Spring is in full swing, and October is full of exciting events taking place across the Mother City. From music festivals and garden celebrations, to wine tastings and Halloween parties, there’s something for everyone in Cape Town this month.
In The City with Isaiah Rashad & Sinéad Harnett
The American rapper and singer, known for chart-topping tracks like Headshots, Free Lunch, and Wat’s Wrong (feat. Zacari & Kendrick Lamar), is making his long-awaited African debut later this year, headlining In The City after Rocking the Daisies was cancelled.
With dreamy production that blends rap and contemporary R&B, and introspective lyricism that resonates with audiences around the world, Rashad has remained an influential figure in hip hop despite his long absences between albums. His most recent work, It’s Been Awful, was released to critical acclaim in 2026, with songs like Cameras (feat. Dominic Fike) and Boy in Red (feat. SZA).
Performing alongside Isaiah Rashad at In The City, Sinéad Harnett is a Thai-Irish R&B singer-songwriter who brings her soulful voice to a mix of upbeat electronic dance tracks and slower, jazzy ballads. She rose to prominence with her 2014 single No Other Way, before releasing her biggest song, If You Let Me, which has reached over 100 million streams on Spotify.
The full In The City lineup includes Rashad and Harnett alongside a mix of local DJ’s and artists: Kay Faith, Mila, Nice Nice, Enrico Celento, Dboy, Kdollahz, Shakes, Smoolana B2B Sifiso, Jaykatana, and Fish Parcel B2B Cuito.
Cost: From R599 per person. Book now on Quicket.
When: Saturday, 3 October 2026 | 12pm – 11pm
Where: The Ostrich (Ostrich Ranch), Van Schoorsdrif Rd, Philadelphia, Cape Town
Toyota Stellenbosch Woordfees 2026
As spring takes shape over the Cape Winelands in early October, the historic town of Stellenbosch transforms into a hub of culture and art with the Toyota Stellenbosch Woordfees. For nine days, the festival brings together world-class music, theatre, dance, literature, visual art, food, wine, conversations, and outdoor experiences in one town-wide celebration.
One of the biggest highlights at Woordfees is the Toyota Music Festival at the Jan Marais Park. Here, some of South Africa’s most popular artists perform live under the night sky, as fans watch on with blankets, food, and friends.
This year’s line-up includes chart-toppers and crowd favourites from various genres, such as Jeremy Loops, Spoegwolf, Booshle G, and the powerhouse duo of Zaan Sonnekus and Tasché. Adding to the excitement is the festival debut of internationally acclaimed singer-songwriter Vusi Mahlasela, “The Voice of South Africa”. Joined by his protégé Tsholofelo Papo, Mahlasela will perform the songs that have inspired audiences across the globe with messages of hope, reconciliation, and humanity – such as Silang Mabele and Weeping.
Food and wine enthusiasts are similarly well catered for at Woordfees. Festival favourites such as the Long Table and Street Soirée return, inviting guests to enjoy memorable meals beneath Stellenbosch’s famous oak trees. These sought-after experiences combine fresh food, premium local wines, and the unique atmosphere of one of South Africa’s most scenic towns.
Once again, Toyota Stellenbosch Woordfees and Strauss & Co. are putting together an auction of beautiful, exciting and challenging contemporary art, giving the public an opportunity to buy works by some of the foremost artists working today. A selection of works available at auction will be exhibited in the Stellenbosch Town Hall. Klein Wêreld, an exhibition of small works by contemporary artists, and Spier’s Creative Blocks present further opportunities to purchase art at very affordable prices.
The festival’s theatre programme remains one of its strongest offerings, featuring acclaimed productions, celebrated performers, and some of South Africa’s leading directors.
With hundreds of events spread across nine days, the Toyota Stellenbosch Woordfees offers something for every taste and every generation – from open-air concerts and award-winning theatre to fine food, thought-provoking discussions, family activities, and unforgettable cultural experiences. More information is available on the website.
Cost: Various prices. Tickets are available on Quicket.
When: 3 – 11 October 2026
Where: 37 Ryneveld St, Stellenbosch
Expression: Rhythm to Runway
The Fusion Project’s 2026 annual showcase, Expression: From Rhythm to Runway, stages fashion as live performance, built around the relationship between music and couture. The event is an initiative of Charlene Sauerman Couture, with the Fusion Project’s design students translating personal heritage and cultural influence into original couture pieces for the runway.
Performers from Kwena Music, including Metrovilla, Faker Streets and Ruben Gerritz, share the stage with the designs, creating a live dialogue between sound and garment rather than a conventional silent runway walk. South African couturier Jacques Lagrange makes a guest appearance as part of the programme, adding an established industry name alongside the student designers.
The format positions the show as multi-sensory rather than a straightforward fashion parade, with music, movement and design conceived together rather than added as a soundtrack to a finished collection.
Cost: From R280 per person. Book now on Quicket.
When: 2 & 3 October 2026 | 7.30pm – 10pm
Where: Kwena Studios, 191 Sunningdale Drive, Sunningdale, Cape Town
Keanan Eksteen Live
Rock musician Keanan Eksteen brings his band to Café Roux, performing songs from his new album alongside established crowd favourites. Eksteen, who grew up in Kraaifontein, built his sound on a childhood soundtrack of The Beatles, Fleetwood Mac and Tom Petty, blending classic and modern rock influences into a style distinctly his own.
The show follows the June release of his second full-length album, Starring, released on vinyl as a mix of previously released singles and new material. The genre is rock and roll, delivered with the energetic stage presence that has built Eksteen’s following both locally and across Europe.
The performance falls ahead of the band’s fifth European tour, where they’ll play festivals in Germany and the Netherlands, and shortly before Eksteen performs at Ellis Park Stadium for a Springbok versus All Blacks match. Café Roux operates a seated table format, with tables booked under the same email address grouped together.
