Simon’s Town Festival Returns This May with a Weekend of Adventure, Culture and Coastal Charm

This year’s edition is a more inclusive, town-wide celebration of Simon’s Town, inviting visitors and locals to explore the suburb from the mountain to the sea and everything in between. With a programme featuring everything from easygoing, intimate jazz events to fun races, the festival offers activities for people of all ages and interests.

Across the weekend, live music — curated by The Cape Town Jazz Train — brings energy to the streets and venues, with a vibrant lineup of performances setting the tone for the festival, from laid-back jazz sessions to lively gatherings.

Friday, 15 May 2026

The weekend starts with a relaxed live jazz and wine event at Bonne Esperance, a heritage home and guest house, easing guests into the festival atmosphere.

Saturday, 16 May 2026

Saturday morning is split into two events, one for those wanting a slow wander through the town before entering a lucky draw (the High Street Scavenger Hunt), and another for those wanting to race to follow clues (think Amazing Race) and try to win a cash prize (Simon’s Town Skattejag).

Visitors who want a bit more knowledge about Simon’s Town are invited to join one of two guided heritage walking tours on Saturday, one that dives into the town’s Stone Age archaeology along the coastline, and another that delves into its naval history, architecture, and social past.

Other activities include a self-paced stair-climbing Strava challenge throughout the morning and an adventure swim in Simon’s Bay.

Finally, the day concludes with the beloved Bertha’s Beersprint, a 1km race in which participants down half a pint every 200m starting from the town pier. Those with quick feet and an experienced stomach are encouraged to compete and try to take the 2026 Beer Buffalo Horns.

Sunday, 17 May 2026

The final day of the celebrations moves to the scenic Long Beach just beside the harbour. The main attraction is undoubtedly the SprintSplash, where participants move between short beach runs and ocean swims to compete for prizes. The total route comprises 1.2km (including two runs and two swims), with multiple events leading up to the ultimate 6-loop race, coming in at 7.2km.

With categories for those with varying levels of fitness and a shorter junior race for under-12s, the SprintSplash is an opportunity for newcomers and veterans to try something unique along the sunny coastline.

The weekend winds down with a relaxed Bubbles. Band. Brunch. — a laid-back brunch paired with live music curated by The Cape Town Jazz Train, bringing everyone together for an easy, festive close.

Need to know

The detailed programme, including the events and times for each day, can be found on the website. Festivalgoers are encouraged to support local businesses, from accommodation to shops, during their stay.