Casterton boasts a fascinating array of art & craft galleries & collections. Any manner of handiwork can be found, including original oil and water-colour paintings, leadlight work, woodcraft, spinning, ceramics, card making, traditional dressmaking, quilting and even good old-fashioned knitting.
The Glenelg Shire Arts Program supports the visit of several touring performances to Casterton each year, offering a variety of shows including opera, music concerts and comedy. A local theatre restaurant regularly runs a variety of colourful musical comedy cabarets and local schools stage unique and special performances.
George Pentland (1871-1951) was a painter and interior decorator in Casterton, operating a business in Henty Street opposite the Post Office. He had a noted ability to paint friezes on walls. One of his valued clients was George Robertson Patterson of "Warrock" homestead where Pentland annually painted white the dozens of paddock gates. In 1889 Pentland painted a "bird's eye view" of Casterton looking north west. This painting now hangs in the Casterton Town Hall and is believed to be the only known painting to exist from his collection showing a view of Casterton. The painting, formerly in the custodianship of the Casterton and District Historical Society, was given to Glenelg Shire Council in 2008. The painting underwent extensive conservation work in 2010.