Cost: R200 per person. Book now on Quicket.
When: 2 October 2026 | 6pm – 9.30pm
Where: Café Roux, Chapman’s Peak Drive, Noordhoek, Cape Town
VarieTease
BB Productions ZA brings its VarieTease show to Greenhaus, combining burlesque, live singing and drag performance into a single variety night. The production is built around audience participation, elaborate costuming and comedic segments, positioning itself as a celebration of self-expression rather than a straightforward cabaret.
The show draws on classic burlesque tradition, emphasising style and reveal-and-conceal performance over overt sexuality, in line with the genre’s modern presentation. Tickets are limited to 70, with seating automatically allocated by table through the Quicket booking system, and larger groups of nine or more may be split across multiple tables.
The event carries an LGBTQ+ inclusive framing throughout its promotion, and attendees are encouraged to dress to impress for a chance to win prizes on the night.
Cost: R200 per person. Book now via Quicket.
When: 2 October 2026 | 8pm – 10pm
Where: Greenhaus, 14 Leadville Way, Sunningdale, Cape Town
Franschhoek Classic Car Festival
The Franschhoek Classic Car Festival returns to the Huguenot Monument for its third edition, marking a follow-up to last year’s sell-out weekend. The festival was founded by classic car enthusiasts Graham Warsop and Theo Lötter, with Lötter serving as CEO and Warsop as Chairman.
The signature Forty of the Finest display returns across both days, showcasing forty pre-1995 vehicles representing forty different marques. The 2026 edition also marks 75 years of Formula One with a championship-winning F1 car on display, alongside a tribute to F1 champions through the decades, including South African driver representation. Additional curated displays include a Ford Perana tribute and anniversary showcases for MG and BMW, alongside Mercedes-Benz and Golf GTI anniversary displays. Vespa and Land Rover exhibits also feature, with some displays running for one day only.
Both days include parades of classic and supercars along the main road, Huguenot Street. Visitors also have access to Franschhoek’s restaurants, boutiques, galleries and the Village Market during the festival.
Cost: R250 per person (one-day access) | R400 (weekend pass) | Free for u18s accompanied by adult
When: Saturday & Sunday, 3 & 4 October 2026 | From 10am
Where: Franschhoek Huguenot Memorial Monument, 13 Lambrechts Rd, Franschhoek
Siya Seya: Traveling Man
Multi-award-winning comedian Siya Seya brings his new stand-up show, Traveling Man, to the Homecoming Centre. The show is built around Seya’s travels across other African countries, woven together with reflections that move back and forth through his own past experiences.
Rather than a single-theme set, the show uses travel, both physical and through memory, as a structural device for the evening’s material, giving the performance a narrative throughline alongside individual comic bits.
The show carries an age restriction of no under-16s, in keeping with typical stand-up content.
Cost: R200 per person. Book now on Quicket.
When: 2 October 2026 | 7.30pm – 10pm
Where: Homecoming Centre, 15 Buitenkant Street, District Six, Cape Town
Elysium
Cape Ballet Africa (CBA) is set to captivate audiences with ELYSIUM, a new quadruple bill at The Baxter this October, launching the dynamic company’s exciting Spring Season.
Hot off its highly successful run of Swan Lake in Johannesburg, CBA presents ELYSIUM at The Pam Golding Theatre at The Baxter from 3 to 10 October. The ballet brings together four exquisite and diverse ballets by celebrated choreographers George Balanchine, Nacho Duato, Kenneth Tindall and Michelle Reid, each offering a unique perspective on the human experience.
Through contrasting choreography, music, and artistic styles, ELYSIUM creates a rich, inspiring ballet experience that explores themes of love, resilience, transformation, and joy through the range, beauty, and emotional depth of ballet.
This captivating new production brings together works from some of the world’s most celebrated choreographers, brought to life by Cape Ballet Africa’s award-winning dancers. Elysium plays at the Baxter for one week only, with two weekend matinees and one Seniors Special Performance during the week.
Cost: R200 – R495 per person. Book now on Webtickets or via Pick ‘n Pay stores nationwide.
When: 3 – 10 October 2026 | From 7.30pm | From 3pm (weekend matinee) | From 11am (Seniors Special Performance)
Where: Baxter Theatre Centre (Pam Golding Theatre), Main Rd, Rondebosch, Cape Town
Sunset Sweatshop, Freddy L & Sossi Live
Three South African acts share the stage at Woodstock Brewery for a night spanning several genres. Headliners Sunset Sweatshop play a genre blend of goema rock, reggae, folk and funk, drawing on infectious, festival-oriented songwriting that has built them a strong following on the local live circuit.
Alternative indie trio Freddy L brings soaring melodies and direct songwriting to the middle of the bill, while Johannesburg act Sossi closes out the lineup with emotionally driven pop built on catchy hooks and storytelling-led lyrics. Genre spans rock, reggae, folk, funk, indie and pop across the three acts.
Cost: R200 per person. Book now on Quicket.
When: 2 October 2026 | 8pm – 11.30pm
Where: Woodstock Brewery, 252 Albert Road, Woodstock, Cape Town
Mommy & Me Expo
The Mommy & Me Expo returns to D’aria Wine Estate for a two-day pregnancy, baby and toddler market, bringing together more than 60 exhibitors selling clothing, nursery furniture, educational toys and maternity essentials.
The expo covers each stage from bump to toddler, with sections spanning maternity fashion and breastfeeding products through to prams, bedding and decor for the nursery. Both local and international baby brands take part, offering products at discounted expo pricing not typically available in retail.
