Good Morning, Winelands ☕️
This week leans heavily into the foodie side of life (which explains why we skipped the recipe section and went straight for interiors instead 😉). Think cosy wine dinners, long-table feasts, live music and all the comforting Winelands energy we naturally slip into this time of year.
The weather is still playing along too - dry, warm enough and perfect for morning runs, evening strolls or a relaxed 9-holes over at Paarl Golf Club before winter fully settles in.
There’s a little something for everyone here. We’ve done the snooping to find the best things happening around town, but we always love hearing about your hidden gems too. If you’ve found somewhere special worth sharing, drop us a mail at [email protected] and spread the insider love. 🫶🏼
Here’s what’s on the menu today 👇
Things To Do & Events
Community Highlights
Little Insiders
Eye Catching Deal: Something for the 1996 babies
Weather: Mellow + mostly dry
Property Of The Week
Mind, Health & Fitness: Sunday planning
A Little Extra Inspo: Interior design insta accounts
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LOCAL EVENTS
🎭 ARTS + CULTURE
MADD Thursdays at Hazendal
📅 Thu. 21 May & Thu. 28 May | 19:00 📍 Hazendal Wine Estate
Hazendal launches its new MADD Thursdays series - a curated collection of evenings celebrating music, art, drama and dance at The Marks venue. Enjoy spoken word, open mic sessions, emerging artists and expressive performances paired with excellent wine and atmosphere.
🎟 More info here
Frost & Gunn Live at Festa Restaurant
📅 Fri. 22 May | Doors 17:30 | Show 20:00 📍 Festa Restaurant, Wellington
Live music & great food - Perfect for a Friday date night or evening out with friends.
🎟 R250 pp - Book here
Biggy Live at Die Platteland
📅 Fri. 22 May | Biggy live from 20:00 📍 Die Platteland, Paarl
A high-energy Friday night with Biggy live on stage followed by DJ Pepe into the early hours. Expect big local crowd energy, music and good vibes all night long.
🎟 Free entry - Details here
🏟 FAMILY + COMMUNITY
Mud, Paw & Beers
📅 Sun. 31 May | 08:00 📍 Devonbosch
A muddy dog-friendly trail run packed with wagging tails, laughs and well-earned beers at the finish line.
🎟 Book here
🌾 HEALTH + WELLBEING
Outride Winelands Cycling Club @ Dirtopia
📅 Sat. 23 May | 08:00 📍 Dirtopia Trail Centre, Muratie Wine Estate
A relaxed social mountain bike morning with beginner to advanced routes followed by boerie rolls and drinks afterwards.
🎟 Free - RSVP here
9-Hole Sundowner at Paarl Golf Club
📅 Fri. 29 May | From 14:30 📍 Paarl Golf Club
A relaxed Friday afternoon golf competition followed by clubhouse drinks and sunset fairway views heading into the weekend.
🎟 Competition fee R40 - Details here
TEVA X TITAN Trail Run
📅 Sat. 23 May | From 06:30 📍 Cavalli Estate
A scenic Winelands trail event for runners, hikers and walkers featuring mountain views, coffee, medals and relaxed post-run vibes.
🎟 Book here
Change of Season Trail Run @ Warwick
📅 Sun. 31 May | From 08:00 📍 Warwick Wine Estate
Celebrate the change of season with flowing Winelands trails, autumn air and scenic routes rarely open to the public.
🎟 From R170 - Book here
Silent Saturday
📅 Sat. 6 June | 10:00-13:30 📍 Yogadore Somerset West
A calming half-day silent retreat inspired by the retreats of Rishikesh, India, featuring yoga nidra, walking meditation, journalling and conscious eating. A gentle reset from the rush of daily life.
🎟 R480 pp - Book here
💻 BUSINESS EVENTS
FAIL NIGHT - Real Stories. Honest Failures.
📅 Thu. 28 May | 16:30 for 17:00 📍 SU LaunchLab
FAIL NIGHT brings founders and entrepreneurs together for an honest evening of business setbacks, pivots and lessons learned behind the scenes. Expect refreshing conversations, practical insights and real stories from local business leaders and innovators.
🎟 R80 pp - Register here
UE Gala Dinner 2026
📅 Sat. 30 May | 17:30 for 18:00 📍 Erinvale Estate Hotel & Spa
An elegant evening of leadership, networking and impact hosted by Unashamedly Ethical, bringing together changemakers, business leaders and decision-makers committed to ethical leadership in South Africa.
🎟 From R1600 pp - Book here
🍽 FOODIE EVENTS
Grande Roche Winemakers Dinner x Groote Post
📅 Fri. 22 May | 18:30 📍 Grande Roche Restaurant
A refined four-course Winemakers Dinner pairing standout Groote Post wines with beautifully crafted dishes in the heart of Paarl.
