Clonakilty ("stone (castle) of the woods"), sometimes shortened to Clon, is a town in County Cork, Ireland. The town is located at the head of the tidal Clonakilty Bay. The rural hinterland is used mainly for dairy farming. The town's population as of 2016 was 4,592. The town is a tourism hub in West Cork, and was recognised as the "Best Town in Europe" in 2017, and "Best Place of the Year" in 2017 by the Royal Institute of the Architects of Ireland. Clonakilty is in the Cork South-West constituency, which has three seats.

The Clonakilty area has a number of ancient and pre-Celtic sites, including Lios na gCon ringfort.

Normans settlers built castles in the area, and a number of Norman surnames survive to the present day. In 1292, Thomas De Roach received a charter to hold a market every Monday at Kilgarriffe (then called Kyle Cofthy or Cowhig's Wood), close to where the present town now stands.

In the 14th century, a ten-mile strip of fallow woodland called Tuath na gCoillte (the land of the woods) divided the barony of Ibane (Ardfield) and Barryroe and reached the sea at Clonakilty Bay. Here a castle called Coyltes Castell was recorded in a 1378 plea roll. This was subsequently referred to as Cloghnykyltye, one of the many phonetic spellings for Cloch na gCoillte (meaning the castle of the woods, from 'cloch', the Irish for stone or stone building, and 'coillte' meaning woods).

Clonakilty benefited from the patronage of Richard Boyle, 1st Earl of Cork ('the Great Earl'), who is sometimes regarded as its founder. It was this Lord Cork who obtained its charter from King James I of England in 1613 with the right to return members to the Irish House of Commons. The borough of Clonakilty returned two members from 1613 to 1801; it was disenfranchised when the Act of Union came into force in January 1801.

The lands at Clonakilty were later purchased by the Earls of Shannon, another branch of the Boyle dynasty. They remained the main landlords of the town from the eighteenth century through until the early twentieth century.

During the Irish Rebellion of 1641, the planted English settlers in Clonakilty fled to Bandon, and much of Clonakilty was burned. English forces retook the town in 1642, in an attack where several hundred of the Confederate Irish forces were killed. Some later 18th century sources stated that English forces killed "238 men, women, and children" after retaking the town. The town was also the site of a battle in 1691, during the Williamite War in Ireland.

During the Irish Rebellion of 1798, Shannonvale near Clonakilty was the site of the Battle of the Big Cross. It was described as "the only place in all Munster where a blow of some sort had been struck during the Rising of '98". There is a commemorative statue celebrating the Battle of the Big Cross in Astna Square in the centre of Clonakilty.

Michael Collins, who was the Director of Intelligence for the IRA, which sought independence from Britain in the 1920-1921 period, lived in Clonakilty and attended the local boys' national school. Collins later served as Chairman of the Provisional Government and was instrumental in the founding of the Irish Free State. Collins was killed in an Anti-Treaty ambush during the Civil War. He gave several orations from O'Donovan's Hotel on the Main Street of Clonakilty. On Emmet Square, where Collins lived for a period, is a statue of Michael Collins (erected and dedicated in 2002) and a museum (opened in 2016).

In April 1943, a Boeing B-17 Flying Fortress was travelling from Morocco to England when it was forced to land at a marsh just outside Clonakilty. The crew (who were uninjured) thought they had been flying over German-occupied Norway.

Kennedy Gardens at Emmet Square (formerly Shannon Square) in the centre of town is named after John F. Kennedy.

In June 2012, Clonakilty was damaged by flooding.