Beyond shopping, the event has previously included giveaways and competitions promoted through the organiser’s social channels in the lead-up to the expo, giving attendees additional reasons to visit across the full two-day run.
Children under 12 enter free, making the event accessible for families attending with older siblings alongside a new baby or toddler.
Cost: R100 per person. Book now on Webtickets.
When: 3 & 4 October 2026 | 9am – 3pm
Where: D’aria Wine Estate, M13, Tygerberg Valley Road, Durbanville, Cape Town
Story Jam
KAYA’s latest outing, Story Jam, invites everyone to the stage to share their funniest, messiest, most embarrassing, and honest stories in front of a live audience. No notes, no script, just the truth.
With social media making so much of our day-to-day communication happen through a phone screen, Story Jam gives us all a chance to build real, tangible connections with strangers without it feeling awkward or forced. In a city that can feel as isolating as Cape Town often does, it’s a great way to meet new people, hear their stories, and say something you’ve been meaning to get off your chest.
Each teller gets five minutes to share their personal anecdote while staying on the night’s theme. Stories can be hilarious, heartwarming, or heartbreaking; the atmosphere is meant to make everyone feel welcome saying what they have to say. Eight participants take the stage every week with just their voice, their memory, and their honesty.
Sessions happen with a new theme every Tuesday, and sign-up is completely free. With a warm and inviting atmosphere at KAYA HQ that’s open to all kinds of entertaining and difficult stories, no matter the subject matter.
Cost: Tickets start from R93 per person (early bird). Book now on Fixr.
When: Tuesdays | 6.30pm for 7pm – 9pm
Where: KAYA HQ, 35 Loop St, Cape Town City Centre
Unexpected Pairings at ROOI
ROOI’s latest private dining event, Unexpected Pairings, sees guests indulge in five curated set courses, each paired with a slightly unusual wine companion meant to intrigue and leave taste buds craving more. Unlike a more traditional wine-pairing experience, the flavours collide, contrasts become more apparent, and different tastes work together in unlikely ways.
The set menu includes a first course of tuna on toast, followed by aged beef with quail egg, a sea bass dish, salted coconut alongside chocolate strawberries, and cheese & jam to complete the experience. For a unique dining experience at one of Cape Town’s most exclusive restaurants, make sure to book a table for October’s edition.
Cost: R1850 per person. Book now by contacting [email protected] or 021 431 5888.
When: 2 October 2026 | Seatings from 6.30pm – 9pm
Where: ROOI, One & Only Cape Town, Dock Rd, Victoria & Alfred Waterfront, Cape Town
Framed Sessions
This multi-disciplinary, multi-creative arts experience spans photography, live music, painting, and dynamic projection, highlighting many up-and-coming Cape Town artists and their work.
The event opens with a photography exhibition focused on local musicians, featuring stills from seven photographers who regularly document the Mother City’s live music scene. The free walkabout includes a live DJ vinyl set from Waxx Garden. The featured artists include Hanno van Vuren, Brig Stanford, Emma Snyman, Frame The Gig, Vuyo Polson, Rishi Prag, and Warren Talmarkes.
The evening continues with a cross-industry improv session, where musicians, painters, sketchers, and a projectionist collaborate on a piece that evolves with each artist’s input.
Finally, the event concludes with a live show featuring alternative Afrikaans band Dierbaar, multi-genre Afrojazz group Operation Khataza, and indie-rock outfit Toughguy. The night culminates in a fully collaborative finale where each band performs the same song together, drawing on influences from across Cape Town’s vast soundscape. Those interested can join the official event after-party at Surfa Rosa.
Framed Sessions highlights the inherent collaboration and community spirit within South African art, inviting guests to experience creative works from artists across various mediums and learn how they intersect and support one another. Each participating photographer will have multiple prints available for purchase after the show, and anyone interested can contact Framed Sessions directly for more information.
Cost: From R200 per person. Book now on Quicket.
When: 3 October 2026 | 4pm – 10pm
Where: The Pink Room @ Gorgeous George Hotel, 118 St Georges Mall, Cape Town City Centre
Digger
Directed by the Oscar-winning visionary Alejandro G. Iñárritu, best known for Birdman and The Revenant, this latest film is a comedy of “catastrophic proportions” starring Tom Cruise. Beyond that, we don’t know much.
The most powerful man in the world races to prove he is humanity’s saviour before the disaster he unleashed destroys everything.
The cast is filled with some fan favourites, including Jesse Plemons, Sandra Hüller, Riz Ahmed, John Goodman, and Emma D’Arcy. The movie’s very strange and intriguing “teaser trailer” (which, for some reason, features clips from most of Cruise’s previous films) is out now on YouTube.
When: Opens in theatres on 2 October 2026
Where to watch: Set for release at Ster-Kinekor cinemas nationwide
Kinnes van Somers
Kinnes van Somers arrives at the Baxter Studio as the second Finest of the Fest winner from the 2026 Zabalaza Theatre Festival, reworking the Afrikaans folk legend of Antjie Somers, a shape-shifting figure said to walk between light and lie in the shadows of a small community. The production is devised and performed by an ensemble of five, including co-director Tamsyn Alexander, who collectively bring Antjie and the story’s other characters to life.
Directed by Tamsyn Alexander and Hanro Cloete, the piece draws on childhood warnings, whispered kitchen questions and inherited fear, tracing how a bedtime cautionary tale can blur into something a child grows to embody. The work leans on folk drama and shadow play, staged with props including enamel kitchenware and cobalt blue overalls tied to the character’s traditional image.
Sylvaine Strike, credited as mentor and creative supervisor on the production, also oversees the companion Finest of the Fest winner, Until I Arrive, running the week before in the same venue.
Cost: R80 – R120 per person. Book now via Webtickets.
