A return to Kayak Chicago, the setting for Chapter 10 in my book “The Fat Paddler”

One of the greatest aspects to being a paddler is how fun it can be to explore foreign places by kayak. Visit almost any city in the world and somewhere there will be a hire place allowing you to experience the city from the water. Chicago is one of my favourite places to paddle, as the Chicago River winds through the centre of downtown (known to locals as ‘The Loop’), giving you an incredible view of immense glass towers and beautiful architecture.

Paddlers setting off at sunset for a night cruise through Chi-Town

Often city kayak centres will offer specific tours – in Chicago you can do architecture tours, crime & gangster tours (highly recommended!) and fireworks tours. The benefit of these is hearing first hand from guides about the history of the city you are visiting. Or you may just prefer the personal visual feast of a foreign city at night, with the sounds of local revelry carrying across the water as you glide by in the darkness.

Night paddling is a beautiful way to experience a city

On a recent return visit to Chicago I decided to paddle its rivers again. For me, this was a second night paddle in this city and I was just as mesmerised as I was the first time. Only this time I had five friends with me to share it with, and I almost got more pleasure watching their reaction to such a novel experience. All agreed that it was both a stunning way to see the city… as well as far more tiring than they expected – ha!

At the Chicago River downtown junction, looking east towards Lake Michigan

Chicago River downtown junction, looking south into “The Loop”

Another bonus of paddling cities is that you often get to see a little of the underbelly hidden away from the general public. Rivers running under bridges and through industrial areas often give you access to urban conditions and art that you wouldn’t ordinarily see as a tourist. Graffiti is more raw and better reflective of the darker side of the city – experiencing it will bring you far closer to your destination.

Larger than life graffiti on the concrete banks of the river. It was twice as high as I was.

After a few hours meandering through the city, there’s not much cooler than finding some local nightlife for a relaxing meal or beer afterwards. In Chicago, one of the greatest jazz and blues cities in the world, visiting one of the many jazz/blues clubs will give you a further appreciation for the real culture of the place. And let’s face it, it’s a brilliant way to end a great evening’s activities! Cheers, FP

A Chicago blues and nightlife institution – Kingston Mines (main room)

The Kingston Mines back room – harder, edgier blues rock. Yeeehaw!