Relationships with Contemporary Poets

His fellow Gaelic poets cherished Carolan. His closest friend was Charles Mac Cabe, Cathaoir Mac Cába, from Mullagh in county Cavan. Mac Cabe's first name was "Cathaoir", Irish for a chair as well as for Charles. His surname, "Cába" in Irish, also means a cape. So when the pair first met, Carolan asked him his name and was answered in a riddle: Tá m'ainm faoi mo thóin agus mo shloinne idir mo dhá shlinneán" ( My name is under my backside and my surname between my two shoulders). With the poet's insight Carolan instantly understood the riddle and welcomed him by name: "Cad míle fáilte romhat, a Chathail Mhic Cába" ( A hundred thousand welcomes to you, Charles Mac Cabe). After that, the two settled in for a long drinking session that lasted for some days.

People vividly remembered the antics of the pair. On one occasion while drinking, they had a wager that whoever fell asleep first would pay the night's bill. Mac Cabe was soon fast asleep. Carolan at once called for a sack and tied Mac Cabe in it, up to his neck, in case he would renege on the bet when he awakened. This episode led to a poetic contention between the pair, in which each wrote satirical verse against the other. The disparaging verses were good-humoured. The two were reconciled and later Mac Cabe turned the tables on his friend. On meeting Carolan once in Leitrim, Mac Cabe disguised his voice and told Carolan that the only news in the areas was the death of the wandering harper called Mac Cabe. Carolan was deeply upset and upon being led to the supposed grave, composed a poem of lament for his old friend.

Many Gaelic poets praised Carolan in verse, among them Séan Ó Gara of Sligo and Philip "Minister" Brady from Cavan.

Carolan composed music for the Irish verse of his friend Hugh Magauran, afterwards translated by Jonathan Swift as " An Irish Feast".

Carolan was taken by Colonel Maguire of Fermanagh to meet the County Louth poet Séamus Dall Mac Cuarta and the Armagh poet Patrick Mac Alindon, both of whom welcomed him in verse. MacAlindon's poem is addressed both to Carolan and Bridget Cruise. In the poem Bridget is speaking of her love for Carolan. Harps at the time were usually ornamented with a female figure. So Bridget is made to regret that she is not created in the form of a shapely harp:

" My destruction and my grief! That by God's miracles I have not happened to be a shapely harp; Not for the sake of wealth but for the sake of the fingers Of Ireland's lad of song: That he might take me gently to his bosom. . ."

Mac Cuarta's poem is a splendid tribute to Carolan who is shown as a conquering hero of music, coming from Cooley to Queen Maeve's territory of Connacht. The poem concludes:

"He will never want till death since he plays well; Every glint of sunshine the Father of grace gave to the master of the strings, This great master entranced the multitudes as he went It is only fitting to give him two million welcomes."