When: 6 – 10 October 2026 | From 8pm | 2pm (Sat matinee)
Where: Baxter Studio, Baxter Theatre Centre, Main Road, Rondebosch, Cape Town
Dave
History-making British rapper, producer, and songwriter Dave brings his critically acclaimed The Boy Who Played the Harp Tour to South Africa this October.
At just 27 years old, Dave’s impact on the music industry is undeniable, with tracks such as Location and Sprinter solidifying his star power in the UK rap game. He recently made history as the first and only UK rap artist to debut three consecutive studio albums at number one on the UK Albums Chart.
In 2025, the star collaborated with another global icon, Tems, to create the smash hit Raindance. The track debuted at number five on the UK singles chart, peaking at number one and remaining in the top 40 for 17 weeks. In addition to Tems, Dave has worked and collaborated with Central Cee, Burna Boy, Giggs, Stormzy, James Blake, AJ Tracey and more.
Cost: From R685 per person (Standing Ticket). Buy tickets on Ticketmaster.
When: Tuesday, 6 October 2026 | From 8pm
Where: GrandWest Grand Arena, 1 Jakes Gerwel Dr, Acacia Park, Cape Town
The Social Reckoning
The much-anticipated sequel to the Facebook origin story The Social Network follows the true story of Facebook engineer Frances Haugen (Mikey Madison), who blows the whistle on the trillion-dollar corporation’s darker secrets. The cast also includes Jeremy Allen White as a Wall Street Journal reporter and an older Mark Zuckerberg, now played by Jeremy Strong.
Aaron Sorkin, the writer of the original film (which won three Academy Awards), returns as the film’s writer-director. After The Social Network uncovered many of the scandals that plagued Facebook’s formative years, The Social Reckoning dives even deeper into the terrifying true story of what the company has become over the years.
The film’s trailer is out now on YouTube.
When: Opens in theatres on 9 October 2026
Where to watch: Likely for release at Ster-Kinekor cinemas nationwide
The South African Pride Ball
Exactly 36 years after the first Pride march in South Africa, Edition Events and the Royal House of La’Beija RSA are honouring the queer icons and activists who made the country what it is today. The celebration takes the form of a classic queer ball, with multiple categories for contestants who want to put their stamp on the competition.
Each award commemorates a queer South African legend, from Granny Lee to Simon Nkoli and much more. Whether it’s a fashion look, the best pro-LGBTQ poster, or a live showcase, there are many ways to win the crowd’s hearts and take home a prize.
Doors are open to everyone: queer people, femme-presenting individuals, straight allies, and anyone else who wants to walk for a category, cheer from the sidelines, or even just dance the night away. Any queries can be directed to [email protected].
Cost: R150 per person | R500 for five (group ticket). Book now on Quicket.
When: Saturday, 10 October 2026 | 8.30pm – 2am
Where: Hearty @ The Old Biscuit Mill, 375 Albert Rd, Woodstock, Cape Town
World Homeless Day Run
Raising awareness for the housing crisis and the rampant homelessness in Cape Town and worldwide, this run honours World Homeless Day with a 5km run (or walk) around the Rondebosch Common. Funds raised support U-TURN Homeless Ministries and its programmes that support homeless citizens with basic needs, rehabilitation, skills training, and work opportunities.
Participants can pay for an official U-TURN green tee, or join the run for free while wearing their own green T-shirt. Those wanting their runs officially timed must register with Parkrun separately.
Cost: Free | R120 for U-TURN tee. Book now on Quicket.
When: Saturday, 10 October 2026 | 7am – 10am
Where: Rondebosch Common, Park Rd, Rondebosch, Cape Town
Voices of the Ages: Internet Athi, Zolani Mahola, Louis Mhlanga
Three of South Africa’s biggest voices come together for a curated concert series this October. Presented by Elvis Sibeko Studios at the Artscape, the live shows let audiences experience artists who have helped define many of Mzansi’s beloved genres through rich storytelling and rhythmic instrumentation.
The first of three concerts is Louis Mhlanga, often called one of Africa’s great guitarists. With a show rooted in African jazz tunes and a mix of traditional sounds and fresh arrangements, Mhlanga brings audiences deeper into his award-winning discography, including work alongside Miriam Makeba, Hugh Masekela, and Busi Mhlongo.
The second show is headlined by the most exciting name in South African jazz, Internet Athi. The singer was listed as Apple Music’s latest Up Next SA Artist, and his 2026 album Polymorphism has received widespread critical acclaim and over a million streams on Spotify. Listeners can expect reimagined versions of fan favourites like his 2024 hit Wena, as well as renditions of album tracks, including Nguwe, Mna, and Undithembisile.
The third and final concert is all about Zolani Mahola’s new album People Power. It’s the latest work from the ex-Freshlyground singer and one of Mzansi’s most recognisable voices, blending Afro-pop, African soul, Gqom, and acoustic singer-songwriter ballads. Backed by her all-female band, The Feminine Force, Mahola continues her creative vision of creating community and inspiring hope through song.
Cost: R350 – R650 per person. Book now for Louis Mhlanga, Internet Athi, and Zolani Mahola via Webtickets.
When: Thursday – Saturday, 8 – 10 October 2026 | 8pm – 9.10pm
Where: Artscape Theatre Centre, D.F. Malan St, Foreshore, Cape Town City Centre
Open Studios
This October, the Deep South once again becomes a walking art festival as Open Studios Fish Hoek & Clovelly returns for one weekend only.
After a successful launch last year, 20 locations across the two coastal suburbs invite the public to view the work of over 30 local artists, from painting and printmaking to ceramics, sculpture, and mixed media.
