After gaining his freedom Skitalets's father spent some time as a village bartender and later took to wandering through Russia, with his young son in tow, the two making a living together as street and barroom musicians for several years.

[2] During the years of wandering with his father he often experienced want and bad conditions, but he was also able to collect a wealth of experiences, meeting different people and travelling widely throughout Russia.

[3][4] After being expelled from the Samara Teacher's Seminary in 1887 under suspicion of political radicalism, he went out on his own in southern Russia, working as a clerk, actor, singer, writing for several papers, and taking part in the student revolutionary movement.

[1] Skitalets came to Moscow with Gorky where he joined the Sreda, a literary group founded by the writer Nikolay Teleshov, which included many of Russia's most popular authors and artists, such as Leonid Andreyev, Ivan Bunin, Fyodor Chaliapin, Gorky and, when he was in town, Anton Chekhov.

One of his songs, which he first sang at a meeting of the Sreda, was included in the beginning of the second act of Gorky's play The Lower Depths.

[1] He continued publishing his works separately and in collected editions through the years leading up to World War I and the Russian Revolution of 1917.