The fictional Southwold Estate, seat of the equally fictional Earls of Southwold, is the country estate of the family of Lady Marjorie Bellamy in the ITV British drama Upstairs, Downstairs. The town and its vicinity has been used as the setting for numerous films and television programmes, including Iris about the life of Iris Murdoch starring Judi Dench; Drowning by Numbers by Peter Greenaway; Kavanagh QC starring John Thaw; 'East of Ipswich' by Michael Palin; Little Britain with Matt Lucas and David Walliams; and a 1969 version of David Copperfield.
The BBC children's series Grandpa in My Pocket is filmed in Southwold, Walberswick and Aldeburgh. Only exteriors of buildings were filmed – no acting was done there.
ITV drama, A Mother's Son, was recently filmed on location in Southwold. It was broadcast on ITV1 in September 2012.
Julie Myerson, setting her 2003 murder novel Something Might Happen in an unnamed Southwold, calls it "a sleepy, slightly self-satisfied seaside town". The town isn't named, but Myerson stated that setting a murder in the car park did make her feel as if she "was soiling something really good". She holidayed in the town as a child and remarked in an interview that while everything else in her life had changed, her mother and Southwold had remained the same. She still owns a second home in the town.
Other books set in Southwold include Esther Freud's novel Sea House with Southwold as Steerborough Southwold native Neil Bell in Bredon and Sons (1933, about boat-building people) and Forgive us our Trespasses (1947, based on a true story of twin boys lost at sea) renames the town Senwich. The Bookshop by Penelope Fitzgerald (1978) drew on her experiences working in a Southwold bookshop in the 1950s. An earlier book thought to be set in Southwold is Beside the Guns (1902) by the Christian author Mary Elizabeth Shipley. The German writer W. G. Sebald describes Southwold in The Rings of Saturn, an account of a walk through East Anglia.
Orwell's home in Southwold
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The writer George Orwell spent time as a teenager and in his thirties in Southwold, living at his parents' home. A plaque can be seen next door to what is now the fish and chip shop at the far end of the High Street.
From January to June 1922 he attended a cramming establishment in Southwold to prepare for his Indian Police Service exams and his career in Burma. In 1929 after eighteen months in Paris he returned to the family home at Southwold and spent most of the next five years based at Southwold. He tutored a disabled child and a family of three boys during this time and wrote reviews and developed Burmese Days. During this period he spent nearly eighteen months teaching in West London until he had a serious bout of pneumonia. His mother then insisted that he stay at home instead of carrying on teaching and he spent the time writing A Clergyman's Daughter. The novel is partly set in a fictionalised East Anglian town called "Knype Hill". His final visit to Southwold was in 1939.
The town has a history of hosting summer repertory theatre, staged by different companies. For several years, Suffolk Summer Theatres have offered a varied programme of plays from July to September, which are staged in St. Edmund's Hall.
Annually, in November, the "Ways with Words" literature festival is held in the town, with many notable speakers appearing at different venues.
The year 2014 saw the staging of the inaugural Southwold Arts Festival, which was to be repeated in future years. It offers a mix of literature, music, film and art exhibitions, with the main events occurring over an eight-day period in the summer. The festival continues its legacy of bringing entertainers of diverse backgrounds together.
In 2005, Southwold launched Suffolk's "answer to the Turner prize", the "Flying Egg" competition. This event also ran in 2006 and 2007, but was not repeated in 2008.