Collectors and enthusiasts are welcome to join the ticketed preview event, where curious professionals get a sneak peek at the exciting artworks on display before the event is opened to the public. The preview takes place at the family-run department store AP Jones and includes live performances, a bespoke installation, a complimentary coffee voucher, a wearable badge, and a glass of Lubanzi wine.
From Saturday, Open Studios gives the public a chance to view inspiring artworks throughout the morning and afternoon and even buy them directly from the artists. Interactive activities are also available, including a DIY Post-it note exhibition that everyone is invited to contribute to. Finally, featured artists were challenged to design an exciting eco-friendly wine container, and visitors are encouraged to vote for their favourites, with prizes for both the public and the winning concept.
Full artist profiles are available on the website, along with a detailed map, route guide, and event updates.
Cost: Free (public viewing) | R150 per person (preview event). Book now on Quicket. Tickets are not needed for the open exhibitions during the weekend.
When: Friday – Sunday, 9 – 11 October 2026 | 10am – 4pm | From 9.30am (preview)
Where: AP Jones, 98 Main Rd, Fish Hoek, Cape Town (preview) | The full map of participating studios can be found online.
B-Side
For vinyl lovers, B-Side is an intergenerational house music party that honours the disco, jazz, soul, and funk influences that make the genre what it is. A joint collaboration between For The Record SA and Rotation CPT, it’s an event where the music comes first, creating an all-inclusive space for Cape Town’s audiophiles, collectors, curators, producers, and selectors.
The lineup includes Leighton Moody b2b Cassiem Latief, BCM b2b Hypoestes, DJ Real Rozzano, Justin Slack, and Neil Gain b2b Irshaad Sanmaai.
Cost: R150 per person. Book now on Quicket.
When: Saturday, 10 October 2026 | 2pm – 2am
Where: Natural Mystic, 92 Station Rd, Observatory, Cape Town
Cape Town Craft Club
The Cape Town Craft Club circle brings creative people in the city together to make stuff in a laid-back, fun, judgement-free space. Everyone is welcome, from seasoned makers to absolute beginners.
Attendees are encouraged to bring their embroidery kit, clay toolbox, Copic markers, sewing machine, or whatever creative project they’re working on, and to join the club at Bree Street Community Hall. Craft circles are hosted by Andie Reeves, teacher, textile artist, and founder of Cape Town Craft Club.
Craft Club is an ideal activity for individuals and friend groups who want to meet like-minded people who make stuff, commit to making time for creativity, need guidance or input on a creative project, would like to work among those who inspire them, or simply crave a creative outlet. Details for club meetings are on Instagram.
Cost: R150 per person. Tickets can be bought on Quicket.
When: Thursday, 15 October 2026 | 6pm – 9pm
Where: Bree Street Community Hall (behind Clarke’s), 133 Bree St, Cape Town City Centre
Nelson Mandela Marathon
The inaugural Nelson Mandela Marathon brings 20,000 runners and walkers through a 42km route across Cape Town in honour of Nelson Mandela’s enduring legacy.
Organised by international sports company Golazo in partnership with the Nelson Mandela Foundation, the event donates all profits directly to the Foundation, which was established by Mandela after his retirement from public life to advance justice, dignity, equality and freedom through programmes in education, rural development and HIV/AIDS.
The marathon route begins on Strand Street and passes through the Atlantic seaboard, the Foreshore, and Milnerton before finishing on the historic Grand Parade, with Robben Island visible on the horizon. Final route details will be confirmed at the end of June 2026. Four ambassadors have been named: Dr Paul Tergat, five-time World Cross Country Champion and IOC member; Catherine Ndereba, two-time World Marathon Champion and four-time Boston Marathon champion; Hendrick Ramaala, former New York City Marathon champion; and Prudence Sekgodiso, women’s 800m world champion at the 2025 World Athletics Indoor Championships.
Joining the weekend is the Slave Route Challenge, a historically significant Cape Town race established in 2011 by Itheko Sport Athletic Club, offered in 21km, 10km, and 5km distances. The Slave Route Challenge routes pass landmarks including the Castle of Good Hope, Company’s Garden, Bo-Kaap, and District Six.
Cost: R700 (42km) | R260 (21km) | R190 (10km Run) | R150 (10km Walk) | R80 (5km). Entries open on the website.
When: 18 October 2026
Where: Strand Street, Cape Town | Finish: Grand Parade, Cape Town
The Cape Orchid Spring Show
Join the Cape Orchid Society for an extraordinary weekend to celebrate the season of new beginnings at the Spring Splendour Orchid Show. Set against the iconic silhouette of Devil’s Peak, this floral showcase in the ‘burbs promises breathtaking orchids, friendly experts, and a social day of connecting over fragrant flowers.
The Cape Orchid Society Spring Show is one of the society’s two flagship annual events that celebrate orchids in all their glory. For one special weekend only, society members and private growers display their finest orchids, offering visitors a rare chance to see these extraordinary flowers up close.
A wide variety of orchids and gardening supplies are available for purchase at the show, allowing anyone to start their very own orchid garden. Many expert vendors are on hand to sell orchids and companion plants, offer trusted advice, and provide everything needed to keep these new treasures thriving at home. The R20 raffle is also not to be missed, giving one lucky winner a collection of high-quality, vibrant orchids.
Cost: Free entrance
When: Saturday & Sunday, 17 & 18 October 2026 | 9am – 4pm (Saturday) | 9am – 3pm (Sunday)
Where: 6th Rondebosch Scout Group Hall, Chess Road, Rondebosch (The venue is wheelchair accessible)
Ne-Yo
As part of his globe-trotting Nights Like This 2026 tour, three-time Grammy award-winning hitmaker Ne-Yo makes a highly anticipated stop in the Mother City.
