1882, 1 February Vladimir Dimitrov was born in the village of Frolosh, region of Kyustendil, in the family of generations of clergymen.
1889 – 1903 He lived with his family in Kyustendil. Due to the poverty of his family he left school to work. In the period of 1898 – 1903, while he worked as a clerk in the Regional Court of Kyustendil, he mixed with bright and intelligent young people from the town. During 1903 He had his first solo exhibition with drawings in the Pedagogical School in Kyustendil. With the financial support of the judge Nikola Chehlarov and his colleagues, he enrolled at the State Arts School (Fine Arts Academy) in Sofia.

1903 – 1910 He studied and graduated from the Fine Arts Academy in Sofia. Because of his outstanding talent, his colleagues called him “Maystora” (the Master). In his student years he visited Moscow, Odessa, Kiev, St. Petersburg (1909) and the Venice Biennial (1909) as well as Rome, Florence, Venice, Naples (1910).

1911 – 1918 He taught writing at the Secondary Trading School in the town of Svishtov. He made his first steps in considering his painting and changing the colours under the impact of open-air light.

1912 – 1918 He took part in the Balkan Wars (1912 – 1913, 1913) and World War I as a war artist. He created an impressive cycle of drawings and water colours with motifs of soldiers’ life (today, part of the collections of War History Museum in Sofia, National Art Gallery and Art Gallery – Kyustendil). He exhibited in the Bulgarian section of the exhibition of the Allied armies, which took place in1916 – 1917 in Berlin and Vienna.

1918 He left Svishtov and settled down in his home region of Kyustendil.

1919 He worked as a teacher in Sofia. He launched a solo exhibition with the help of his cousin Nikola Georgiev in the Art Gallery in “Aksakov” Street.

1922 He had a solo exhibition in “The Manege” in Sofia. He showed some of his first water colours
and oil paintings from the cycles “Harvest”, “Young Women”, and compositions on native
themes, with which he joined the Native Art movement that was typical of Bulgarian art at that
time. Contemporary critics saw his undoubted talent and original artistic means of expression.

1922, July – 1923, April He lived in Italy on the initiative of the Bulgarian artist Boris Georgiev (1888–1962). He created a number of official portraits to make a living. He participated with drawings in the Exhibition of Roman Artists. He met the American collector John Oliver Crane (1899–1982).

1924 – 1928 He worked for John Crane, аs he said, to whom he left more than 200 works – drawings, water colours and paintings – to pay his costs. Some of those works were returned to Bulgaria in the 1970s and 1980s and are now part of the collections of the National Art Gallery in Sofia and the Art Gallery in Kyustendil.
From March to May 1924 he stayed in New York, USA.

1924, autumn – 1926 He lived and worked in the village of Shishkovtsi, region of Kyustendil. He painted compositions on native themes.

1926 He had a solo exhibition in the Fine Arts Academy in Sofia; in April – October he worked in Istanbul.

1927, January He worked in Syracuse, Sicily and Roma. In May he showed his works from Istanbul and Syracuse in an improvised exhibition at Pavel Georgiev’s (his cousin) house in Sofia. The water colours (later called “Istanbul Cycle”) made a great impression on the modern-oriented audience with their expressiveness, unknown so far to Bulgarian painting.

1928 He terminated his contract with John Crane. He travelled in Czechia, Austria and Germany.

1930 – 1950 He worked as an artist at the Ministry of National Education. He settled down and lived in his home region, in the village of Shishkovtsi, until 1945. He actively painted in the villages of Divlya, Kalotintsi, Zemen, Ruzhdavitsa and others. He created great cycles of paintings, drawings and water colours that were connected with Bulgarian nature and the way of life of the local people. His models were real people from the villages like Stana Gogova from Ruzhdavitsa, old grandpa Stoyne from Divlya, Staniya from Kalotintsi, and Todorka Kamenova from Shishkovtsi.
Through the idealisation of the image, the artist recreated his notion of the moral beauty of
man. He sought the dimensions of the universal not only in his figure compositions but also in
his series of landscapes and fruits. The paintings with harvesters, madonnas and young girls from the 1930s underlined his entire work.

1935, 1938 He had solo exhibitions in Sofia, where he exhibited his mature painting.

1944, 6 August In the Mosque building at Kyustendil was opened the Historical Museum and it is standing exposition
with Majstora’s paintings, which was the beginning of Kyustendil Art Gallery. Today the
Art Gallery bearing the name of the painter possesses the biggest collection in Bulgaria of his
pieces of art.

1945 – 1960 He lived in Sofia. He was a delegate to the World Peace Council in Warsaw, 1948, Paris, 1949 and London, 1950.
He was awarded with the highest state insignia of honour for his contribution to Bulgarian culture. He had a number of solo exhibitions and participated in joined exhibitions of Bulgarian art both in the country and abroad. He stood out as one of the most significant and influential figures in Bulgarian fine arts culture.

1960, 29 September He died in Sofia. In 1972, his grave was moved to Shishkovtsi – the village that is most closely connected with Maystora’s life and work and which still cherishes the memory of the artist. The house where he lived has been turned into a museum.

1982 During the national celebration on the occasion of the 100th anniversary of the artist’s birth,
the Union of Bulgarian Artists established a painting award bearing his name.

Since 2002 The municipality of Kyustendil has organised international plenary events bearing the name of Maystora, which happen annually.