May in Cape Town is packed with a lineup of events for all ages – from world-class theatre, opera, and comedy festivals to wine experiences in the Winelands, pop-culture events, and more.
Here is your ultimate guide to what’s on in Cape Town in May 2026:
Comic Con Cape Town
📅 30 April – 3 May 2026 📍 Cape Town International Convention Centre
Cape Town’s biggest pop culture and gaming festival spills into May with Comic Con Cape Town. Expect everything from comics, cosplay, and gaming to film activations, exclusive merchandise, and fan experiences. It’s a must for geeks, gamers, and pop culture lovers. For tickets, visit here.
Lucky Clover Market
📅 2 May 2026📍 Novalis Ubuntu Institute, Wynberg, Cape Town
Wander through a mix of thrift treasures, handmade crafts, holistic goods, and artisan deli stalls. Set in peaceful gardens, this community market comes alive with live music, food stalls, and plenty of hidden gems to discover. Entry is free.
Volunteer Wildfire Services Trail Challenge
📅 3 May 📍 Gardens Rugby Football Club
Trail running enthusiasts and outdoor adventurers are invited to lace up for a cause at the Volunteer Wildfire Services Trail Challenge. This much-anticipated event combines adrenaline with breathtaking scenery to support the dedicated volunteer firefighters who protect the Western Cape’s natural landscapes. Starting from the Gardens Rugby Football Club, participants can choose between a 10 km or 20 km route, both of which traverse the trails of Table Mountain and Devil’s Peak. Get more information here.
Private Salon – Sar la Rouge – Digital Art & Charity event
📅 8 and 9 May 2026 📍 Constantia
A private home in Constantia opens its doors for a two-day immersive digital art experience that blends contemporary art, music, and community impact. At the centre is Franco-Togolese digital artist Sar La Rouge, known for bold, expressive portraits that explore how screens shape perception and reality. The opening evening (8 May) is an intimate sunset event featuring live music, curated canapés, drinks, and art throughout the house. The family day (9 May) offers a relaxed, interactive experience with workshops, kids’ activities, and full access to the exhibition. All proceeds support The Bridge Orphanage. Tickets available via Quicket.
RISE ‘76: The Story of June 16th
📅 8-30 May📍 Baxter Theatre Centre
Commissioned by The Market Theatre and The Baxter Theatre to mark the 50th anniversary of the 1976 Youth Uprisings, Rise ’76: The Story of June 16th is a powerful new South African work of historical fiction by Tiisetso Mashifane wa Noni, a two-time Fleur du Cap Award-winning playwright-director.
Set in the fictional Molefe Secondary School in Soweto, the play unfolds over a single school day as students, teachers, and families confront the impact of the imposition of Afrikaans as a medium of instruction. What begins as an ordinary morning gradually builds towards a moment that will change the course of history. Get your tickets via Webtickets.
The Cableway Charity Challenge
Candlelight: Tribute to Brenda Fassie
📅 9 May 2026 📍 Hugo Lambrechts Music Centre, Cape Town
Candlelight Concerts’ special edition pays tribute to the legendary Brenda Fassie, celebrating her music through a powerful live performance bathed in candlelight. Audiences can expect a 60-minute concert featuring reimagined renditions of some of her most iconic songs, including Vuli Ndlela, Weekend Special, Too Late for Mama, Nomakanjani, and more. Tickets are available via Fever.
Nina Simone Tribute Dinner with Auriol Hays
📅 9 May2026. 📍 Time Out Market Cape Town
Step into an evening with Auriol Hays as she channels the spirit and music of Nina Simone. Through song and storytelling, Hays brings Simone’s legacy to life, capturing the power and vulnerability behind the icon. For ticket prices and information, visit here.
Musgrave Gin Floral Workshop and High Tea
📅 9 May 2026 📍 Constantia Valley
Hosted by Musgrave Gin in collaboration with uBlom, this exclusive event is elevated by a curated high tea by acclaimed chef Elsa van der Nest. Guests will create their own striking bouquet while enjoying refreshing pours of Musgrave Pink Gin or the non-alcoholic Musgrave Inspirit 0%. Afterwards, sample a high tea menu featuring buttery French sablés, finger sandwiches, a flourless chocolate cake with ganache, and a baked goat’s cheese quiche. For ticket prices, visit here.
Absa Run Your City Cape Town 10KM
📅 10 May 2026 📍 Woodbridge Island, Milnerton
This high-energy road race combines fitness with sightseeing as runners follow a scenic coastal route into the city centre. Even spectators can enjoy live entertainment and a vibrant race-day atmosphere. It’s a ‘proudly South African, proudly Cape Town’ must-experience mass-participation road-running event. Catch our Cape Town Tourism mobile team at the event and enjoy an immersive VR experience of the city. More information here.