Ne-Yo’s illustrious music catalogue includes a collection of global hits that every South African should know, including So Sick, Miss Independent and his collaborations with pop legend Pitbull: Give Me Everything and Time of Our Lives.
Over the span of his career, Ne-Yo has generated a combined total of 23 billion streams worldwide and a strong South African fan base that is in for the show of a lifetime this October.
Cost: From R990 per person. Book now on Webtickets.
When: Friday, 17 October 2026 | From 6pm
Where: GrandWest Grand Arena, 1 Jakes Gerwel Dr, Acacia Park, Cape Town
Junior Chef Fiesta Cooking Class
François Ferreira Academy hosts a hands-on children’s cooking class built around a Mexican-inspired menu, held in the school’s professional teaching kitchen on the Garden Route. Participants prepare their own Big Mac burritos and apple and cinnamon empanadas under the guidance of the academy’s chefs, working through each recipe from start to finish.
François Ferreira Academy is an accredited culinary arts and hospitality training institute, established in 2004 and based at Mount View Resort in George. Its kids’ cooking classes give younger learners exposure to a working chef training kitchen normally used for the academy’s professional diploma and certificate courses.
The class runs as a single morning session with limited seating, positioned as a hands-on activity rather than a demonstration-only format, with children actively involved in each stage of preparation.
Cost: R480 | Booking available on Quicket.
When: 17 October 2026 | 9am to 12pm
Where: François Ferreira Academy, Farm 208, R102 Airport Road, George
Don Giovanni
Opera UCT and the Cape Town Philharmonic Orchestra, two of the Mother City’s most celebrated classical companies, unite for one week this October, bringing Mozart’s Don Giovanni to life at the Baxter.
Created by Mozart and his librettist, Lorenzo Da Ponte, the two-act opera is based on an old Spanish legend of a man who devotes his life to seducing women, and the consequences of his actions. The narrative questions the main character’s identity, looking beyond the legend and asking who he truly is, why he does it, and what he fears. The score encapsulates this inner conflict, combining tense orchestral writing, expressive arias and lively ensembles into one tense character piece.
Far from a local-only production, the crew includes several acclaimed international opera professionals. French-American star Talia Stern stages the show as director of the Jette Parker Artists Programme at the UK’s world-famous, award-winning Royal Ballet & Opera theatre company. Allegra Bernacchioni, a renowned Italian opera designer who has worked in theatres across Europe and Asia, designed the set and costumes. The Opera UCT cast and chorus perform alongside the Cape Town Philharmonic Orchestra, conducted by company director Jeremy Silver and Jette Parker, conductor and pianist Peggy Wu.
Cost: R210 – R550 per person (full price) | R170 – R380 (pensioners) | R100 (students) | R150 (La Cuccina special on Sunday @ 3pm). Book now via Webtickets.
When: Thursday – Sunday, 22 – 25 October 2026 | From 7pm | 3pm (Sun matinee)
Where: Baxter Theatre Centre (Pam Golding Theatre), Main Rd, Rondebosch, Cape Town
Observatory Film Festival
Formerly known as the Obs-cene Film Festival, the Observatory Film Festival returns for its fourth year as a community-driven platform for independent and student filmmakers. The festival was created specifically to give emerging filmmakers a chance to have their work seen, addressing a gap for creators who often struggle to find an audience for finished projects.
Screenings run alongside a market of local art and craft vendors, positioning the evening as a broader community gathering rather than a straightforward cinema programme. The event is deliberately rooted in Observatory itself, framed by organisers as a celebration of the suburb’s creative and slightly irreverent character.
Beyond the films themselves, the festival is built around connecting filmmakers directly with their community and with each other, giving many participating filmmakers a first opportunity to screen their work in front of a live audience.
Cost: From R65 per person. Book now on Quicket.
When: 24 October 2026 | 6pm – 10pm
Where: Observatory Community Recreation Centre, Rawson Street, Observatory, Cape Town
Pangea
Started in 2019, Pangea has quickly become a favourite of Cape Town’s music festival scene. The event is held over four days in the Karoo, featuring wild landscapes and nonstop electronic music.
More than just an excuse to dance the weekend away, Pangea also features many workshops, yoga classes, food markets, art, and more. Featuring local and international DJs across eight floors with diverse sounds and styles, the festival takes no sponsors or product placements, focusing instead on the community and the music.
This year, the theme is “Soft Earth”, with lineups and more information coming soon.
Cost: From R2590 for the weekend. Tickets on sale on Airdosh.
When: 22 – 25 October 2026
Where: Karoo 1 Hotel Village, Touws River, De Doorns
Step It Up Dance Academy: PAGEBOUND
Step It Up Dance Academy brings its student production PAGEBOUND to the Baxter Concert Hall, following a young girl’s journey through worlds of fantasy, mystery and adventure told entirely through dance. The show combines a range of dance styles across the production, featuring the academy’s students alongside professional guest artists.
The production is structured as a storybook come to life, using shifting settings and dance styles to move the central character through different fantastical worlds before returning to an ambiguous close, leaving audiences to decide how much of the journey was real.
As a dance-only production without spoken dialogue, the show relies on choreography and staging rather than narration to carry its story, making it accessible to audiences of different ages and language backgrounds.
Cost: R190 – R320 | Booking available on Webtickets.
When: 23 to 24 October 2026 | Fri 6.30pm | Sat 11am & 4pm
Where: Concert Hall, Baxter Theatre Centre, Main Road, Rondebosch, Cape Town
Cape Town International Kite Festival
The iconic Cape Town International Kite Festival returns for its 32nd year in 2026, inviting visitors of all ages to come together and #ColourTheSky in celebration of community and mental health awareness. The event brings together thousands of kite-flyers and viewers every year, making for a vibrant and whimsical day out in the October sun.
