While the autumn days get shorter and the rain clouds begin to form, Cape Town’s event season keeps on going. Read on to find out everything happening in the month of May, from comedy and beer festivals to iconic marathons and acclaimed opera productions.
This page is updated throughout the month, so keep an eye on it to find out about many of the big and small events happening in the Mother City.
SANLAM Cape Town Marathon
After cancellation in 2025, the Sanlam Cape Town Marathon is back, and is currently on track to be Africa’s first Abbott World Marathon Majors candidate, the list of the most renowned marathon races across the world.
This global urban, fast-paced marathon is suited to a range of running enthusiasts from social runners to elite athletes. With the entries closed and the route extending throughout the Mother City, there are many places for friends and family to watch the runners on the day. The organisation has posted a spectator’s guide so viewers can plan where to stand and support.
Date: Friday & Saturday, 23 & 24 May 2026 | From 6am
Where: Start at Fritz Sonnenberg Road, Green Point Stadium, Cape Town
Bongeziwe Mabandla
The Johannesburg-born soul singer returns to Cape Town with a bold new direction in his musical journey.
Following a first European tour, Bongeziwe Mabandla is set to embark on a nationwide series of shows. With a sound that harkens back to traditional Xhosa folk, this show explores his journey to becoming a soul icon with a fresh set of songs.
Blending an intimate atmosphere with Bongeziwe’s introspective writing, the performance promises to be a soulful introduction to a new era.
Cost: R250 – R400. Book now on Quicket.
When: 29 May 2026 | 7pm – 10pm
Where: Hearty Collective, Old Biscuit Mill, 375 Albert Rd, Woodstock, Cape Town
Bed By 10: LGBTQIA+ Edition
The global clubbing phenomenon, Bed by 10, is back in Cape Town, with an event specifically for the queer community. For those who are fed up with late nights and hungover mornings, Bed by 10 is a unique daytime clubbing experience that lets partygoers relive the bangers of the ’80s, ’90s and ’00s while still getting into bed and falling asleep by 10pm.
Dancers can expect DJ-spun classics, glitter, and camp chaos. This edition is for individuals 25+, though anyone 18+ can join.
Cost: From R300. Final release tickets available now on the website.
When: 30 May 2026 | 4pm – 9pm
Where: District, 61 Harrington St, Cape Town City Centre
ACDC Duet Xchange
The Mother City has a new platform for watching, celebrating, and crowning some of South Africa’s best choreographers. Presented by Anderson Carvalho Dance & Choreography (ACDC), the bi-annual competition and performance platform is an opportunity to grow the country’s dance movement, with collaboration and original works in the spotlight.
The event is split into a two-day programme: the first features collaborative performances by some of Cape Town’s leading choreographers, and the second is a high-stakes competition between up-and-coming professionals competing for prizes.
Cost: R150 per night. Book now on Webtickets.
When: 22 & 23 May 2026 | From 7pm
Where: Star Theatre, Homecoming Centre, cnr Caledon & Buitenkant Sts, District Six, Cape Town
Boyz II Men Live Tour
One of the world’s most celebrated R&B groups, Boyz II Men, is returning to Mzansi for the first time in years on their Live South African Tour.
With four Grammy Awards, nine American Music Awards, multiple Billboard Music Awards, and sales exceeding 60 million albums worldwide, Boyz II Men continue to influence generations of artists and captivate audiences with their polished vocals and exceptional live performances.
Presented courtesy of Remoakantse Holdings, the Cape Town show brings local music lovers a world-class production featuring timeless hits such as ‘End of the Road’, ‘I’ll Make Love to You’, ‘On Bended Knee’, ‘Water Runs Dry’ and ‘Motownphilly’, among many others.
Cost: R750 – R1450pp. Online sales sold out on Webtickets.
When: 27 May 2026 | From 6pm
Where: Grand Arena, GrandWest, 1 Jakes Gerwel Dr, Acacia Park, Cape Town
The Good Life Show – Cape Town 2026
The 2026 season of The Good Life Show begins in Cape Town, showcasing the very best of ‘good-for-you’ food, ‘better-for-you’ lifestyle, home and beauty innovations, uniquely African superfoods, culinary experiences, emerging talent, and future-fit farming and sustainable food systems.
