Grammy-winning producer Kaytranada will return to South Africa in December for the third Milk + Cookies festival, while British singer Olivia Dean is scheduled to headline the event’s first 2027 dates, Sowetan reports.
Kaytranada is set to perform at Kenilworth in Cape Town on December 18, followed by a Johannesburg show at Nasrec on December 20. His brother Lou Phelps is listed for the Cape Town date alongside Jinji, Kid Fonque, Kudbeu, Mamthug and Tumi Moliko. The Johannesburg line-up includes MCHLSN, Muzi, Shamiso, Thakzin and Yolophonik.
The producer previously headlined the festival’s inaugural edition in 2025 and performed at Afropunk Joburg in 2019. The event’s organisers have described the programme as a gathering built around music and wider cultural experiences, including fashion, wellness and community events.
Olivia Dean opens the 2027 programme
Dean is scheduled to perform at Sandringham Farm in Cape Town on January 29, with the Johannesburg date set for Nasrec Expo Centre on January 31. Sowetan lists Elaine, Zee Nxumalo, Chelsea Sloan and Jade T among the artists joining her.
Both shows extend the festival across the year-end and into the start of 2027, pairing international headliners with South African performers. The programme also includes activities beyond the stage, with Sowetan reporting plans for yacht parties, industry panels, writing workshops and other events.
Chase Freeman, Milk + Cookies’ head of marketing, told Sowetan the festival’s choices were intended to bring varied sounds together around a shared audience and experience. The announced dates give local fans an opportunity to see Kaytranada at the end of this year and Dean early next year, while the supporting acts provide a platform for South African artists.
Source: Sowetan, “Kaytranada returns to SA to round off 2026 and set the tone for 2027,” by Masego Seemela, 9 November 2026. This is an original Sunday Express report based on that coverage.