New startup wants to take you on ‘Detour’ of Chicago

Detour-audio-walking-tour-appFrom the Saturday, Nov. 28, editions of The Daily Journal (Kankakee, Ill.) and The Times (Ottawa, Ill.) …


By Dave Wischnowsky

In the spirit of the best Thanksgiving movie ever made, there are no faster ways to cross the country than planes, no more scenic ways to see the country than trains, and no better ways to experience the country than automobiles.

But if you want to take in a city?

Well, there’s no better way to do that than by foot. And now a former Chicago tech guru is stepping up his digital game in an attempt to make urban walking tours a far richer experience for tourists than ever before.

When it comes to exploring cities on foot, my wife and I get a big kick out of it. In fact, every time we visit a new city or even return to an old familiar, we diligently conduct our research to identify its most fascinating neighborhoods, best historical haunts and most authentic establishments. Then, armed with our knowledge, we basically create our own walking tours – ones which have taken us to such fascinating locales such as a tiny bar along La Rambla in Barcelona that was Ernest Hemingway’s favorite, the cozy district of the French Quarter where New Orleans locals actually hang, and the hotel ballroom where Tony Bennett first sang “I Life My Heart in San Francisco” in San Francisco.

As cool as those experiences were, however, it’s fascinating to wonder how much fuller they could have been if that bar, district or ballroom could actually talk.

What stories would they tell?

That question is the idea behind Detour, the new brainchild from former Groupon CEO and founder Andrew Mason, which launched in San Francisco in February. Detour offers people guided audio walking tours through its app for iOS and Android that are location-aware and non-linear, with audio content changing based on the user’s path through a city.

This week, the startup announced that it will expand to Chicago, New York and L.A. in 2016. As a Northwestern alum who spent 15 years in the Windy City, Mason certainly knows Chicago, so I’m intrigued by the ways that his new company can help tourists (and locals) get to know its streets and neighborhoods more intimately than ever before.

“Detour’s walking tours are designed to take people ‘below the surface’ compared to traditional city tours or guidebook recommendations,” the tech blog Chicago Inno reported this week. “Detour says it wants to go further than simply the coolest restaurants, shops and attractions a city has to offer, but to truly understand what it’s like to live in the city you’re visiting.”

In a blog entry, the startup explained that it’s “launching cities as fully realized sets of Detours, with each walk revealing an important aspect of the city’s identity. Think of a multi-part documentary that isn’t just about a place, it’s in the place.”

Five years ago, I took an unrelated audio tour of Alcatraz that was narrated by former guards and inmates, who led me step by step through the famous prison amidst flourishes such as the noise of clattering dishes and silverware the moment you stepped inside the mess hall. It was a memorable experience, and reminds me of what Detour is now offering.

Current Detours in San Francisco cost $24.99 and are narrated by in-the-know locals such as journalists, historians, and even a local fisherman. Once the app launches locally (date TBD) Detour says, “fascinating insiders will take you into the heart of Chicago and show you what makes it tick. You’ll discover the city’s unruly gangster history, laugh with the nation’s funniest comedians and learn why baseball, architecture and notorious nightlife are all woven into the city’s identity.”

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