Hey there, Stellenbosch!
Welcome back to The Winelands Insider - your weekly guide to what’s happening, so you never miss out 👀
The heart of Stellenbosch is alive with rhythm, art, and local flavour this week! From the Toyota Stellenbosch Woordfees and its star-studded Music Festival send off to creative showcases like KAMERS/Makers in Franschhoek, there’s no shortage of inspiration (and great wine) to go around.
If you’re more about sunshine and sneakers, this weekend’s trail runs and Pinktober fitness events bring all the good vibes outdoors - while Oktoberfest celebrations and family festivals add a splash of fun to the mix.
And don’t miss the latest local wins - with Babylonstoren and Stellenbosch winemakers flying the flag high on the global stage.
Here’s what we have for you this week 👀
Things To Do: Events Listings
Little Insiders (for the kids)
Local Business & Town News: Babylonstoren wins gold!
This Week’s Top Deal: Rozendal Farm
Weather: Best days = Fri, Sun & Mon
Mind, Health & Fitness: Breast Cancer Awareness Month
A Little Extra Inspo
❤️ P.S. If you have any local friends who will be interested in staying up to date with what’s happening in the Winelands, send them to our free signup page 😊
Things To Do: Events Listings
🎭 Arts & Culture Events
Toyota Stellenbosch Woordfees: Music Festival Magic
📅 14-19th Oct 📍 Stellenbosch
The 2025 Toyota Stellenbosch Woordfees is in full swing & this week’s Toyota Music Festival promises to be a standout celebration of rhythm and artistry. Expect a transformative blend of genres - from soulful jazz to modern alt-pop - all reflecting South Africa’s creative pulse.
ℹ️ Here’s the full Woordfees Music line-up
🙌🏼 Woordfees Music standouts you do not want to miss:
Drie Van Die Bestes
📅 Sat, 18th Oct, 4pm 📍 HMS Bloemhof Sentrum
With Roets, Niehaus & Geldenhuys blending timeless favourites & fresh a cappella sounds, this dynamic trio promises an unforgettable musical experience.
🎟 From R200 p.p. - tickets HERE
Roan Ash & Brandon Miles
📅 Fri, 17th Oct, 7pm 📍 Jan Marais Nature Reserve
South African-born, Nashville-based Roan Ash brings his soulful country-rock sound & lyrical honesty to the Woordfees stage, joined by rising star Brandon Miles.
🎟 From R200 p.p - tickets HERE
Zoid Psalms
📅 18 & 19th Oct, 7pm/8pm 📍 Kruiskerk
Experience Zoid Psalms - a groundbreaking fusion of sacred organ music and Karen Zoid’s rock energy, creating a powerful and one-of-a-kind spiritual sound journey.
🎟 From R150 p.p - tickets HERE
KAMERS/Makers
📅 28 Oct-2 Nov, 9-5pm 📍 Allée Bleue Wine Estate, Franschhoek
Discover South Africa’s finest local designers, artisans, and fashion talent in a vibrant marketplace set among the beautiful vineyards of Allée Bleue Wine Estate. It’s the perfect place to find unique, locally made treasures while sipping on fine wine and soaking up the creative energy of the season.
🍷 A must-do event for lovers of style, creativity, and local flair!
🎟 R110 - more info & tickets HERE
Visual Arts Opening | Woordfees 2025
📅 Exhibition open daily | Online Art Auction closes 21 Oct at 2pm📍Stellenbosch Town Hall
Visit the Town Hall to experience Part 2 of the Toyota Stellenbosch Woordfees Visual Arts Exhibition - a free showcase of works by established & emerging artists. Curated by award-winning duo Heinrich Groenewald and Shona van der Merwe (RESERVOIR), in collaboration with Strauss & Co.
🎟 More info HERE
Wilderer Oktoberfest at La Grapperia
📅 Fri, 18th & 25th Oct, 10-6pm 📍 La Grapperia Pizza & Bistro, Spice Route, Paarl
Grab your lederhosen & join the fun! Celebrate Oktoberfest with a traditional Bavarian menu, beer on tap from @capebrewingco, Wilderer schnapps, live music by The Wurstzipfel (12:30–3:30) & festive games - including a best-dressed competition.
