Madison, WI

The Benefit of Being a Tourist in Your Own Town

Kevin Alexander
Downtown Madison Wisconsin.Photo:

For most of this past year, my family took 2–3 vacations a week. We didn’t get on an airplane (though I work for an airline), and we didn’t cross any time zones. Heck, we didn’t even get in the car.

We got on our bikes.

When planning a vacation, people look to the usual high-profile places; New York City, San Francisco, etc. Some will venture abroad, while others will hit Disney and the Florida coasts. COVID changed that calculus for most of the world.

In the middle of flyover country lies one of the most underrated cities in the country; Madison, WI. The only capital on an isthmus, it’s a small town in a small space that punches well above its weight. There is an abundance of restaurants for every taste, plenty of culture, and natural beauty at every turn (it is right between two lakes, after all). If that wasn’t enough, it’s also home to the University of Wisconsin.

It also enjoys proximity to both Milwaukee and Chicago. Being only 2 hours away by car makes it a perfect excursion during a visit to one of those towns.

All of that is true, and all of those are excellent reasons to visit. And for the most part, none of it was enough for us to stop letting day-to-day life get in the way of experiencing it.

It took a pandemic, but we finally got out and saw the city we’ve called home for 15 years. Some of the places we went, we’ve driven by 100’s of times but never really gone to. Others were old favorites made new.

When we all travel, we tend to have a lofty set of expectations. Even experienced travelers have a high bar. It’s why trips sometimes seem to fall flat. Sure, they might’ve been fun, but they aren’t always the mind-blowing experience we hope they’ll be.

In our case, we didn’t just have low expectations; we didn’t have any expectations. And really, what else were we going to do with our time? Some days we had a vague goal, like “let’s make it out to XXX,” but for most trips, the only determinant was what direction to go out of our driveway.

Something funny happens in the absence of expectations; magic and novelty.

When you aren’t hoping for much, everything is great.

Throughout dozens of rides, we found a few new restaurants, new parks, and new sights. We found spaces we never knew existed. We stopped and looked at historical markers commemorating the large and the small. We looked at community gardens. We coursed through neighborhoods that, in reality, we’re only 7–10 miles away but may as well have been on the other side of the country.

I could probably write one of those “insider’s guide to…” pieces we’ve all seen a thousand times. After all, there’s plenty here to keep one busy for days, weeks, or even years.

In fact, I did write that article for this challenge. Twice, actually. But I decided I wanted the main takeaway to be about something else, something a little different from the usual checklist of must-sees.

Wherever we went, I found myself fascinated by the idea that these entire universes were so close. All of us share the same city but live completely parallel lives simultaneously. In the end, I think that crossing those boundaries is what drives us to travel. Not just to see how the other half lives, but to experience it firsthand.

Sure, collecting passport stamps makes for good dinner party conversations, and everyone should take a road trip at least once in their lives. But when you distill it down, I think it all comes down to connection and novelty. As social creatures, we’re wired to enjoy meeting new people and experiencing new cultures.

Sometimes that happens in far-flung corners of the globe. Sometimes it occurs on an afternoon bike ride through the town you live in.

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Sharing life in Flyover Country a few hundred words at a time.

Madison, WI

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