Iconic Spots Along the Cape Town Cycle Tour Route #3

Whineberg Hill is a thing of the past – although you will want most of the Blue Route freeway to recover from its brutal wake-up call.

This is the only day of the year cyclists are permitted on this ribbon of tarmac that bisects the historic Constantia Valley, famed for its vineyards and leafy suburbs. 42km riders get to do it twice, of course, with the big clover-leaf turn at the end of what is officially called the Simon van der Stel Freeway. Take your time and keep an eye out for the multiple bridges across the freeway, which will be packed with spectators, and the unicorn on your left – true story – on one of the last non-grape working farms in the valley.

On your right as you head south – again, 42-ers get a second bite at this part of the route, so on your left as you begin the long climb up towards Wynberg again – you will see vineyards aplenty, indeed Constantia remains a top-level wine producer and has been since the late 1600s. Klein Constantia is well worth a visit before or after the Cycle Tour, and its Vin de Constance is one of the world’s leading wines, the choice of the rich and royal for centuries. Even Napoleon had some shipped to his exile island of St Helena, including a glass of it on his deathbed, while Louis XVI and Marie Antoinette were no strangers to Cape wines … and it is still produced today (and delicious!).

Before you start reaching these green delights, shortly after the turnaround, you will find Pollsmoor Prison on your left – lotsa buildings and lotsa cultivated fields using the most of the fertile valley floor, many streams and rivers and a not insignificant amount of prison labour. Pollsmoor has housed many a famous name, both criminal and political, with Nelson Mandela spending some time here after his stay on Robben Island, as did Breyten Breytenbach; seven years before he ‘emigrated to Paris’.

Here’s the bet-you-didn’t-know bit for today… before the prison was built, this area boasted a motor racing track, one so good it hosted a grand prix; the 1937 Grosvenor Grand Prix welcomed the all-conquering Auto Unions (eventually Audi) of Ernst von Delius and Bernd Rosemeyer, two Maseratis two Bugattis and an Alfa Romeo in a star-studded foreign field. Von Delius and Rosemeyer prevailed, with the first local driver Duggie van der riot, finishing 7th.

Beyond Pollsmoor lies Constantiaberg, a few metres short of beating Table Mountain as Cape Town’s highest point, but boasting a collect of MTB routes that include a ride to its radio mast; the Tokai MTB network is world-class, in the middle of a bustling city.

The Blue Route climbs gently all the way from the turnaround, offering plenty of time to wave at loved-ones, who have no excuse with multiple entry points and onramps – closed to traffic for the day, but foot traffic, especially supportive foot-traffic more than welcome – before the slightly grippier ascent up the back of Wynberg, with the glorious Chart Farm on your left just before you summit, where (another day) you can pick roses and enjoy tea overlooking the magnificent Constantia Valley.