The Berrima Districts first newspaper was the Burrawang Times, which was registered by Thomas Corcoran on the 13th of August 1863. In 1880 William Webb founded the Burrawang Herald and it came into existence, he sold it in 1884 to Barrett and Moses of Burrawang and it stopped publication in 1893.

On the 7th of July 1883 the Bowral Free Press appeared and was owned by William Webb who sold it in March 1884 to William and Daniel Beer. In February 1885 Daniel Beer became the sole publisher and after his death in November 1891 his widow took over in September 1895 and sold it to William Beer. In March 1906 the name of the journal changed to the Wollondilly Free Press but ended publication after the 1st of July 1914. In 1880 Daniel Beer published the Royal Monthly but it didn't last long. In October 1884 the Intelligence was produced by the Bowral Free Press but ended a month later.

Daniel Beer began to publish a paper in Mittagong called the Mittagong Mail, which first appeared on the 9th of September 1885. Beer sold the paper to JC Murphy in January 1886 who changed its name to the Southern Mail after registering it on the 30th of December 1886. In July 1887 Murphy registered the Robertson Advocate and then the Moss Vale Record in 1888 The Southern Mail and TC Brown and C Stubbings bought other papers run by Murphy in March 1893. In 1898 they ran into financial difficulties and sold the Mail to J White, B Moule and A Holmes. A Holmes later withdrew from the firm and in April 1910 the two partners registered the Southern Mail, Robertson Advocate, Moss Vale Record and Mittagong Express, which they continued to publish until November 1923 when Hector Lamond acquired them. Hector Lamond had been the editor of the Worker for years and also acted as manager, he had been MHR for Illawarra and a former Honorary Minister in the Second National War Government. He registered the Southern Mail on the 24th of October and also renamed the three other papers the Mail also producing the Four Mails. He published all of them until his death on the 26th of April 1947 and his son HS Lamond became managing editor.


Bowral depended on local talent as entertainment for many years. The Bowral Amateur Minstrels gave their first performance in August 1885 with the organisation being one of the first of its kind in town. In October 1885 a lot of entertainment was provided. RP Booth, a travelling orator, spoke about "Reminiscences of the American War", another orator spoke about Tennyson's Enoch Arden and the Mittagong Amateur Dramatic Club gave entertainment. The Lynch family of Bell Ringers made their first appearance in Bowral and then frequented thereafter to the early 1900's. Popular entertainment also came from the Fisk Jubilee Singers and Marie Narelle.

In 1907 Neville Vaudeville's Company did some shows. In 1908 Weston's Circus and Buckjumping Show was popular. In 1908-1912 Maurice Gerald's Dramatic Company visited the town. In 1909 Dan Barry's Dramatic Company staged Uncle Toms Cabin. In 1927 the Amitie Club formed and continued until 1940 and it was revived in 1946 and performed 4 plays at the School of Arts.

In June 1901 the moving picture show arrived when the Federal Bioscope and Concert Company first appeared in the School of Arts but attendance was not encouraging. In 1906 the Electric Biorama Company visited. In 1907 HC Inlays Moving Pictures were shown with prices at 2/- and 1/-. For two nights in April 1908 Lances Animated Pictures Company put on shows, which were described as the best ever seen in town. Wild Beasts at Home and Toilers of the Sea were shown. In 1908 Spencer's Pictures made a visit to Bowral with the show being a mixture of films and vaudeville acts. A weekly show at the School of Arts by the Victor Picture Company began with a change of program each week, the cost was 1/-. In 1911 Colliers Biograph visited Bowral showing a large variety of pictures including the launching of HMAS Warrego and the flight between Langford and St Ague. A megaphone provided music. The Sydney Lyceum Pictures made visits to Bowral in 1914. In June 1914 Hazell's Photo Plays put a show on using a full electric machine, prices were 1/- and 9d.

All these shows staged silent pictures and had to provide their own electric power. They did this by fixing a dynamo to a motor lorry with the shows working in a number of country towns.

In 1915 WW Arnett built a brick hall in Bong Bong Street and leased it to WJ Painter to use as a cinema that was named the Empire Cinema. Pictures were shown twice a week with skaters using the hall twice a week in the season. The lessee installed a gas engine and a 110-volt dynamo to provide current. HR Painter directed the show with prices at: dress circle1/6, stalls 1/- and front seats 6d. The 14th of September saw the first program shown with over 500 people attending the opening night. The picture shown was Charlie Chaplin's The Property Man and an Australian Gazette with the local orchestra providing music. From 1916 to 1920 the Sutton's Star Pictures exhibited films in the School of Arts. The picture The Gentleman Bushranger that was filmed in the area was shown to large audiences in Bowral and Mittagong. In 1925 the Empire Cinema was extended and improvements to the building that was said to have transformed Bong Bong Street. The Empire Cinema showed the picture Talkies in October 1930 and the cinema was now open 3 nights a week. In 1935 more extensions to the cinema were done and it re-opened on the 18th of December 1935. In September 1954 Bowral was the second country town to have a picture theatre with a Cinemascope installed with the film shown being The Robe, which is 20th Century Fox Film.