While most families are settling back into routine after the school holidays, Stellenbosch is just getting started. The Western Cape’s beloved winelands region has packed the second half of the year with an inspiring calendar of events, inviting visitors to experience the art of slow travel through food, wine, heritage, and culture.
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“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.”
Wine town takes centre stage
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From 26 July to 3 August, Wine Town Stellenbosch unfolds as a nine-day celebration across the valley. Expect specialised wine tours, vertical tastings, and winemaker-hosted lunches and dinners. Restaurants are running themed specials, while selected wine bars and eateries offer Happy Hour from 17:00 to 19:00 throughout the event.
The highlight is the Stellenbosch Wine Festival, taking place on Friday, 1, and Saturday, 2 August. With over 60 producers and nearly 200 wines to taste—including newcomers Raats Family Wines, Hidden Valley Wines, and De Meye Vineyards – it’s a showcase of the region’s depth and diversity. Food lovers are also in for a treat, thanks to a bountiful graze table of local delicacies curated by chefs Adele Grewar and Bertus Basson.
“This is our annual ‘celebration of the grape,’” says Elmarie Rabe, GM of 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.”
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Tastes, tales, and theatre
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The flavour focus continues with Taste Stellenbosch (1–30 September), a month-long celebration of the region’s culinary heritage. Participating restaurants will debut new seasonal menus and highlight local produce – a showcase for Stellenbosch’s award-winning chefs and food artisans.
In October, the Toyota Stellenbosch Woordfees (11–19 October) will light up the town with literature, theatre, visual arts, film, and music. What began as a one-night Afrikaans word-art festival in 2000 has grown into one of Africa’s largest cultural events, drawing 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.”
October rounds off with Garden Town (31 October–9 November), offering garden tours, floral installations, and a charming town hall market.
Exploring local life – and slowing down
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Beyond the headline events, visitors are encouraged to immerse themselves in the everyday magic of Stellenbosch. From Cape Dutch architecture to street food in Kayamandi, a variety of local tours offer new perspectives on life in and around the town.
Stellenbosch on Foot traces the historical heart of the region, while Kayamandi on Foot introduces travellers to local guides who share stories of resilience, culture, and home-cooked hospitality. Bites and Sites combines culinary exploration with heritage storytelling, from artisanal coffee to family recipes and biltong tastings.
For the more active, cycling tours with Bikes ‘n Wines, small-group rides with Best Day Ever, or e-bike excursions to Boschendal provide scenic immersion into wine country. Hikers can head to Jonkershoek Nature Reserve or take to the vines via Segway.
“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.”
A season to savour
Whether it’s sipping Pinotage at a fireside tasting, wandering through a garden in bloom, or discovering stories in the streets of Kayamandi, Stellenbosch’s winter and spring offerings are a call to slow down, explore deeply, and connect with the soul of the winelands.
For more on Stellenbosch’s Stay and Play offers and upcoming events, visit: https://stayandplay.visitstellenbosch.org
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