Since launching in 1994, Cape Mental Health has hosted the city’s International Kite Festival, encouraging conversations around mental wellbeing and raising funds for essential mental health initiatives across the country.
Each year brings its own theme, ensuring no edition is exactly the same, while using each hashtag to kick-start the mental health conversation. This year is all about #ColourTheSky, a message that brings together kite-flying with the need to foster community. In the festival’s own words: “Just as every kite adds its own splash of colour to the sky, every act of compassion can bring hope, encourage connection and remind someone that they are not alone.”
As always, visitors can expect to see dynamic displays from local and international kite flyers, with huge kites taking over the spring skies over a two-day weekend. It’s an ideal day out for families, with kids enjoying the kite shows while parents join in the deeper discussion. However, the event suits visitors of all ages, with a range of interactive activities, food vendors, and kite-themed experiences on both days.
Cost: R80 per adult (day access) | R50 per child (day access) | R160 per adult (weekend pass) | R100 per child (weekend pass). Tickets available on Quicket.
When: 24 & 25 October 2026 | 10am – 6pm
Where: Youngsfield Military Base, Ottery, Cape Town
Learn more about the Kite Festival
Helderberg Open Gardens
Helderberg Hospice opens a weekend of private gardens across the Helderberg region, giving the public rare access to residential gardens not usually open to visitors. Rather than publishing addresses in advance, the hospice hands out maps only to ticket holders, protecting the privacy of participating landowners and turning the weekend into a self-guided treasure hunt.
The format suits families, groups of friends, couples or solo visitors looking to spend a weekend exploring gardens across the region at their own pace, with the specific selection of gardens changing from year to year. All profits fund hospice and palliative care services for patients and families in the Helderberg community.
Maps and full garden details are collected in person at Helderberg Hospice ahead of the weekend rather than published online.
Cost: R140 per person (weekend pass). Book now on the website.
When: 23 – 25 October 2026 | 9am – 4pm
Where: Maps issued at Helderberg Hospice, 21 Old Stellenbosch Road, Somerset West, Cape Town
Clayface
In what has been a landmark year for horror films, with overnight successes including Obsession and Backrooms, DC Studios is moving beyond the superhero genre with this year’s Clayface.
Rising Hollywood star Matt Hagen descends into a horrifying, revenge-filled monster when scientific ambition strips him of his identity and humanity.
Releasing a week before Halloween, the movie is set to be the horror watch of the spooky season. The very unsettling teaser trailer is out now on YouTube.
When: Opens in theatres on 23 October 2026
Where to watch: Likely for release at Ster-Kinekor cinemas nationwide
Terroir & Table at Cape Grace
Continuing on from the VUUR collaboration, Terroir & Table evenings begin with a welcome toast in the Bascule cellar, before moving on to four courses paired with four wines throughout. For any particular favourites, bottles are available for purchase on the night.
The Terroir & Table experience concludes on 24 October with De Grendel, the distinguished wine estate with an award-winning portfolio, hosted by cellar master Charles Hopkins, who has been with the farm since its earliest days of winemaking back in 2005.
Cost: R1200 per person. Book using Dineplan or call 021 410 7100.
When: 24 October 2026
Where: Cape Grace Hotel, W Quay Rd, Victoria & Alfred Waterfront
Dracula
After a successful run earlier in the year, Dracula is back by popular demand, showing for a final few nights exclusively on Halloween weekend.
Cape Town City Ballet presents the South African Premiere of David Nixon CBE’s Dracula, a work that has left audiences around the world breathless with its intoxicating blend of beauty, danger, and dramatic storytelling.
In this Cape Town City Ballet adaptation, the classic tale is reimagined through movement, music, and theatrical design. Set between the refined world of Victorian England and the shadowy landscapes of Transylvania, the ballet follows Jonathan Harker, a young solicitor sent abroad to assist Count Dracula with his English property acquisitions. What begins as a formal business trip quickly transforms into a nightmarish encounter with an ancient force.
As Dracula sets his sights on London, the ballet unfolds into a dramatic exploration of seduction, fear and transformation. Iconic elements such as the haunting female vampires, heightened suspense, and ever-present tension between good and evil come vividly to life on stage, as Stoker’s dark, atmospheric novel is translated into a visually striking and emotionally charged theatrical experience.
Cost: R250 – R500. Tickets available on Webtickets.
When: 28 October – 1 November 2026 | From 7.30pm | 2pm (Halloween matinee) | 12pm (final day matinee)
Where: Artscape Theatre Centre, D.F. Malan St, Foreshore, Cape Town City Centre
FAME Music Week
Music Week is a new four-day platform launched by FAME Week Africa that consolidates three music industry gatherings under a single delegate ticket. The programme runs across two Cape Town venues, the CTICC and the Protea Hotel Fire and Ice, and is designed for music professionals across all sectors: artists, managers, producers, publishers, label representatives, rights holders, educators, brands, and creators.
The week opens on 28 October with Muziki Africa, a conference dedicated to the business of African music, covering rights management, artificial intelligence, artist development, publishing, live events, monetisation, and the international growth of African sound.
From 29 to 30 October, the inaugural Pretty Loud Summit focuses on women in music, bringing together artists, songwriters, DJs, producers, managers, publishers, and executives for two days of conversation, mentorship, and industry networking.
The week concludes on 31 October with Music Exchange (MEX26), now in its 16th year and described as South Africa’s only entertainment-economy-focused industry conference. MEX26 covers innovation, sustainability, rights, entrepreneurship, and business development for music and creative economy professionals.
Cost: R150 per person. Book now on Quicket.
When: 28 – 31 October 2026 | Full programme available on the website.