🎟 More info HERE

Wilderer Oktoberfest @ La Grapperia
🏟 Family & Community Events
Come Alive Silent Disco
📅 Sat, 18th Oct, 7am 📍 Strand Beach
Start your weekend with music, movement, and sunrise energy on the beach. The Come Alive Silent Disco isn’t your usual dance event - it’s a facilitated sunrise experience where play meets purpose. Slip on your headphones, feel the rhythm, and move as one with the ocean breeze. Perfect for families, friends, and anyone looking to start the day inspired. After the boogie, we’ll give back with a beach cleanup 🌍 - pls bring a bag.
🎟 R170 - more info & tickets HERE (book by 16 Oct)
Perdeberg Family Festival
📅 Sat, 25th Oct, from 10am 📍 Perdeberg Cellar, Paarl
One of Paarl’s most anticipated family days returns! Enjoy a full day of wine tasting, sabrage, live music, lawn games, kids’ rides, and delicious food. Bring along a picnic blanket and soak up the festive atmosphere with family and friends.
🧺 Pre-order a picnic box (R350) and enjoy it under the trees with a glass of Perdeberg wine in hand.
🎟 Book tickets HERE
Afrikaans 100 Feesmark - Kom Matiekie Saam!
📅 Sat, 25th Oct, 11-7pm 📍 Afrikaanse Taalmonument, Paarl
Celebrate Afrikaans with a family-friendly cultural fiesta as Afrikaans Amptelik 100 culminates in a grand gathering at the Taalmonument. This is an event for all ages.
🎶 Performances by riel dancers, folk dance groups & headline artists: Nadia Louw, David Fourie, Nadine & Jak de Priester, and the Kaapse Lawaaimakers
🎟 Tickets HERE
🌱 Health & Wellbeing Events
Spring Trail Run | Dirtopia
📅 Sun, 26th Oct, 8-10am 📍 Warwick Wine Estate, Stellenbosch
Lace up & hit the trails for the Spring Trail Run at Warwick Wine Estate, hosted by Dirtopia - a local favourite for trail lovers. Enjoy a scenic route through vineyards & mountain views, followed by great post-run vibes at the estate.
🎟 Enter & get tickets HERE
Pinktober at Maties Gymnasium 🎀
📅 17 & 24th Oct 📍 Maties Gymnasium, Stellenbosch University
In honour of Breast Cancer Awareness Month, Maties Gym is hosting a series of open fitness events: from high-energy circuits to themed spin sessions - raising awareness & celebrating strength in pink. Don’t miss these special editions:
• EnduroFit: Pink Edition - 17 Oct | 17:30 - 18:15
• Sunset Spin: Pink Rush Edition - 24 Oct | 17:15 - 18:00
Arrive strong, arrive pink & join the movement for a cause!
🎟 Book HERE
Blouklip Trail Run
📅 Saturday, 25th Oct, 7am 📍 Waterford Estate
Get ready for one of the most breathtaking & exclusive trail runs in the Winelands. The Blouklip Trail Run takes you across trails cut open only once a year, winding through pristine farmlands & rugged mountain terrain - a true bucket-list experience for trail enthusiasts.
🎟 Enter & get tickets HERE
Run & Ride for Renosterveld
📅 Sun, 26th Oct, 7:30am 📍 Jordan Wine Estate
Join Jordan Wine Estate for a day of exhilarating trail running & cycling through the breathtaking beauty of Stellenbosch - all in support of Renosterveld conservation, one of South Africa’s most endangered ecosystems. Whether you’re on two feet or two wheels, every stride & pedal helps protect local biodiversity. After crossing the finish line, gather with family & friends on the Protea Lawn to celebrate with good wine, music, and nature.
🎟 Book tickets HERE

Renosterveld Run | Ride
🍽 Foodie Events
Vintage White: A Celebration of White Wine Elegance
📅 Sat, 18th Oct, 10am-6pm 📍 Quoin Rock Wine Estate
This is more than a tasting - it’s an exclusive exploration of white wine excellence. Sip your way through Cap Classique, Rosé, and White wines guided by the winemakers themselves, in a day that celebrates the art and science behind every glass. An immersive experience for true wine lovers (Limited to only 25 guests).
🎟 More info & tickets HERE
Spek & Bone x Ex Animo Wine Co - Wine Fest 2025
📅 Sat, 25th Oct, 12-3pm 📍 Spek & Bone, 84 Dorp Street
It’s time to sip, swirl, and savour your way through a day of great wine & delicious food right in the heart of Stellenbosch.
