Issue 25
Good morning, Winelands Insiders!
School’s back, harvest season’s here, the students have arrived, and suddenly we’re all “back at the gym” (or sprinting through Woolies to feel productive). Life’s loud.
That’s where we come in 😉
We do the digging - you get the local buzz, news and events worth knowing about.
Here’s the lineup👇
Things To Do: Events Listings
Local Business & Town News
Little Insiders
This Week’s Top Deals: Spa deal!
Weather: Mon to Wed are the best days
Mind, Health & Fitness
A Little Extra Inspo
👉 If you have any local friends who you know will love this, send them to our free signup page to join.
Let’s get to it!
Things To Do: Events Listings
Before we get stuck into the next week or so, here’s some big, not to be missed events for the calendar:
🎭 Arts & Culture Events
Andrew Young: Rockin’ All Over The World
📅 Fri. 23rd Jan. 8:15pm 📍 Drostdy Theatre, Stellenbosch
Andrew Young, a powerhouse saxophonist, with international chart-toppers & show-stopping live performances.
🎟 R275 - tickets HERE
Akkedis Se Verjaarsdagfees
📅 Sat. 24th Jan. 1-6pm 📍 Flagstone Winery
Celebrate 102 years of Akkedis with an unforgettable afternoon of live Afrikaans music, great wine & summer vibes at Flagstone Wines.
🎟 R200 pp - tickets HERE
Cohen & Diamond Journey | Mathys Roets & Johan Liebenberg
📅 Fri. 30th Jan. 8pm 📍 Simonsvlei Winery
Performed live by Mathys Roets and Johan Liebenberg, this intimate concert is a heartfelt journey through iconic songs that have shaped generations.
🎟 R200 pp - book HERE
Jo Black Live At Paul Clüver
📅 Sat. 31st Jan. 7pm 📍 Paul Clüver Forest Amphitheatre
Known for his soulful voice & heartfelt lyrics, Jo Black creates an intimate atmosphere where every song feels personal and deeply shared.
🎟 From R350 - tickets HERE
🏟 Family & Community Events
Stellenbosch Street Soiree
📅 Wed. 28th Jan. 6-8pm 📍 Drostdy Street, Stellenbosch
Wine tasting in the historic Drostdy Street - wines, food stalls & live music.
🎟 R250 pp - tickets HERE
Stellenbosch Harvest Parade 2026
📅 Sat. 31st Jan. 9-11am 📍 Stellenbosch Town Centre
This much-loved annual celebration marks the official start of the harvest season & brings together wine estate owners, winemakers, cellar teams, performers & the wider community in one joyful procession.
🎟 Free & family friendly
Vensters 2026 - Carnival Of Dreams
📅 Sat 7th Feb. 12pm-midnight 📍 Coetzenburg Rugby Fields
A joyful celebration of community, culture & youthful energy!
🎟 More info & tickets HERE
🌱 Health & Wellbeing Events
Pilates Under The Olive Trees (+ Brekkie)
📅 Sun. 18th Jan. 9am 📍 Du Vin Restaurant, Kanu Wine Farm
Start your Sunday with an outdoor Pilates session under the olive trees, followed by breakfast at Du Vin. All levels welcome. Bring your own mat.
🎟 R250 pp | [email protected]
Resolution Trail Run 2026
📅 Sun. 25th Jan. from 6:15am 📍 Dirtopia Trail Centre, Muratie Wine Estate
Kick off 2026 with one of the most loved trail runs in the Winelands.
🎟 From R75-R275 - tickets HERE
Beach Battle | Cape Town #1
📅 Sun. 25th Jan. from 7am 📍 Strand Beach
Expect tyre flips & pulls, burpees, bear crawls, farmer carries, sandbag carries, lunges, sled pulls, etc - all completed at your own pace within the race format.
🎟 R290 - R315 - tickets HERE
Sunset To Full Moon Hike
📅 Sat. 31st Jan. from 5:45pm 📍 Dirtopia Trail Centre, Muratie Wine Estate
Wander marked trails up to a scenic lookout as the sun sets over the Winelands and the moon rises, then return through illuminated forest paths under the stars.
🎟 R160 (adults) / R80 (kids) - tickets HERE
🍽 Foodie Events
JAN Franschhoek At La Motte
📅 Until 30th Apr. 📍 La Motte, Franschhoek
This exceptional, seasonal food & wine experience combines the nostalgia of a South African family table with Jan Hendrik van der Westhuizen’s Michelin-star culinary innovation.
