RUNNING, FOOTBALL AND COMEDY IN CAPE TOWN IN MAY
May in Cape Town is for fast-paced football, major international running, early winter laughs and a spotlight on high-end African travel all come together.
The Mother City continues its tradition of curating a diverse, high-energy calendar that blends sport, lifestyle events, business and cultural experiences into a month that doesn’t slow down, even as the cooler season sets in.
From stadium showdowns and start lines to global conferences and comedy stages, here’s what’s lighting up Cape Town this May:
We Are Africa – A global stage for African Travel
Cape Town kicks off May by hosting We are Africa, one of the continent’s most influential travel gatherings, at DHL Stadium.
Running from 4 – 9 May, We Are Africa attracts tourism professionals, global buyers, some of the Africa’s most exceptional travel brands, and media for discussions shaping how the world experiences the continent.
Over four days delegates connect, share ideas, close deals and tell Africa’s story with intention.
They celebrates the continent’s diversity, creativity and cultural depth, while pushing for responsible tourism that protects and uplifts communities.
With more than 300 exhibitors, the focus is on meaningful engagement including from meetings to thought-provoking discussions on the future of luxury travel.
High-stakes football – Stellenbosch FC vs Orlando Pirates
Athlone Stadium will be the stage for a heavyweight clash under lights that could carry serious momentum for the Betway Premiership Championship.
The home team Stellenbosch FC faces Orlando Pirates on Tuesday 5 May 2026.
While the Sea Robbers are locked in a tense title race against Mamelodi Sundowns, the Maroon are pushing for a top eight finish.
With recent MTN 8 cup history between these sides, this isn’t just another fixture, it’s a Stellies’ quest for redemption.
The game kicks off at 19:30 with gates opening at least two hours before the start of the game.
Tickets are available through Webtickets.
A playoff push for Cape Town City FC
Cape Town City FC will aim to consolidate its position in the push for PSL Promotion-Relegation Playoffs when they meet Baroka FC at Athlone Stadium on 10 May.
Having missed out on the Motsepe Foundation Champion title, the Citizens will be looking for another avenue to gain promotion back to the Betway Premiership.
Currently in the top four, City’s final home game of the season against Baroka will be a pressure fixture and a defining moment in the season.
It’s the kind of fixture where the atmosphere matters just as much as the football. Expect the Blue and Gold Army to show up.
Kick off at Athlone Stadium is 15:00. Free match tickets are available through Webtickets or at the stadium on gameday.
A city on the move – Absa Run Your City Cape Town 10K
For its 11th edition on 10 May, the Absa Run Your City Cape Town 10k will see over 13 000 take on an iconic route with an even more famed finish location.
The race will finish on the historic Grand Parade with a backdrop of City Hall and Table Mountain.
Setting off from Woodbridge Island in Milnerton from 09:00, the race will take runners on a scenic route along the coastline in Paarden Island and into the city centre via the N1 and FW De Klerk Boulevard before finishing off on Darling Street.
The 10km route is fast, flat and is built for those chasing personal bests, those soaking up the atmosphere and an all-round good time.
Wings for Life World Run
On the same day, runners gather in Green Point for a race with a global purpose. The Wings for Life World Run is unlike any other, there’s no finish line, just a moving one, with participants running for those who can’t.
The event is a mix of community, innovation and cause-driven sport, raising funds for Spinal Cord Research.
The Wings for Life World Run, in its 12th year, has become he largest running event in 2021 with over 180 000 runners participating in one single event across the world.
In Cape Town, the runners will take on one of the most scenic routes which includes the Green Point Urban Park, the Mouille Point Lighthouse, the Sea Point Promenade among others.
Culture, craft, innovation and industry
Cape Town will once be hub for conferences and the meeting place for professionals across various industries.
The Mother City’s status as a tech and innovation hub comes into focus mid-month when it hosts Africa Tech Week on 12 and 13 May 2026 at the CTICC. The event brings together startups, investors, policymakers and industry leaders to explore how digital solutions can drive growth across the continent.
From keynote talks to startup showcases, it’s where ideas meet opportunity.
The CTICC will also host Enlit Africa, a end-to-end power and energy event, from 19 – 21 May 2026.
As Africa navigates complex energy challenges, provides a platform for real conversations and practical solutions. Expect deep dives into power, water and infrastructure — with insights from engineers, developers, financiers and policymakers working on the frontlines of the continent’s energy transition.
From 21 – 23 May, the BeerEx Africa will host the continent’s biggest beer expo and conference at the Newlands Cricket Ground.
The event brings together brewers, enthusiasts and industry leaders for a celebration of craft beer culture.
From technical talks and tastings to live demos and the prestigious African Beer Cup awards, it’s equal parts education and enjoyment with plenty of flavour along the way.
Tickets are available from Quicket.
A marathon moment for Africa – Sanlam Cape Town Marathon
Africa’s first Abbott World Marathon Majors Candidate takes the final step towards the big leagues on 24 May.
The 2026 edition of the Sanlam Cape Town Marathon will host 27 000 athletes for the 42.2 journey through the Mother City’s scenic landscape and iconic landmarks. They will start line outside the DHL Stadium, out to Newlands via Nelson Mandela Boulevard passing through Woodstock, Salt River and Mowbray before reaching the CBD and Sea Point for a finish in Green Point.
Beyond the flagship 42.2km race, the weekend (23-24 May) includes Peace Runs and trail events, giving runners of all levels a chance to experience Cape Town’s landscapes.
Successful evaluation would see Cape Town join the series of the world’s most renowned marathons, including the Boston Marathon, Berlin Marathon, Chicago Marathon, London Marathon, New York City Marathon, Tokyo Marathon and the Sydney Marathon.
This May marks a defining chapter for the Sanlam Cape Town Marathon as it continues its journey toward becoming Africa’s first Abbott World Marathon Major.
Jive Cape Town Funny Festival ends the month with a laugh
The 27th Jive Cape Town Funny Festival begins its three-week run on 28 May. With a line-up that features local and international acts, South Africa’s oldest and largest comedy festival will run until 21 June at the Baxter Theatre.
The festival blends local comedic talent with international variety acts, from stand-up and satire to illusion and musical comedy.
With Alan Committie as MC, this year’s programme includes Italian shadow artist and illusionist Matteo Fraziano, British vocal impressionist Mike Woodhams and Spanish balloon artist Dani Airhead.
Veteran funnyman Jason Goliath will make his Cape Town Funny Festival this year while Johannesburg-based Robby Collins will return for a second year.
Cape Town singer, comic and actor Emo Adams and music maestro Sean de Vries, who heads up the music department, with the Funny Festival band will bring music numbers with laughs.
Tickets are available through Webtickets.
Living Well, the African Way at The Good Life Show
Rounding out the month is a celebration of conscious living.
The Good Life Show takes place at the CTICC from 29 – 31 May 2026. It brings together food, wellness and sustainability in a vibrant, interactive setting.
The event will spotlight over 250 exhibitors showcasing plant-based foods, organic produce, sustainable fashion, and beauty products.
From chef demos and tastings to workshops and innovative products, it’s a space to explore how lifestyle choices are evolving.
Tickets are available through Quicket.