Visitors can sip, taste, touch, smell and explore a curated marketplace of innovative brands, immerse themselves in chef demonstrations from leading local and continental culinary innovators, experience bold African flavours and contemporary food culture, engage in workshops and masterclasses and mingle with experts shaping the future of food, health and sustainable living.
Cost: R150 per person (Day Pass). R230 per person (Two-Day Pass) | Children under 12 free. Book via Quicket.
When: 29 – 31 May 2026 | 10am – 6pm (Fri & Sat) | 10am – 4pm (Sun)
Where: Cape Town International Convention Centre (CTICC 2), Convention Square, 1 Lower Long Street, Cape Town
BeerEx Africa
Created with the goal of growing the African beer industry, this multi-faceted event includes everything from inspirational seminars by professional brewers, interactive demos of innovative products in the space, and (of course) beer-tasting experiences from various brands and labels.
In the evenings, various bars and craft breweries host a range of social, beer-related events, before the weekend finishes off with The African Beer Cup – the continent’s biggest beer competition, where national champions are crowned.
Cost: From R150 | Access to all events sold separately. Book now on Quicket.
When: 21 – 23 May 2026 | Times vary per event
Where: The Wicket Expo Hall @ Newlands Cricket Ground, 146 Campground Rd, Newlands, Cape Town
Rise ’76: The Story of June 16th
To mark the 50th anniversary of the 1976 Youth Uprisings, two-time Fleur du Cap award-winning playwright-director Tiisetso Mashifane wa Noni presents Rise ’76: The Story of June 16th. This new play traces a community on the brink, as students, teachers and families confront the devastating implications of Afrikaans being imposed as a medium of instruction.
The play draws on real testimonies and archival material to present a fictionalised version of the truly devastating story, reimagined June 16 as a lived, intimate experience.
Cost: R150 – R250. Book now on Webtickets.
When: 8 – 30 May 2026 | From 8pm | Saturday matinee from 3pm
Where: Baxter Theatre Studio, Baxter Theatre Centre, Main Rd, Rondebosch, Cape Town
Freshlyground debuts new album live
After a five-year hiatus, the iconic South African band is back with a new album, debuting their new vocalist, Mbali Makhoba. Evolving into a new era while staying rooted in traditional African rhythms and contemporary sounds, Take Me Home is Freshlyground’s first album since 2018, featuring Makhoba’s bluesy, soulful voice.
The band is kicking off their new sound with this performance in the cultural heart of Langa, before embarking on a European tour later this month.
Cost: From R160 (early bird). Book now on Quicket.
When: Saturday, 23 May 2026 | 3pm – 5pm
Where: Guga S’thebe, Washington St, Langa, Cape Town
Norval’s Wine & Art Evening
On Thursday, 21 May, guests of Norval’s Wine & Art evening are guided through Harare-based artist Portia Zvavahera’s deeply personal Tanda rima exhibition, which showcases her dreams, experiences, and memories in dripping, dynamic visual form. Afterwards, the evening resumes with a wine tasting led by Beau Constantia’s resident winemaker, with each wine paired alongside artisanal canapés that speak to the exhibition’s themes.
In total, guests experience four premium Beau Constantia wines and four canapés, all in Norval’s Gallery 1 – a rare sighting of the museum after dark.
Cost: R500 per person, advance booking on Webtickets is essential.
When: 21 May 2026 | From 7pm
Where: Norval Foundation, 4 Steenberg Road, Tokai
Mojo Africa Day
In honour of Africa Day, Mojo Market is hosting a special, full-day celebration of the continent’s culture, rhythm, and spirit. Guests expect live local African bands, DJs, and performances all day and night, with a journey through Afrobeats, soul, jazz, house, amapiano, and everything in between. Everyone is encouraged to dress up for a chance to win a cash prize, whether it’s traditional, modern, or a fusion of the two.
Mojo Market’s usual 35+ food vendors and five extensive bars are available all day, alongside the festivities.
Cost: From R90. Book now on Quicket.
