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Masked Masterpieces

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Welcome to Stellenbosch – South Africa’s second oldest town and most inspiring wine, food, art and cultural destination.
Stellenbosch art

Masked Masterpieces – Inspiration for a caring community

‘All art should inspire and evoke emotion. Art should be something you can actually feel.’

Stellenbosch is indeed an inspirational town. A leisurely walk through its streets or simple journey down the R44 will immerse one in a world of incredible art, showcasing a powerful message.

With the introduction of Masked Masterpieces, a compelling outdoors arts initiative sponsored by private individuals and companies, this has taken the shape of a supersized and striking visual reflection on the challenges of our time.

Dotted across numerous galleries and museums throughout Stellenbosch, the Masked Masterpieces are driven by Stellenbosch University bursary students in the ‘missing middle’ category, studying at the Faculty of Arts and Social Sciences.

To support these students, who have been affected financially by COVID-19, we encourage residents and visitors to contribute to the bursary fund. This is done by snapping the SnapScan QR code available at each of the outdoor art pieces.

Stellenbosch art

With sunny days ahead, now is the perfect opportunity to embark on an arts encounter and explore all the wonderful open-air exhibits and the beauty of Stellenbosch along the way.

What better way to capture all five masterpieces than on foot or by bike? Pair an inspiring day of artistry with a delicious meal at one of Stellenbosch’s cosy restaurants or browse the boutiques that line the oak-lined avenues.

But first, start your day off with a good cuppa joe. De Warenmarkt is renowned for its brews, friendly baristas and fresh pastries. It’s the perfect place to kickstart your art adventure with Adventure Shop.

Your first masterpiece of the day is none other than Vladimir Tretchikoff’s ‘Chinese Girl’, located on the corner of Plein and Drostdy streets. Just a short hop away is the Local Works / Local Spens, an ideal quick stop for souvenir shopping or perhaps stock up on biscuits, nuts and dried fruit for padkos along the way.

Pick up your bike and helmet. It’s time to put pedal to the metal as your second Masked Masterpiece awaits. Irma Stern’s ‘The Initiate’ is displayed on the wall next to the GUS gallery in Dorp Street, ready to be admired.

Stellenbosch art

Continue down Dorp Street and visit Oom Samie se Winkel. Take a trip back in time when you enter its early 20th century walls.  Browse sweet treats, bites, bits and bobs from yesteryear. You won’t want to leave empty handed. After some retail therapy, it’s on to your next art piece, Gerard Sekoto’s ‘Senegal Woman’, displayed on the gabled wall of the Distell building on Stellenbosch’s R44.


Next on your art journey is Zanele Muholi’s ‘Aphelile IV Durban’, located at the Stellenbosch Taxi Rank in Bird Street. By this time the clock has surely struck 12pm, making for the perfect stop at the Bartinney Wine Bar. After a glass, or 2, make your way to your final masterpiece; Maggie Laubser’s ‘Portrait of a coloured girl’, which can be found on a nearby wall in Bird Street’s Dorp Alley. Of course, by now, your legs are tired and your stomach rumbling, so why not grab a few plates of Genki sushi, or if you are in the mood for more of a wine bar vibe, Brampton is for you. They have the most scrumptious wine bar snack plates and flatbreads.

Stellenbosch artwork

Five fantastic works of art under your belt, and a few miles on your bike, the swansong on this adventure is a cycle up Church Street, renowned for its quaint stores and coffee shops. Revel in the town’s historic center as you return to Adventure Shop and stretch your legs after an exhilarating cycle.

If you are looking for more ideas and itinerary inspiration, contact the Visit Stellenbosch Visitor Centre at 47 Church Street, Stellenbosch or call 021 886 4310 / email