The Human League
📅 12 May 2026 📍 Grand Arena, GrandWest Casino and Entertainment World
British synth-pop pioneers The Human League are set to deliver an electrifying night of pure 80s nostalgia, performing a string of timeless hits, including “Don’t You Want Me”, “Human”, “Together in Electric Dreams”, “Mirror Man” and “(Keep Feeling) Fascination.” Joining them as special guests are fellow UK synth-pop favourites Blancmange, whose cult classics “Living on the Ceiling”, “Blind Vision” and “Don’t Tell Me” have earned them a loyal global following. Tickets are on sale here.
Winemaker’s Dinner at Mont Rochelle
📅 15 May 2026📍 Franschhoek
Wine and food in one of the Cape’s most stunning locations? Yes, please! Begin the evening with a guided cellar tour led by winemaker Michael Langenhoven, offering insight into the winemaking process and varietals. Afterwards, tuck into a five-course menu created in collaboration with Executive Chef Terence Morris, with each dish thoughtfully matched to complement the wines and elevate every course. Tickets cost R1350. Email reception@montrochelle.virgin.com
Franschhoek Literary Festival
📅 15 – 17 May 2026📍 Franschhoek
A must for book lovers, this festival brings together leading authors, thinkers, and creatives for talks, debates, and intimate discussions, all set in Franschhoek. The Franschhoek Literary Festival, launched in 2007, takes place annually on the third weekend of May. Tickets from around R125 via the festival website.
Carmen
📅 19 – 31 May 2026 📍 Artscape Theatre Centre, Cape Town
Cape Town Opera presents a bold new staging of Carmen, Georges Bizet’s timeless opera. Set against a backdrop of jealousy and desire, the story follows the fiery, independent Carmen as she defies convention and captivates all who cross her path, ultimately setting tragedy in motion. Tickets are available via Webtickets.
Sanlam Cape Town Marathon
📅 23 – 24 May 2026 📍 Cape Town
One of Africa’s premier running events, the Cape Town Marathon draws elite athletes and casual runners from around the world. Renowned for its scenic yet fast route, the race is a highlight of the global marathon calendar. More information here.
A Night of Wine & Wonder
📅 23 May 📍 Protea Hotel Stellenbosch and Conference Centre
Set in the heart of one of South Africa’s most striking wine regions, this curated experience brings together 17 top wine farms, great music, and plenty of space to relax and socialise. It makes for the perfect night of sipping and discovering your next favourite wine. Get your tickets via Quicket.
ACDC Duet Xchange 2026: The Art of the Duet
📅 22 – 23 May 2026 📍 Star Theatre, Homecoming Centre
This two-night contemporary dance platform is presented by Anderson Carvalho Dance & Choreography. This artist-led platform is dedicated to duet-based collaboration, bringing together local and international artists to create new choreographic works rooted in dialogue and shared authorship. Guest choreographers and companies featured include New World Dance Theatre, Northern Dance Academy, and Janine Booysens. For more information and tickets, visit here.
Jive Cape Town Funny Festival
📅 28 May – 21 June 2026 📍 Baxter Theatre Centre
The Jive Cape Town Funny Festival has been the Mother City’s ultimate cure for chilly winter evenings for more than two decades. Since its debut in 1997, the festival has consistently drawn sold-out crowds. This year’s edition promises a laugh-a-minute experience, featuring a stellar international and local line-up. Audiences can look forward to the mesmerising Italian shadow artist and illusionist Matteo Fraziano, the UK’s dynamic singing impersonator Mike Woodhams, the wildly inventive Spanish balloon artist Dani Airhead, and some of South Africa’s finest comedic talent, including Jason Goliath and Robby Collins. Get your tickets here.
The Good Life Show
📅 29 – 31 May 2026 📍 Cape Town International Convention Centre
The Good Life Show celebrates conscious living, food innovation, wellness, and sustainable lifestyle inspiration under one roof. Over three days, visitors can explore a curated mix of plant-based cuisine, health and wellness brands, eco-friendly products, and live cooking demonstrations from top chefs and industry experts. Tickets start at R150 and are available via Quicket.
Bed By 10pm LGBTQIA+ Edition
📅 30 May 2026 📍 The District, Harrington Street
Want to serve face, dance like it’s the early 2000s, and still be tucked up in bed by 10 (ish)? Bed By 10: LGBTQIA+ Edition is your throwback party for legends who love a big night out but love a good night’s sleep even more. Expect nonstop 80s–00s anthems, iconic drag performances, and live acts, DJ sets. Get your tickets via Howler.
Amapiano Fest Cape Town
📅 30 May 2026 📍 Cape Town High School, Gardens
Amapiano Fest is a major South African outdoor music festival and cultural celebration dedicated to the Amapiano genre, featuring top DJs, producers, and live performances. Book your tickets via Howler.
Sunday Lunch at Connexxion Restaurant
📅 31 May 📍 Garden Court Victoria Junction
Garden Court Victoria Junction hosts a Sunday lunch buffet on the last Sunday of each month. Enjoy a generous selection of fresh salads, artisanal breads, hearty hot dishes such as lamb, chicken, and curry, and classic desserts. Priced at R375 per person, R185 per child under 12, and children under 4 eat for free. For more information, email gcvictoriajunction.reservations@southernsun.com