🎟️ R495 p.p. (includes all wine and food tastings) more info & tickets HERE
One Night Only: Food, Wine & Wild Stories at 96 Winery Road
📅 Sat, 25th Oct, 6pm 📍 96 Winery Road, Stellenbosch
Gather around the fire for a night of good food, fine wine, and shared stories under the Winelands sky. ✨ Together with Arendsig Winery, Wild Kalahari, and Cape Wagyu, the 96 Winery Road team has crafted a feast worth lingering over:
🎟 R750 p.p. (includes wine) | Book via: wineryrd(at)mweb.co.za
Little Insiders (For The Kids)
Liewe Heksie En Die Wals
📅 18 & 19th Oct, 9am 📍 Drostdy Theatre, Stellenbosch
What happens when Liewe Heksie joins Blommeland’s own Strictly Come Dancing? 🌸 Can she even waltz? From the award-winning team behind multiple KKNK Kanna wins and Best Children’s Theatre nominations.
🎟 More info & tickets HERE
Local Business & Town News
👏🏼 Stellenbosch winemakers dominate prestigious Diners Club awards shortlist
Stellenbosch winemakers dominate prestigious Diners Club awards shortlist. Six winemakers have been shortlisted to compete for the prestigious Winemaker of the Year award, while five will vie for the Young Winemaker of the Year title. Read more here.
🏆 Babylonstoren Wins Big in Global Travel Awards
We’re celebrating some homegrown pride in the Winelands this week! Babylonstoren Farm Hotel has just been named Best Hotel in Eastern & Southern Africa in the Condé Nast Traveller UK Readers’ Choice Awards 2025 & that’s not all. Condé Nast Traveler US readers also voted it the Second Best Hotel in South Africa.
These international honours, chosen by travellers from around the world, recognise Babylonstoren’s signature blend of authentic farm living, slow luxury and heartfelt hospitality. A huge congratulations to the team & to every guest whose votes helped make this local gem shine on the global stage. ✨
This Week’s Top Deal
💥 30% OFF at Rozendal Farm, Stellenbosch
15 October - 18 December 2025
Escape to the winelands before the festive rush & enjoy 30% off selected apartments. Nestled just 10 minutes from town, Rozendal offers peaceful farm-style living with breathtaking views of the Jonkershoek mountains. Surrounded by top restaurants & wine farms, it’s the perfect spot to unwind, reconnect, and savour the slow life.
🎟 Book directly via Rozendal Farm
🌤 Weather This Week
Spring is in full swing & Stellenbosch is serving up a bit of everything this week - sunshine, a few breezy spells, and the kind of warmth that makes a wine farm lunch sound like the only sensible plan.
Best days = Fri, Sun & marvellous Monday.
Date | High / Low | Description |
|---|---|---|
Thurs 16 | 20° / 9° | ⛅ Sun & clouds, breezy in afternoon |
Fri 17 | 26° / 14° | 🌤️ Warmer with partial sunshine |
Sat 18 | 21° / 14° | 🌤️ Mix of sun & cloudy day |
Sun 19 | 24° / 12° | 🌤️ Pleasant, lots of sun, breezy pm |
Mon 20 | 28° / 15° | 😎 Glorious day, warm & sunny |
Tue 21 | 24° / 14° | 🌤️ Sun & clouds throughout the day |
Wed 22 | 23° / 13° | 🌤️ Sunny with some clouds |
Mind, Health & Fitness
October is Breast Cancer Awareness Month - a time to honour survivors, remember those we’ve lost, and encourage every woman to prioritise her health.
Early detection saves lives. Regular self-examinations, annual check-ups, and mammograms remain the most powerful tools for early diagnosis and effective treatment.
💡 Know the signs:
A new lump or thickening in the breast or underarm
Changes in size, shape, or texture
Nipple discharge or inversion
Redness, swelling, or dimpling of the skin
This month, take a moment to check in with yourself & remind the women in your life to do the same. Together, we raise awareness, support one another, and spread hope. 🌸
👉 Find local awareness events & fitness fundraisers throughout the Winelands, including Maties Gymnasium’s Pinktober Series and more.
A Little Extra Inspo
We leave you with a little dinner inspiration - fresh, healthy & wholesome. 🌱
Asparagus Risotto 💚
That’s it! You’re Now Up To Date ✅
Thanks for reading Issue 13 - we hope this becomes your favourite Thursday read!
👉🏼 Got an event, story or feedback to share? E-mail: hello(at)winelandsinsider.co.za
📲 Don’t forget to follow us on instagram: @winelandsinsider

