; currently Jim Knight (Labour), the Minister of State for Schools. South Dorset, the rest of South West England, and Gibraltar are in the South West England constituency of the European Parliament.

Dorset South was the most marginal Labour seat in the 2001 general election, won by 153 votes. Jim Knight was expecting to have a difficult 2005 election, yet he won with a margin of 1,812 votes this was in contrast to other areas, where Labour suffered a decline in popularity. This was helped by a high-profile anti-Conservative campaign by musician Billy Bragg.

Weymouth and Portland have been twinned with the town of Holzwickede in North Rhine-Westphalia, Germany since 1986, and the French town of Louviers, in the department of Eure in Normandy, since 1959.