Among the best known and most popular streets in the city, the Cuba precinct has been labelled Wellington's cultural centre, and is known for its high-per-capita arts scene the world over.

[2][6] Developed at the point of colonisation on Te Āti Awa land, Cuba Street runs south from the CBD of Wellington in the inner city, and was originally full of very basic homes built into the forest, such as "the Old Shebang".

From the 1970s to early 80s, the street became the red light district of Wellington, and a sign of solidarity against New Zealand's laws making homosexual acts illegal until 1986.

The street was named by Captain William Mein Smith the first Surveyor General after an early New Zealand Company settler ship, the Cuba, which he arrived in Wellington Harbour on 3 January 1840.

After the tramlines were removed and following public pressure the middle section of the street closed to traffic in 1969 to become a pedestrian mall and has remained so.

Mary Taylor (1817–1893), lifelong friend and correspondent of author Charlotte Brontë, owned and ran a small Cuba Street general store, from c. 1840 to 1860.

[20] Cuba Street is described as the bohemian creative area of Wellington, and is the home to many cafes, op-shops, boutique fashion stores, art galleries, and music shops.

Glover Park was a regular hangout of rough sleepers and a council Public Places Bylaw that was reviewed in 2004 meant they were getting evicted which essentially moved them into Cuba Mall.

[24][25] Pedestrian light signals in her likeness were put up at four intersections along Cuba Street in 2016 to coincide with the 30-year anniversary of the Homosexual Law Reform Bill coming into effect.