When: 23 May 2026 | 9.30am – 11am
Where: Mojo Market, 30 Regent Road, Sea Point, Cape Town
Simon’s Town Festival
This year’s edition is a more inclusive, town-wide celebration of Simon’s Town, inviting visitors and locals to explore the suburb from the mountain to the sea and everything in between. With a programme featuring everything from easygoing, intimate jazz events to fun races, the festival offers activities for people of all ages and interests.
Across the weekend, live music brings energy to the streets and venues, and participants take part in numerous activities — from beer-drinking sprints to heritage walking tours — as they explore the seaside town. The detailed programme, including the events and times for each day, can be found on the website. Festivalgoers are encouraged to support local businesses, from accommodation to shops, during their stay.
Cost: From R50. All listed activities are booked separately using the website.
When: 15 – 17 May 2026 | Various starting times
Where: Various locations across Simon’s Town
Carmen
Cape Town Opera is bringing Bizet’s Carmen, one of the world’s most loved operas, to the stage in a searing new production.
At the helm of the Cape Town Philharmonic Orchestra, conductor Tim Murray drives the score with electrifying momentum, leading a full ensemble of singers, dancers and orchestra in a production of thrilling scale and dramatic force.
With striking costumes by Maritha Visagie and a powerful set design by Greg King, Cape Town Opera’s Carmen is a visually arresting and musically charged theatrical event not to be missed.
Cost: R180 – R950. Tickets can be booked on Webtickets.
When: 19 – 31 May 2026 | 7pm | Sat and Sun at 2pm
Where: Artscape Theatre Centre, D.F. Malan St, Foreshore
Shakespeare Schools Festival
The annual Shakespeare Schools Festival, now in its 16th year, is opening at the Baxter Theatre, featuring over 40 drama groups in dynamic, abridged renditions of Shakespeare’s plays.
As Africa’s largest youth drama festival, the Shakespeare Schools Festival has worked with over 15,000 learners and 1,000 teachers since 2009. With schools from all across the Western Cape and performances of many of Shakespeare’s classics, the festival fosters literacy, self-expression, and inclusivity, welcoming blind, deaf, and physically challenged performers.
This weekend’s lineup includes performances from both Paarl Boys’ and Girls’ (Friday), and International School of Cape Town’s Twelfth Night (Friday & Saturday).
Cost: R75 – R150. Book now on Webtickets.
When: 6 – 23 May 2026 | Shows start 7pm
Where: Pam Golding Theatre, Baxter Theatre, Main Rd, Rondebosch
Cape Town Comedy Club
No longer a set venue in the V&A Waterfront, Cape Town Comedy Club now offers pop-up shows at various venues across the Mother City. Headed by veteran Kurt Schoonraad and featuring newer comic voices like Phil de Lange and Wesley Paulse, comedy fans should keep an eye on their socials to see what big event is up next.
For May, the Comedy Club is bringing a completely fresh show to a whole new venue. Award-winning legend Stuart Taylor is the main attraction, alongside the quick wit of de Lange and the smooth delivery of Paulse – all performing on one stage, at the same time.
Cost: R120. Tickets available on Quicket.
When: Next show on 28 May 2026 | From 7.30pm
Where: Bomb Shelter Brew Pub, Unit B3 Park, Sunrise Circle, Pinelands, Cape Town
Month of HER
This May, Cape Grace is dedicating the entire month to women, for mothers, daughters, and sisters alike.
Her Afternoon Tea is served every weekend in May and is curated by Amanda Strydom, Cape Grace’s Food and Beverage director. The occasion features many Heirloom Restaurant favourites, from gourmet finger sandwiches to warm scones with all the fillings.
Interested guests can pair this experience with a 60-minute Swedish massage, giving all women the opportunity to relax, restore, and reset. Fairmont Spa’s full treatment menu remains available, alongside the seasonal Autumn Harmony Ritual.
Cost: Afternoon Tea package is now sold out | R1995 per person (including spa treatment). Reservations can be made on the website.
When: Thursday through Sunday | Bookings at 2.30pm, 3pm, or 3.30pm (Afternoon Tea)
Where: Heirloom Restaurant at the Cape Grace, A Fairmont Managed Hotel, W Quay Rd, V&A Waterfront
Discover more Mother’s Day activities in Cape Town
Mommy & Me Expo
This special event is tailor-made for parents in need of baby supplies. Leading baby brands offer their products at exclusive discounts, making it easier to stock up on nice-to-haves and necessities for the winter. Whether it’s branded clothes, handwoven toys, educational children’s books, or even superhero face painting, the Expo is a must-visit for parents of all ages.
