[5] As a landowner, Obolensky led "a country life reminiscent of Turgenev's tales" and as well as being a marshal of the nobility was a lover of nature, a patriot and an improver.
When news came of the Austro-Hungarian monitor bombardment of the Serbian city of Belgrade beginning on 29 July 1914, Obolensky spoke stirringly to the peasants on his estate of the need for war, and they reacted enthusiastically.
He later learned that his hearers had understood him to mean Belgorod near Kharkiv, which held the relics of the recently glorified Saint Ioasaph.
His wife was also descended from Prince Michael Vorontsov (1782–1856), an earlier Viceroy of the Caucasus, for whom Edward Blore designed the Alupka Palace near Yalta in the Crimea.
Early in 1919, during the Russian Civil War, and with Bolshevik armies approaching, he and his wife and children escaped from Russia on board the Royal Navy's HMS Marlborough, together with others who included the Dowager Empress Marie Feodorovna, the Grand Duke Nicholas, and Prince Felix Yusupov, the killer of Rasputin.
[3] Obolensky was somehow able to afford to send his son Dimitri to an English preparatory school, to the Lycée Pasteur, and to Trinity College, Cambridge, where he began a distinguished academic career which culminated in his becoming Professor of Russian and Balkan History at Oxford.