For long, cities grew organically, without specific design. Stellenbosch also grew organically for about 250 years. Even late in this period, individual decisions, like Jannie Marais’ donation to establish a university or Anton Rupert’s rescue of historic buildings, could significantly influence the future character of the town. Today, with larger populations and complexity, cities have to plan to ensure harmony and sustainable growth. Stellenbosch is not an exception. In land size, Stellenbosch is now more than five times bigger than it was a mere seventy years ago.