The River Ilen runs through the town; it reaches the sea about 12 kilometres away, at the seaside village of Baltimore.

In his book The Origin and History of Irish Names of Places (1869), the historian Patrick Weston Joyce suggests that the Irish place name Sciobairín or Scibirín derives from the small boats or skiffs (scibs) that were common on this stretch of the river.

[6] A statue, the 'Maid of Erin' erected in 1904, sits on top of a memorial to commemorate four failed uprisings against British rule, the dates of which are engraved on each side of the plinth: 1798, 1803, 1848, 1867.

[14] A permanent exhibition to commemorate the memory of the victims of the Great Famine is sited at the Skibbereen Heritage Centre.

[16] The National Famine Commemoration Committee agreed that the centrepiece of the memorial day would rotate between the Four Provinces on an annual basis.

The local secondary school St. Fachtna's was a finalist in 1982 and a winner in 1991 of the Hogan Cup for Gaelic football.

[29][30] As of 2016, 5.4% of Skibbereen's urban population identified with a UK nationality,[31] compared to an average of 2.6% for the county as a whole.

This typically takes place at the end of July and includes community-based projects as well film screenings, theatre, visual art and music acts.

[citation needed] Skibbereen has also hosted the Cork X Southwest Music & Arts Festival over several years.

The 2011 festival was held at Liss Ard Estate and featured Patti Smith, Echo & the Bunnymen, Balkan Beat Box, Fred and others across a two-day lineup.