Cost: R50. Book a spot now on Webtickets.
When: 30 May 2026 | From 9am
Where: D’aria Wine Estate, M13, Tygerberg Valley Rd, Durbanville, Cape Town, 7550
Four Hands Wine Dinner at 12 Apostles
A collaboration between Bartholomeus Klip’s Head Chef, Louise Gillett, and 12 Apostles’ resident Chef, Christo Pretorius, this evening promises a 7-course tasting menu featuring flavours from around the world. Gillett’s dishes often reflect her South African and Italian heritage, while Pretorius is known for blending local flavours with classical French technique.
The experience is set in the hotel’s Azure Restaurant, an award-winning kitchen with views that overlook the Atlantic Ocean and a menu that champions local delicacies, particularly seafood.
Cost: R925 per person. Bookings can be made by contacting [email protected] or 021 437 9000.
When: 29 May 2026 | 6.30pm – 10pm
Where: The Twelve Apostles Hotel And Spa, Victoria Rd, Oudekraal (Nature Reserve), Cape Town
Jive Funny Championship
Then Jive Cape Town Funny Festival is South Africa’s oldest and foremost comedy festival, showcasing the best local stand-up comedians together with top international variety acts at the Baxter Theatre.
Alan Committee is the Master of Ceremonies for the festival, which features acts like shadow artist Matteo Fraziano, Britain’s Got Talent finalist Mike Woodhams, local comedians Jason Goliath and Robby Collins, and much more.
During the lead-up to the event, the Jive Funny Championship is held to crown the funniest comedian in Cape Town, and anyone can enter. The winner is then given their own set during the Funny Festival lineup and performs in front of a packed Baxter crowd.
Cost: R200 – R250. Tickets available on Webtickets.
When: 28 May – 21 June 2026 | From 8pm | Weekend matinees from 4pm
Where: Pam Golding Theatre, Baxter Theatre, Main Rd, Rondebosch
Mike van Graan Double Bill
This double-bill by multiple-award-winning playwright Mike van Graan brings together two contrasting solo works staged in the function room of a central Cape Town hotel.
The first piece, Helen of Troyeville, is a poetic drama receiving its first Cape Town season after premiering at the National Arts Festival in 2018. Performed by television actress Zolie Markey, best known for her role in the kykNET telenovela Arendsvlei, the work centres on Helen Jennings, a former Black Sash member in her seventies who becomes the victim of an opportunistic crime while attempting an act of goodwill. The script examines the intersections of privilege, power and poverty in post-apartheid South Africa.
The second piece, Pet-Friendly, is a stand-up commentary work performed by Ugandan-born actor Marty Kintu, a UCT-trained performer with credits including The Life and Times of Michael K directed by Lara Foot. Using pet ownership as a lens, the piece extends into broader local and global social commentary. Each work runs 55 to 60 minutes, with a 20-minute interval between them.
Cost: R165. Book now on Quicket.
When: 19 – 30 May | 7pm – 9.30pm (Tue – Fri) | 3pm – 5.30pm (Sat)
Where: Kloof St Hotel, 8 Rheede Street, Gardens, Cape Town
The Rocky Horror Show
The legendary cult musical The Rocky Horror Show, presented by Pieter Toerien Productions in association with the Luitingh Alexander Musical Theatre Academy (LAMTA), is in Cape Town. This electrifying staging by director Steven Stead promises to unleash all the wild energy, wicked humour and rock ’n’ roll rebellion that has made the show a global phenomenon for over 50 years.
The show stars an award -winning South African cast led by Craig Urbani (We Will Rock You), who reprises his role as Frank-N-Furter, with Léa Blerk (Joseph and the Amazing Technicolor Dreamcoat) as Janet, and Robert Everson (Noises Off) as Brad.
Cost: R295 – R495. Tickets available on Webtickets.
When: 7 April – 31 May 2026 | 8pm | Saturday at 3pm and 8pm | Sunday at 3pm
Where: Theatre on the Bay, Link St, Camps Bay, Cape Town