🎟 R3400 pp - book HERE
Charles Back At The Wine Hive
📅 Wed. 21st Jan. 6pm 📍 The Wine Hive, Paarl
One of South Africa’s most influential and outspoken winemakers joins The Wine Hive for an intimate evening of storytelling, humour & exceptional wine.
🎟 R400 pp (incl wine tasting & food) - tickets HERE
Date Night At Perdeberg Winery
📅 Fri. 30th Jan.📍 Perdeberg Wines, Paarl
Enjoy a relaxed evening ft. two smash burgers, homemade tortilla chips to share, wine & a dessert for two.
🎟 R350 p couple - book HERE
Local Business & Town News
Big Brains Are Heading Our Way 🧠✨
National Top Achiever for the Class of 2025, Abigail Kok from York High School in George, is officially joining the Stellenbosch University community - and we love to see it. Abigail is currently registered for Actuarial Science, with plans to pivot into Data Science. A huge win for Stellenbosch - and an exciting journey ahead for one seriously impressive young mind.
A New Coffee Moment For Stellenbosch ☕
Babylonstoren has officially opened its first-ever Coffee Window in South Africa, and it’s right here in town. Now brewing at KwikSpar Paul Roos, this charming new spot brings Babylonstoren’s signature quality to our everyday coffee stops.
Have Your Say 📣
Kerkstraat Sundays is proposing a temporary Sunday street experiment in central Stellenbosch, exploring how Church and Andringa Streets could work with pedestrians and slower movement prioritised. Public feedback is now open and will help inform Council’s decision on a possible 11-week Sunday open-street trial. The anonymous survey takes just 3–5 minutes to complete.
Little Insiders (For The Kids)
XTERRA South Africa | Kids Race 🏃🏽♀️
📅 Sat. 28th Feb. 📍 Elgin Grabouw Sports Club
A fun, safe introduction to triathlon for kids of all fitness levels. Young athletes get to experience swimming, cycling & running in a supportive family-friendly environment. Ages 6-11.
🎟 Register HERE
💥 This Week’s Top Deals
🌿 Vergenoegd Löw Wine Estate - Renewal Spa Offer
Start the year with a moment of pure relaxation at Vergenoegd Löw’s luxury spa.
What’s included:
90-minute full-body massage (Swedish or Aromatherapy) ~ Back exfoliation with rose, lavender & geranium sugar scrub ~ Finished with a warm compress
💰 R1,070 pp | ☎️ 064 722 2728 | [email protected] (avail. until 31 Jan 2026)
🌤 Weather This Week in the Winelands
Mon to Wed are the standout days - sunny, warm & perfect for outdoor plans.
Thu 15 Jan | 24 °C / 15 °C | A breezy, brighter day |
Fri 16 Jan | 24 °C / 17 °C | ☀️ Hello sunshine! Breezy with some cloud |
Sat 17 Jan | 25 °C / 17 °C | 🌤️ Partly sunny delights |
Sun 18 Jan | 24 °C / 17 °C | 🌦️ Soft start - then easing into a calmer afternoon |
Mon 19 Jan | 27 °C / 17 °C | ☀️ Sun’s out - warm & bright |
Tue 20 Jan | 29 °C / 17 °C | 🔥 Sunshine with peak summer vibes |
Wed 21 Jan | 29 °C / 18 °C | 😎 Sunny scorcher |
Mind, Health & Fitness
Love this for the fact that you:
Don’t have to leave the house
Only 20 mins - get it done!
Only need 2 x dumbbells
You’re welcome! 👊🏼
A Little Extra Inspo
🧠 Smart Leave Planning Strategies
By optimising leave around long weekends and clustered public holidays, you can turn your 20 leave days into up to 48 days off in 2026.
Here’s your guide to maximise your leave days in 2026:
Easter Break: Take 4 leave days (7–10 Apr) → 10 consecutive days off
Freedom & Workers’ Day: Take 3 leave days (28–30 Apr) → 9 days off
Youth Day: Take 4 leave days (15 & 17–19 Jun) → 9 days off
National Women’s Day: Take 4 leave days (11–14 Aug) → 9 days off
Heritage Day: Take 3 leave days (21–23 Sep) → 6 days off
Day of Reconciliation: Take 2 leave days (17–18 Dec) → 5 days off
📌 The Big Picture
Get 45 days off with 16 days of annual leave 👇🏽
Annual Leave Hack | Discovery Bank
That’s it, you’re now up to date. No more FOMO.
Thanks for reading Issue 25 ✅
Why do we exist?
Because the Winelands has too much going on to keep missing the good stuff.
We condense it all into a no-fluff, 5-minute weekly read - events, news, weather and inspiration - delivered straight to your inbox.
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We hope it becomes your favourite Thursday read :)
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