This May, the Western Cape invites you to experience an events calendar filled with unforgettable moments. From world-class sporting events and live performances to cultural showcases and outdoor adventures, the province offers a vibrant mix of experiences for every kind of traveler.
Whether you are chasing adrenaline, looking for entertainment, or simply wanting to explore something new, the Western Cape is ready to surprise you at every turn.
Greyton Genadendal Classics
8–10 May | Greyton
Unwind in the peaceful setting of Greyton with a weekend of beautiful music performed by members of the Cape Town Philharmonic Orchestra.
https://www.webtickets.co.za/v2/event.aspx?itemid=1587368073
Franschhoek Literary Festival
15-17May |Franschhoek
An intellectually stimulating weekend often paired with extended stays. Guests enjoy attending talks and discussions during the day, then retreating to the calm of the hotel’s gardens and lounges in the evenings.
Greyton Mountain Marathon
16 May | Greyton
Take on a scenic challenge through the majestic Riviersonderend Mountains. This trail marathon offers breathtaking views and an unforgettable outdoor experience.
https://www.entryninja.com/events/83456-greyton-mountain-marathon-2026#venue
Meiringspoort MTB & Trail Run Challenge
16 May | Oudtshoorn
Adventure meets nature in Oudtshoorn. This thrilling challenge invites both cyclists and runners to explore the dramatic Meiringspoort landscape. https://www.entryninja.com/events/83105-meiringspoort-challenge-2026
Sanlam Cape Town Marathon
23–24 May | Cape Town
Set against the iconic backdrop of Cape Town, this globally recognized marathon is a must for runners of all levels. As Africa’s first Abbott World Marathon Majors Candidate, it continues to attract athletes from around the world.
https://capetownmarathon.howler.co.za/events/sanlam-cape-town-marathon-peace-and-trail-runs-2026-6f9f/tickets
Boyz II Men Live in South Africa Tour
27 May | Cape Town
Experience the magic of live music with Boyz II Men. Known for their smooth harmonies and timeless hits, this performance promises a night filled with nostalgia and world-class entertainment.
https://www.webtickets.co.za/v2/event.aspx?itemid=1588352772
The Jive Cape Town Funny Festival
28–30 May | Cape Town
Laughter takes centre stage at the Baxter Theatre Centre as this beloved comedy festival returns. Featuring top comedians and international acts, it’s the perfect night out in the city.
https://www.webtickets.co.za/v2/event.aspx?itemid=1582738777
Winelands Autumn Expo
29–30 May | Worcester
Celebrate the flavours and culture of the Cape Winelands in Worcester. From fine wines and local cuisine to live entertainment, this event is perfect for the whole family.
https://autumnexpo.co.za/
MUT by UTMB
29–31 May | George
Set along the scenic Garden Route & Klein Karoo in George, this internationally recognized trail event forms part of the UTMB World Series. Expect world-class competition and incredible landscapes.
https://visitgeorge.co.za/event/mut-by-utmb/
From vibrant city experiences to serene countryside escapes, the Western Cape offers endless opportunities to explore, connect, and create lasting memories.
Plan your journey and discover more events in the Western Cape here:https://www.wesgro.co.za/travel/events
