With the mid-year school holidays behind and December still a distant thought, many might assume there’s little left to look forward to. But in the heart of the Cape Winelands, Stellenbosch is proving otherwise. South Africa’s premier wine region has curated a full calendar of experiences that make the colder months not just bearable—but utterly delightful. From wine festivals to storytelling under the stars, Stellenbosch invites visitors to slow down, stay longer, and reconnect with food, culture, and community.
A Toast to Winter: Wine Town Stellenbosch
Kicking things off is Wine Town Stellenbosch (26 July – 3 August), a nine-day celebration of all things grape. Across the town and surrounding estates, wine lovers can enjoy curated tastings, winemaker dinners, workshops, and happy hour specials. The town buzzes with activity, as wine bars and restaurants offer exclusive experiences tied to the event. Crowning the week is the Stellenbosch Wine Festival (1–2 August), where over 200 wines from more than 60 producers are showcased. Among them are both iconic names and first-time participants like Hidden Valley Wines and De Meye Vineyards. Guests can graze on traditional fare from acclaimed chefs while enjoying live entertainment in an atmosphere that feels as rich as the wines being poured. This year, the festival also marks 100 years of Pinotage, with masterclasses offering a deep dive into South Africa’s homegrown varietal.
Flavours of the Valley: Taste Stellenbosch
September brings Taste Stellenbosch (1–30 September), a month-long culinary celebration that highlights the valley’s seasonal ingredients and acclaimed chefs. Restaurants across town unveil new menus inspired by bold local flavours, offering visitors a chance to explore the region’s deep-rooted culinary heritage. For food enthusiasts, it’s the perfect excuse to visit again—or stay a little longer.
Woordfees: Where Stories Come to Life
In October, the focus shifts to arts and culture with the Toyota Stellenbosch Woordfees (11–19 October). What began 25 years ago as a university celebration of Afrikaans literature has grown into one of Africa’s biggest multi-arts festivals, drawing some 50,000 visitors annually.
This year’s programme includes theatre, dance, music, film, and visual arts. Highlights include wine-focused masterclasses like Bubbly 101 and Chenin Blanc 101, a storytelling walking tour through the scenic Banghoek Conservancy, and a lively Woordfees Straatsoiree that officially kicks off the season of Stellenbosch Street Soirees.
Garden Town: A Floral Finale
From 31 October to 9 November, Garden Town brings a burst of colour and calm to Stellenbosch. Visitors can enjoy floral displays, private garden tours, and a vibrant market at the town hall. It’s a celebration of nature and design that rounds out the season with beauty and tranquillity.
Exploring Beyond the Vine
Beyond the flagship events, Stellenbosch offers immersive experiences year-round. Guided walking tours through the historic town, visits to surrounding communities like Kayamandi and Jamestown, and cultural food tours offer fresh perspectives on local life. For outdoor lovers, cycling through vineyards with Bikes ’n Wines or Best Day Ever, hiking the trails of Jonkershoek, or joining a Segway tour through the vines adds a sense of adventure to any visit. Even in the rain, Stellenbosch’s warm hospitality and creative energy shine through.
A Destination That Encourages Slow Travel
Winter in Stellenbosch is not just about what to do—it’s about how it feels. Unhurried lunches, meaningful encounters, and time spent in nature or conversation create memories that stretch well into spring and summer. For more on Stellenbosch’s seasonal events and Stay and Play specials, visit stayandplay.visitstellenbosch.org.