🎟 R950 pp - Email to book here
Safari Couch Conversations with Chef Nic van Wyk
📅 Sat. 23 May | 16:00 📍 Safari Outdoor Stellenbosch
An interactive fire-cooking experience with Chef Nic van Wyk featuring live demonstrations, tasting bites and plenty of winter comfort-food inspiration. Ideal for foodies and braai lovers.
🎟 R250 pp - Book here
Seafood Experience with Isabella Niehaus
📅 Sat. 23 May | From 17:00📍 Festa Restaurant, Wellington
Join celebrated food personality Isabella Niehaus for a relaxed long-table seafood evening filled with incredible flavours, warm conversation and hospitality.
🎟 Details here
Cap Classique Technical Seminar 2026
📅 Tue. 26 - Wed. 27 May | From 08:00 📍 Boschendal Wine Estate
A two-day seminar hosted by the Cap Classique Producers Association featuring expert talks, tastings and industry insights into the future of sparkling wine in South Africa.
🎟 From R1000 pp - Details here
Wine Appreciation Evening at Annandale Wine Estate
📅 Thu. 28 May | 18:00-21:00 📍 Annandale Wine Estate
A cosy Vintage Shiraz & Port evening featuring curated wines paired with hearty soup, fresh bread and desserts.
🎟 R450 pp | R800 per couple - Book here
Lady May Dinner at Glenelly Estate
📅 Fri. 29 May | From 18:30 📍 Glenelly Estate, Stellenbosch
Celebrate the launch of Glenelly’s newest Lady May vintage with an elegant evening of refined dining and exceptional wine pairings at The Vine Bistro.
🎟 R1450 pp - Booking essential
Spier Winemakers’ Dinner: Master Chenin
📅 Fri. 29 May | 18:30 📍 Spier Wine Farm
Spier launches its first Winemakers Dinner of the season celebrating old vine Chenin Blanc with acclaimed cellarmaster Johan Jordaan and a beautifully paired four-course menu.
🎟 R950 pp - Book here
Sip & Savour @ The Mountains
📅 Sat. 30 - Sun. 31 May 📍 Beuld The Venue, Robertson
A cosy winter wine festival featuring tastings, winter-inspired food, live entertainment and mountain views in the Robertson Wine Valley.
🎟 From R100 - Book here
Vintages in Conversation: Cabernet Sauvignon at Simonsig
📅 Thu. 4 June | 18:00 for 18:30 📍 Simonsig Wine Estate
Explore the evolution of Cabernet Sauvignon across multiple vintages with Simonsig winemaker Nathan Valentine, paired with tasting flights and a three-course meal.
🎟 R850 pp - Book here
Pasta & Wine Making Evening
📅 Sat. 6 June 📍 Leo Sky Farm
Learn the art of handmade pasta with an authentic Italian chef while enjoying beautifully paired wines hosted by Oli’s Wine Club. Expect a relaxed evening filled with flavour, wine and Italian charm.
🎟 Book here
Top 3 foodie picks from our team…
Love Coffee Roosterkoek Days
📅 Wednesdays & Saturdays | From 10:00 📍 Love Coffee, Somerset West
Fresh roosterkoek, sliders, coffee and laid-back local vibes make this a great casual Winelands stop during the week or weekend.
🎟 From R50 - Details here
Sunday Feast at Stellenbosch Reserve
📅 Every Sunday until 26 July | 12:00 📍 Stellenbosch Reserve
A relaxed family-style Sunday lunch with roast leg of lamb and all the classic comforting sides. Perfect for slow winter afternoons in the Winelands.
🎟 R350 pp - Book here
A little bit further…
Friday Burger Night at BLOEM Restaurant
📅 Every Friday 📍 BLOEM Restaurant, Elgin
Comfort-food Fridays featuring hearty burgers & hand-cut chips - ideal for an easy dinner out or takeaway night.
🎟 Burgers from R140 - Book here
COMMUNITY HIGHLIGHTS
Slipper Day Returns on 29 May
📅 Fri. 29 May 📍 Nationwide
Reach For A Dream’s much-loved Slipper Day returns this month, encouraging South Africans to swap their shoes for slippers in support of children living with life-threatening illnesses. Funds raised help create dream experiences for children and their families across the country.
🎟 Buy a Slipper Day sticker to participate + receive a free short Wimpy coffee or hot chocolate on the day - Details here
Stellenbosch’s GoNow Scooters Still Rolling… For Now
📍 Stellenbosch
The familiar blue GoNow scooters remain part of daily life around Stellenbosch despite uncertainty around the future of the service. Loved by some and dodged on pavements by others, the scooters have undeniably changed how many students and locals move around town.
