Olivia Dean will headline Milk + Cookies Festival 2027, performing at Sandringham Farm in Cape Town on Friday, 29 January and at the Nasrec Expo Centre in Johannesburg on Sunday, 31 January 2027.
The Grammy and BRIT Award winner is the festival’s third South African headliner, after Kaytranada in 2025 and Gunna in 2026. She joins a line-up that already includes Elaine, Zee Nxumalo, Chelsea Sloan and Jade T, with further acts and the full programme still to come.
When and where is Olivia Dean playing in South Africa?
The Cape Town show takes place on Friday, 29 January 2027, with Johannesburg following on Sunday, 31 January 2027. Both dates were confirmed in September when the festival announced its return for a third year.
Cape Town’s show moves to Sandringham Farm, the festival’s third venue in the city after Ostrich Farm in 2025 and Hollywoodbets Kenilworth Racecourse in 2026. Johannesburg returns to the Nasrec Expo Centre, which hosted the 2026 edition.
How to get Milk + Cookies Festival 2027 tickets
Pre-registration for early access to presale tickets is open on the festival’s ticketing website. Presale starts on Wednesday, 28 October 2026 at 10:00 SAST, and general sales open on Friday, 30 October 2026 through Howler for both cities.
Who is Olivia Dean?
Dean, a British singer-songwriter, won the Grammy for Best New Artist in February 2026 and went on to win four BRIT Awards, including Album of the Year for The Art of Loving and Song of the Year for Rein Me In, her collaboration with Sam Fender. The Art of Loving is her second album and was released on 26 September 2025.
Her grandmother, Carmen, left Guyana for London at 18 as part of the Windrush generation. Accepting the Grammy, Dean opened with, “I want to say I’m up here as a granddaughter of an immigrant,” before adding:
“I’m a product of bravery, and I think those people deserve to be celebrated.”
Olivia Dean, accepting the Grammy for Best New Artist
Who has headlined Milk + Cookies Festival before?
Kaytranada opened the first South African edition in 2025 in front of 20 000 people, and Gunna headlined the 2026 edition. Elaine was the first local act confirmed for 2027, on Friday, 9 October 2026, followed by Zee Nxumalo and Jade T on Thursday, 22 October 2026.
Chase Freeman, Head of Marketing at Milk + Cookies, said the festival has used the same booking brief for three editions, and that building it with South Africans has changed how the team works everywhere else:
“People keep asking how Kaytranada, Gunna and Olivia Dean end up on the same bill. Never the same sound, always the same feeling. That’s the only brief we’ve ever had. We book for the people in the room, not for a genre, and they come for what the room feels like as much as the name on the poster. Three years in, that’s what South Africa has given us. We came here to put on a show and ended up building something with the people who live here, and it’s changed how we do this everywhere else.”
Chase Freeman, Head of Marketing at Milk + Cookies
Sources
- Milk + Cookies Festival, media release "Olivia Dean to Headline Milk + Cookies Festival South Africa 2027", issued 23 October 2026
- Milk + Cookies Festival, media release issued 27 September 2026
- Milk + Cookies Festival, official website
- WALB, Olivia Dean wins best new artist at the 2026 Grammy Awards (2 February 2026)
- uDiscover Music, Olivia Dean, Sam Fender, and Lola Young win at the 2026 BRIT Awards (2 March 2026)
- Swisher Post, Milk + Cookies Festival 2027: What we know so far
- Swisher Post, Milk and Cookies Festival Cape Town review
- Swisher Post, Kaytranada live in South Africa
