Fabric of America: Tremonte's Barber Shop in Wauconda, Illinois

My parents are retired and/or semi-retired, but they seem like they’re almost as busy as when they both had full-time jobs. Living in an “active adult” community is hard work! It reminds me of the chaos and excitement of going away to college, but forty years later.

When we visited them, it was like they were never around, and we were the ones with all the free time! Ha.

I know they love their lives, and it is what it is. That doesn’t mean it’s not the topic of jokes around our family, though. These are my folks.

What I’m trying to lead into is how we met Will Tremont. This is Will.

Will is a barber, and this is his shop.

No, I have no idea why his name is Tremont and his shop is Tremonte’s, but I’d gather that it has to do with the evolution of family names. My family name itself was spelled a dozen different ways in multiple alphabets over the centuries – with accents thrown in and tossed out for good measure – so I have no grounds for complaint.

Also, this is one of his dogs, Cash. Cash is in charge of marketing.

Anyway, my mom is into poetry, storytelling, theater, and basically public expression of any kind. She takes part in storytelling groups, goes to see storytellers, and all those kinds of things. And that’s how she met Will.

Will is a storyteller. He’s a natural-born storyteller. Within five minutes of meeting the guy, you can tell that storytelling is in his blood.

But storytelling is not why we wanted to meet Will. Will is actually a barber. And he has a traditional barber shop in the small town of Wauconda, Illinois, which is about 45 miles northwest of Chicago.

Being that Will is a barber, I guess we can complete the circle by saying, Of course Will is a storyteller. He’s a barber. Think about it.

So we went to meet Will. I needed a haircut and a shave, so we played phone tag for a few days and eventually locked down some time to invade his life and have him take a Number 1 blade to my face, head, and neck.

First though, we had to eat. Because eating rocks.

After a nice lunch with my folks in at Docks Bar & Grill on Bangs Lake in Wauconda, we headed over to Will’s shop.

Parking on the revitalized Main Street in town, we were immediately greeted by these scissors in the pavement outside Will’s front door.

Entering the shop, banter was in full force as Will shot the business with a customer. The four of us sat down, gazing at his insanely large collection of shaving mugs.

And razors.

And other memorabilia that would have any barber – or any fan of vintage Americana – go completely green with envy.

While we were waiting to pepper Will with questions, we noticed a stack of newspapers from Iowa, sitting on a chair. And they all had Will’s name on them. Because of course they did.

Will writes for a paper in his mother’s hometown, simply because it gives him the freedom to tell stories. And many of those stories come from his dad, an Italian-American kid who grew up in Chicago.

One of these cross-woven stories we heard from Will was about his dad cutting people’s hair, back in the day, in Chicago. When his dad was something like 12 years old, he would go around to all the people downtown, earning money by giving haircuts to grown folks.

The barbers were all unionized at this time – I’m not sure how formal that was, since everything from the most legit to the most criminal in Chicago is unionized in one way or another – and one of the barber reps caught up with Will’s dad on Canal Street.

His dad was picked up and told not to be encroaching on other barbers’ territory, or else. So what was the lesson he learned? Don’t get caught.

I think that somehow stuck with Will. When Will finished college in the 70s and was working for a bank, he decided one day that he didn’t want to have a day job anymore. A day job at a bank didn’t exactly fit the bill for Will. Will wanted more. Will wanted freedom.

He sat with his girlfriend, thinking about who has freedom. Who makes their own hours, comes and goes as they please, and owns their own business? Barbers.

And so it would be. Will would be a barber. He’d quit his day job, go to barber school for nearly two years, and one day have his own shop.

After taking classes, passing tests – apparently they had fairly detailed anatomical and health-related written tests back then – and doing an apprenticeship, Will would be an honest to goodness barber.

He’d eventually become a “stylist” in Wauconda. That was really a way to get a barber job at a shop, as fashionable gents around this time decided they wanted more from their barbers. And for their luscious locks. The longtime shop owner in town wanted to add that to his repertoire, so he wanted a stylist. And Will said, You know what, I can be a stylist if that’s what he wants to call me.

And so it was.

After several years of working for that guy, Will opened his own shop on Main Street in Wauconda. It did move once, but has been at this spot for nearly 30 years.

Will told us all sorts of amazing anecdotes during our time spent with him – the most glorious probably being the one about the Albanian barber he hired – but those are stories best left told by the man himself. (Download the full conversation in mp3 audio format at the end of this post.)

Throughout all these years, Will has watched the Main Street area of Wauconda thrive, fall into vacancy and disrepair, and then experience a revitalization in recent years. He’s been here all along, and is happy to see independent businesses bring central Wauconda back to life.

This includes Honey Hill Coffee Company, just a couple doors down from his shop. It was one of the first to come back to the Main Street area, and is thriving after almost a decade in its downtown location.

After hearing all of these stories about his own path and the recent breath of life that has been injected into Main Street, we asked Will if he thinks he lives the American Dream. Being that his profession is an quintessential part of the Fabric of America, history itself qualifies him as someone who can best answer this question.

When pressed, he told us a story about golf and golfers and the people who work on golf courses. He talked about the highfalutin businessman types who frequent the course with him, and how they were all jealous of one of the landscapers.

He would spend his summers in the States, making money and hanging out with his U.S. mistress. During the winter, he’d go down to Mexico and spend time with his family.

These fancy-pants, suburban corporate gents were all jealous of this guy. Of the freedom he has and the things that he gets to do. Suits, green with envy over a Mexican landscaper. Go figure.

But, as noted earlier in this post, Will loves that he gets to set his own hours. Not only that, but he can go home whenever he wants, close shop whenever he wants, go golfing whenever he wants, or go in the woods with his dogs and photograph nature when he wants. He can tell stories on stage for fun, or do magic for fun, or support a non-profit for fun. That sounds like the American Dream to us, no?

It might not be your dream, but it seems to us that Will lives his idea of what the American Dream is and can be. And we certainly agree.

If you want to hear our entire conversation, complete with anecdotes of Albanian barbers, antique shaving mug fetishes, how Will ended up as a magician on TV, or a zillion other interesting tales of a man about life, click here to download the mp3 of our conversation.

Thanks very much to Will for giving us so much of his time. Thanks for the haircut and shave, and thanks for being willing to share so much during our time there.

Download the full interview right here, or stream it below.

Tremonte’s Barber Shop is located here:

113 S. Main St.
Wauconda, IL 60084
Tel: +1 (847) 526-8909

You can also visit Tremonte’s Barber Shop on Facebook and Yelp.

Note: Thanks to our friend Pedi aka Jesus Face for editing some of the audio and making it sound reasonably decent so we could post the whole story in audio format.

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Any thoughts about Will or our conversation about the Fabric of America? Ever been by his shop, or visited Wauconda? Any other thoughts? We’d love to hear from you in the comments!