🎟 Read more here
Stellenbosch Street Store Returns This Winter
📅 Sat. 30 May 📍 Stellenbosch
The Stellenbosch Street Store returns this winter, bringing together local churches, the municipality and community organisations to create a free and dignified shopping experience for members of the homeless community. The initiative allows people to choose warm clothing in a respectful environment during the colder months.
🎟 How to get involved here
LITTLE INSIDERS (FOR THE KIDS)
Mini Ninja Opens at Winelands Square
📅 Opens Fri. 22 May 📍 Winelands Square
A brand-new indoor adventure space designed especially for little ones aged 0–7 is opening this week at Winelands Square. Created by the team behind Total Ninja, Mini Ninja offers a safe, fully supervised space packed with climbing, movement and adventure play for younger kids.
🎟 Book your visit - Details here
Fun Day at Vredenheim Dierewerf & Roofdierpark
📅 Fri. 23 - Sat. 24 May | 09:00-16:30 📍 Vredenheim Wine Estate
A family-friendly Winelands day out packed with carousel rides, inflatables, animals, slushies, pizza and outdoor fun for the kids. Don’t forget to bring bicycles for the biketrack adventure.
🎟 Details here
EYE CATCHING DEALS
Laser Hair Removal Special
📅 Valid throughout May 📍 Stellenbosch, Paarl and various other locations
The Laser Lab is offering 40% OFF laser hair removal when booking six sessions or more - ideal timing for winter treatments before summer returns.
🎟 Info here
Calling All 1996 Babies
📅 Valid until 31 July 📍 96 Winery Road
Turning 30 this year? Gather a table of four or more and enjoy 25% off your food bill as part of 96 Winery Road’s birthday celebrations.
🎟 Book here
WEATHER THIS WEEK
After a slightly cloudier Friday, the sunshine returns in full for the weekend and sticks around into Monday with highs of 22-23°C. Sat - Mon = best days.

PROPERTY OF THE WEEK
A real Stellenbosch gem just off Dorp Street - full of old-world character, polished wooden floors and the kind of charm you simply can’t recreate. With a basement wine cellar, newly converted garden flat and approved plans for additional units, this one feels like equal parts lifestyle home and smart investment opportunity.

👉🏼 Check out property here
MIND, HEALTH + FITNESS
Do this every Sunday to reset your week. Your result: more clarity + focus.
A LITTLE EXTRA INSPO
🛋 Interior Instagram Accounts Worth Following Right Now
From bold maximalism and old-world charm to sculptural modern spaces and playful colour layering, these are the interior design Instagram accounts currently feeding our renovation fantasies and saved folders.
@kellywearstler - Fearless, cinematic interiors blending Brutalist architecture, vintage pieces and rich textures with unapologetic confidence.
@donaldnxumalo - Donald Nxumalo creates chic spaces that weave bold African aesthetics, luxe textiles, and striking artwork into clean, structured, and elegant homes.
@pulpdesigns - Bold, layered interiors filled with statement ceilings, saturated colour and beautifully personal details.
@lucindachambers - A joyful rebellion against beige minimalism, packed with florals, antiques, texture and eccentric charm.
@s.t.u.d.i.o.1.9 - Pretoria-based designer Mia Widlake showcases beautiful, honest, and highly textured interiors. Her work highlights natural materials, rich neutrals, and honest, character-driven homes.
@stella_weatherall - Clever layouts, confident pattern-clashing and colourful interiors that feel both polished and deeply personal.
@geremia_design - West Coast cool meets fine-art influence with sculptural furniture, murals and beautifully unexpected combinations.
_arrcc - This design studio's feed showcases intimate, warm, and sophisticated spaces that celebrate a seamless transition between the indoors and outdoors.
@martadelarica - Warm Spanish interiors filled with vintage finds, artistic touches and elegant, lived-in sophistication.
@cabanamagazine - The ultimate maximalist moodboard overflowing with prints, colour, layered fabrics and eclectic global inspiration.
@maximilianhurd - Unapologetically maximalist interiors packed with jewel tones, vintage finds and theatrical personality.
@pieceslondon_ - A beautifully curated feed showcasing inspiring interiors, art and cultural spaces from around the world.
@barlowandbarlow - Fun, fearless interiors proving florals, scallops and playful design can still feel elevated and cool.
TOGETHER WITH
That’s it, you’re brilliantly up to date with everything happening in the Winelands (that’s worth knowing about).
Thanks for reading :)
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