Arts & Culture Takes Over the Winelands this October with the 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.

With hundreds of activities throughout Stellenbosch, there’s something for everyone: whether staying for a day, a weekend, or the entire festival, and whether they’re a native Afrikaans speaker or not. Here’s everything visitors need to know.

Music under the stars

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.

Jazz lovers are in for a treat with the much-loved Jazz at the Konserve series. Every evening concludes with an energetic jam session where audiences and musicians come together to celebrate the genre’s foundations of improvisation and collaboration. Guests can expect performances by The Awaken Jazz Project, the Siba Gysman Tribute Project, Heinrich Frans and the Andrew Ford Trio, and scene veterans Ramon Alexander and Buddy Wells.

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. Fans of Afrikaans rock can celebrate two decades of Glaskas, led by Deon Meiring, known for their unique blend of pop-punk, flute melodies, and sharp lyricism. Also on the programme are popular folk duo RAAF and VOLK, who are revisiting the revolutionary spirit of the Voëlvry movement through a contemporary interpretation of the iconic album Wie Is Bernoldus Niemand?

Wine, dine & unwind

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.

Elsewhere, the Hirsch Kitchen is the rendezvous for famous chefs and food personalities, including Andriette Georgiou from Mondvol, where live demonstrations, tastings, and lively conversations around local food culture take place.

Wine enthusiasts can deepen their appreciation of the Cape Winelands through Wynskool, presented in collaboration with the Stellenbosch Wine Routes team. These immersive sessions offer guests the opportunity to learn more about the region’s renowned wine heritage, discover tasting techniques, and explore the stories behind some of Stellenbosch’s most celebrated wines.

Award-winning theatre and bold storytelling

The festival’s theatre programme remains one of its strongest offerings, featuring acclaimed productions, celebrated performers, and some of South Africa’s leading directors.

Among the highlights is Grootmeise, winner of the 2026 Reinet Nagtegaal Text Prize. Written by Rachelle Greeff and directed by Lee-Ann van Rooi, the production explores an unlikely friendship between a mathematics teacher and her former student.

Audiences can also look forward to major productions including My kind druip starring Shimmy Isaacs and Joshwin Dyson, Atropa featuring an ensemble cast led by Anna-Mart van der Merwe and Antoinette Kellermann, and An Iliad, with acclaimed comedian Alan Committie bringing one of history’s greatest epics to life.

Other anticipated productions include FAUSTX, directed by internationally renowned theatre-maker Brett Bailey; Vlindervry by Wessel Pretorius; Die ander dogter starring Sandra Prinsloo; and ‘n Middel featuring Tinarie van Wyk Loots and Stian Bam.

Comedy fans can also expect plenty of laughs with stand-up performances from beloved South African names, including Committie and veteran playwright Andrew Buckland.

Classical music at its finest

Classical music remains a cornerstone of the festival, with audiences able to enjoy everything from opera and orchestral performances to intimate chamber music concerts.

Popular favourites such as Operagunstelinge III, Moederkerk-orrelweek, and Klavier-extravaganza III return alongside string ensembles, cello performances, quartets, and choirs. A particularly special occasion this year is the 90th anniversary celebration of the world-renowned Stellenbosch University Choir, one of South Africa’s most celebrated musical institutions.

Dancing with purpose

Dance takes centre stage across multiple venues as some of the country’s leading companies explore identity, culture, history, and human connection through movement.

Performances by Darkroom Contemporary, Reach for the Stars, SboNdaba Dance, Jazzart Dance Theatre, Figure of 8 Dance Theatre, the Stellenbosch Ballet Association, and Garage Dance Ensemble promise a diverse programme that is both visually striking and emotionally powerful.

Even More to Explore At Woordfees

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.