Winter in Stellenbosch is Slow, Sustainable and Full of Soul

With Stay and Play specials and a rich event calendar, Stellenbosch demands your full attention. 

STELLENBOSCH, Western Cape – Think the mid-year school holidays are over and there’s nothing left to look forward to until December? Think again. South Africa’s premier wine region is busy curating a compelling events calendar to see us through to the end of the year – and it’s an irresistible invitation to visit more, stay longer, and immerse yourself in experiences that nourish both body and soul.

“Visit Stellenbosch’s seasonal Stay and Play specials are still going strong,” says Annemie Liebenberg, CEO of Visit Stellenbosch.

“It’s the perfect excuse to experience Stellenbosch in winter, and connect more meaningfully with our place, our people, and our culture – which comes alive through wine, art, music, literature and heartfelt hospitality. It’s more than just a visit, it’s a chance to slow down and discover the stories, flavours and people that make this region so extraordinary.”

At the end of July, Wine Town Stellenbosch (26 July to 3 August) unfolds as a nine-day celebration across the region. On the to-do list are specialised wine tours, workshops, and curated vertical tastings, along with winemaker lunches and dinners, special offers at restaurants around town, and exclusive tastings available only during the event. Wine Town Stellenbosch is also the reason why Happy Hour is in full swing from 17:00 to 19:00 at selected wine bars and restaurants.

Crowning the festivities is the Stellenbosch Wine Festival, taking place on Friday, 1 August, and Saturday, 2 August. Visitors can taste some 200 wines from over 60 producers, featuring not only the region’s most renowned names but also exciting first-time participants in the event like Raats Family Wines, Hidden Valley Wines, and De Meye Vineyards. Once again, a highlight of the event is the abundant graze-table of traditional savouries and sweets by chefs Adele Grewar and Bertus Basson, continuously replenished throughout the event. With live entertainment adding to the atmosphere, the festival promises an experience as memorable as the wines themselves.

“This is our annual ‘celebration of the grape’,” explains Elmarie Rabe, GM Stellenbosch Wine Routes. “This year we’re also celebrating 100 years of Pinotage. For Pinotage lovers who want to learn more about the history of Pinotage and discover different estates, unique varietals and interesting pairings – it makes for a perfect few days away.”

Taste Stellenbosch (1 to 30 September) gives the valley’s culinary heritage a full month in the spotlight. It’s a chance for participating restaurants to unveil new menus and showcase their exceptional talent – and for visitors to experience the seasonal produce, bold flavours, and deep-rooted traditions that inspire Stellenbosch’s award-winning chefs.

Come October, Toyota Stellenbosch Woordfees (11-19 October) fills the town with the magic of storytelling, literature, theatre, art, dance and film. Now in its 25^th year, Woordfees began in 2000 at Stellenbosch University as an all-night celebration of Afrikaans word art. Over the past 25 years, it has grown into one of the largest arts festivals in Africa, attracting around 50 000 festivalgoers annually.

“This year we have a few surprises in store,” says Liebenberg. “Our beloved ‘Wynskool’ masterclasses are back with Bubby 101, Chenin Blanc 101 and Pinotage 101 sessions, plus we’re adding something really special – a ‘stapstories’ walking tour through the beautiful Banghoek Conservancy with Sophia van Taak and a Woordfees Straatsoiree that will officially launch Stellenbosch’s exciting season of Street Soirees.”

Garden Town is set to return from 31 October to 9 November 2025, with stunning displays, private garden tours and a market at the town hall.

Celebrating life in Stellenbosch

Alongside Visit Stellenbosch’s flagship events, walking tours, bike tours and dining experiences in Stellenbosch and its surrounding communities (including Kayamandi, Jamestown and the Dwarsrivier Valley), offer visitors different perspectives on local life.

Stellenbosch on Foot provides an immersive historical journey through Cape Dutch architecture and significant sites, perfect for understanding how this beautiful agricultural and academic town has evolved over the years.

For those seeking authentic cultural connection, Kayamandi on Foot’s local guides share stories of daily life, traditions, and resilience while serving home-cooked flavours with warm hospitality.

The Bites and Sites cultural tours blend storytelling with culinary exploration, celebrating the diverse heritage that shaped modern Stellenbosch through biltong tastings, artisanal coffee, family recipes, and local wine pairings.

And of course, Stellenbosch’s mild weather makes outdoor exploration irresistible. Cycling enthusiasts can glide through vineyards with Bikes ‘n Wines, join small-group rides with Best Day Ever, or e-bike from Stellenbosch to Boschendal. Prefer hiking? The stunning trails of Jonkershoek Nature Reserve await or try Segway tours through the vines.

“Our mild winter weather lends itself to outdoor adventures,” says Liebenberg. “And when it rains, it’s the perfect chance to connect with local winemakers, artists, and characters who bring our town to life.”

The Art of Slow Travel

Ultimately, winter in Stellenbosch is about family fun, unplanned moments, conversations that stretch over harvest tables, and new experiences that take you well into spring, summer and beyond.

For more information about Stellenbosch’s winter offerings and Stay and Play packages, visit https://stayandplay.visitstellenbosch.org/

For media inquiries, please contact Roland Müller at roland@bigambitions.co.za.

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