Where: CTICC, Convention Square, 1 Lower Long Street, Foreshore, Cape Town
Halloween 2026
Ramfest’s Halloween edition lands in Cape Town with international Canadian rock heavyweights Silverstein, alongside South African staples including Fokofpolisiekar, Jack Parow, and Sunken State. The event builds out a full festival-style production with multiple bars, merch, and food vendors.
Other featured artists include DoomTrigger, Atlantic South, and the DJs behind Emo Night South Africa.
Fans can expect a hard-hitting lineup, professional stage design, and high-output sound for a truly immersive concert experience. Costume-friendly policies add a playful edge, while pit barriers and on‑site medics maintain safety for more energetic sections.
Cost: R350 – R450 per person. Book now on Howler.
When: 30 October 2026 | 5pm – 2am
Where: Castle of Good Hope, Castle St, Foreshore, Cape Town
Rabbit Heart: The Manor of Mischief
This Halloween, Rabbit Heart invites families to step through the gates and into a wonderfully weird world of mischief, mayhem, magic and just the right amount of spooky fun.
Across 10 interactive rooms spanning two floors, little explorers can encounter curious characters, theatrical surprises, creepy discoveries, playful challenges and plenty of things to discover on the day itself. The Manor of Mischief is designed primarily for children up to 12 years old, with an interactive experience created to encourage imagination, curiosity, play and a little bit of wonderfully spooky Halloween fun.
Every child receives a Manor Map to help them explore the house. After completing the map, they unlock a sweet treat at the end. For older, braver kids, there’s a special Teen Haunted House Experience for ages 13–18, taking place later in the day, with a darker, scarier version of the Manor.
Cost: R100 – R350 per person. Book now on Howler.
When: 31 October 2026 | Slots at 10am, 1pm & 4pm
Where: Glenhof Manor, 12 Glenhof Rd. Newlands, Cape Town
Umngqungqo Orchestral Experience
Baritone vocalist and Umhlobo Wenene FM jazz presenter Dumza Maswana brings his Umngqungqo Orchestral Experience to Artscape, following a sold-out run at Johannesburg’s Market Theatre and appearances at the National Arts Festival in Makhanda. The production combines a full orchestra, conducted by Sakhile Simani, with musical direction by Mthokozisi Mabuza, and joint arrangements by the pair.
Maswana fuses isiXhosa indigenous music with jazz and orchestral arrangement, drawing largely on his 2022 album Celebrating African Song, produced with pianist Andile Yenana and nominated for a South African Music Award. Material spans reimagined traditional melodies alongside new compositions, with Maswana occasionally playing the uhadi, a traditional Xhosa musical bow, during the performance.
Previous stagings of the show have featured a full choir alongside the orchestra, adding a large-scale choral dimension to the arrangements. The production blends storytelling with live music rather than functioning as a conventional concert set, framing each piece within a broader narrative of heritage and identity.
Cost: R250 – R400 per person. Book now on Webtickets.
When: 31 October 2026 | From 7pm
Where: Artscape Opera House, D.F. Malan Street, Foreshore, Cape Town
Cape Town Zombie Walk
South Africa’s biggest & most iconic Halloween event returns to take over the streets of Cape Town.
Each year, thousands gather for the Zombie Walk, transforming the city into a thrilling, all-ages, and pet-friendly parade of the undead. Everyone is welcome, from professional makeup artists to those coming in casual costumes, to get into character and join the horde of limping zombies for free.
The walk supports Lucky Lucy Foundation, which rescues and rehabilitates abused and neglected animals. After the walk, an 18+ afterparty lets those who want to party the night away do so in their zombie get-ups, with each ticket going to Lucky Lucy.
Attendees are encouraged to dress up as much as they want. Fake weapons are allowed (no sharp blades or firearms without an orange tip), and no alcohol may be visible. Participants must obey all directions from our marshals, medics, security, and traffic officials.
Cost: Free to join | From R100 per person (after party). RSVP via Quicket.
When: 31 October 2026 | 5pm – 6pm
Where: Starts at 109 Government Ave, Cape Town City Centre, Cape Town
Sip and Savour Festival
After devastating floods in 2026, Sip and Savour Festival is back in an all-new location. While the festival has moved to Rietvallei Wine Estate in Robertson, the programme remains the same, with each ticket including access to wine tastings at several high-profile Robertson Wine Valley wineries.
The festival offers events and activities for the whole family, with a curated selection of food stalls, live entertainment, and a dedicated Kiddies’ Zone for little ones to enjoy the Robertson winelands safely. All tickets include complimentary shuttle services in and around Robertson, with preferred shuttle slots available to be pre-booked on the Wine Valley Safari website.
Cost: R300 – R1500. Tickets available on Webtickets.
When: 31 October & 1 November 2026 | From 10am
Where: Viljoensdrift Wine Estate, R317, Robertson
HorrorFest
One of Cape Town’s most storied annual horror events returns for its 22nd edition.
This year’s festival has three major events. The premier attraction is a special 100th-anniversary celebration of Nosferatu director F.W. Murnau’s 1926 adaptation of Goethe’s FAUST. During the exclusive Halloween night screening of the landmark silent horror film, guests enjoy a live, original soundtrack performance by HorrorFest’s very own Makabra Ensemble.
The night before is the HorrorFest curtain opener, with an audience-participation screening of The Rocky Horror Picture Show, where participants are encouraged to dress up as their favourite Rocky Horror characters in honour of Tim Curry’s unfortunate passing in 2026.
The Hunchback of Notre Dame (1939) is the final event on the programme, with viewers watching a well-preserved, rare 16mm print screening for a unique cinematic experience.
Cost: R80 per person (film screenings) | R125 (live soundtrack). Book now on Quicket.
When: 28 October – 8 November 2026
Where: Labia Theatre, 68 Orange St, Gardens, Cape Town
