Diving High From Wisconsin Skies

By Anthony Galasso

 IMAGE:  Frank Köhntopp  via  Unsplash

After watching a pair of 80-year-old women jump from an airplane, we knew there was no turning back.

It was the beginning of summer 2011. We were young, confident and a week into a month-long, booze-fueled road trip that would provide many bar stories for years to come.

Adam and I left our home base in New Jersey prepared to take on the country in my blue 2003 Ford Escape. We crawled through Pittsburgh’s bar-lined Carson Street, caught up with friends in Fort Wayne, Indiana and enjoyed a completely undeserved two-night stay at a 5-star hotel in Chicago. (Thanks for putting us up, Brittany!)

I’d say roughly 90% of the trip so far went as planned. It wasn’t until we were driving through Wisconsin that we got our first true taste of spontaneous adventure.

While driving along I-94 en route to Minneapolis for what seemed like an eternity, I spotted a small sign with a phone number on it posted onto a telephone post that read one word: SKYDIVING.

 IMAGE: Ryan McGuire via  Pixabay

IMAGE: Ryan McGuire via Pixabay

The sign couldn’t have been bigger than the 13” laptop I’m currently writing on. The fact that I saw it – or that it was even considered a useful form of advertising – was pretty amazing considering I’m almost positive we were traveling well over the speed limit.

I turned to Adam and repeated that word, “Skydiving.”

Not the type of guys to turn down a thrill, Adam and I turned the car around to retrieve the number on that tiny sign.

“Skydive Twin Cities, how can I help you?” a seemingly misplaced California surfer-turned-Wisconsin daredevil answered. For fun, let’s call him Kai – because I don’t actually remember his name.

After talking with Kai for three or four minutes, it turned out, Skydive Twin Cities was closing up for the day. But never fear…we were 100% committed to jumping out of a plane. We just needed somewhere to stay until morning.

While packing before the trip, we decided we wanted to stay at as few hotels as humanly possible, so we brought a tent with us. We figured there must be tons of campgrounds around the country that we can set up camp at for far less money than even a cheap motel. Plus, it was a hell of a lot more fun. Surely, there must have been a campground somewhere in the middle of Wisconsin that was close to Baldwin, Wisconsin where Skydive Twin Cities was located.

There wasn’t. Not that we had discovered, anyway. We had passed the nearest one nearly an hour before passing that tiny little “skydiving” sign that landed us in this situation. It didn’t make much sense to drive even further back the way we came only have to wake up even earlier to drive back this way in the morning. What were we to do?!

We slept at a truck stop in the middle of nowhere. It was called “Super Truck Stop” and it wasn’t all that super.

By that, I mean we slept in my Escape in the middle of a field filled with tons of tractor-trailers. It was actually kind of humorous to see my tiny SUV nestled in alongside all of these massive trucks. We grabbed a cheap dinner at the truck stop restaurant where people either gave us funny looks or didn’t notice us at all. I had two eggs over easy doused in hot sauce.

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That night might have been one of the coldest, most uncomfortable nights I’ve ever spent sleeping in my car. It’s the end of May, mind you, and we’re in Wisconsin. Even though it’s summer, the temperature still dropped to the upper 30’s that night and all I had was a thin blanket. Not to mention, it was pretty evident that a few of the truckers at Super Truck Stop were having some kind of party. It didn’t exactly sound like a fun party though. In fact, it probably wasn’t a party at all. I’ll never know what was happening – and I don’t think I want to.

The Day of the Dive

Morning came. We headed for the Super Truck Stop restaurant for a quick bite to eat. Again, I had two eggs over easy doused in hot sauce, an inexpensive staple of mine, and chugged a mug or two of coffee, which would later prove to be a bad idea.

Adam and I met Kai at Skydive Twin Cities and signed all the paperwork. We were then ushered into a room with roughly seven or eight other eager skydivers – two of which could have passed for my grandmother. We sat through the necessary training videos, which clearly haven’t been reshot since ‘92. We were tandem jumping with professionals, mind you, so these training videos were useful…but I couldn’t help but wonder whether or not the pro-skydiver I was going to be strapped to had seen something more recent.

I called my aunt to let her know that I’d be jumping out of a plane in a couple hours – just because she gets a kick out of that stuff – and hit the vending machines. That’s when that morning’s coffee hit me.

I ran for the musty, old bathroom at top speed not realizing that my nerves had been tightening up. I was about to jump out of an airplane. What on earth was I doing? This was something I’ve always wanted to do, but why? And why now? I was embarking on what was, at the time, the most amazing trip of my life and I was already risking my life less than a week into it.

After finishing up in the bathroom, I went to find Adam who happened to be chatting it up with the two elderly women from our training session.

“It’s my birthday,” one of the women said. “I’m 80 years old and I’m not getting any younger. When you get to my age, there are certain things that don’t scare you anymore. Jumping out of this airplane should be a piece of cake.“

I was amazed! Here I am getting nervous to the point of nearly shitting my pants when I should really be approaching this amazing part of our adventure with the same spunk as the birthday gal. Her bravery challenged me.

“I’m Lilly, by the way. And this is my friend, Janet. She’s been my best friend since we were kids. We do everything together,” she said.

With a big smile, Janet greeted us and we all continued to all chat about where we were from, the trip we were on and Super Truck Stop. You know, typical small talk until they were called to take off.

Thirty minutes later, I was strapped into my harnesses alongside Adam as we watched Lilly and Janet – the two daredevil best friends – fall ever-so-gracefully from the sky. With their respective professionals strapped to their backs, they each met the Earth a little harder than we all thought they might. Still, they popped up, high from the sheer adrenaline coursing through their veins, with big smiles and unbridled laughter.

Our group was next.

We awkwardly boarded the plane two-by-two. We were strapped to our skydiving professional, which made walking a bit tough. After we sat down, the pilot gave us a pep talk and we took off. To this day, I still say the ascent was the scariest part of the jump. You don’t actually realize how high you’re jumping from until you’re way above the clouds and the airplane hangar itself starts to look like a speck of sand in the distance.

We were given some last-minute reminders before the little red light turned on and they opened the door.

Again, two-by-two, we approached the door. When it was my turn, we sat on the edge of the plane with our feet dangling out. It was amazing. In that moment, I felt a high wash over me, simulating every emotion I’ve ever felt in my entire life.

It was probably the adrenaline.

That’s when the pro I was attached to said, “Alright! We’re gonna jump on three! Are ya ready?!”

Barely able to speak but ready to press on, I gave him the thumbs up.

“Alright! One…!"

The wind was blowing so hard, he was practically screaming at me. Still, I was so high on life, I could barely make out what he was saying.”


And that’s when it happened. This asshole pushed me out of the plane without saying “three!”

Before I knew it, I was falling closer and closer to the earth. The guy I was attached to flipped me upside down for a split second so I could watch the airplane as it quickly resembled that of a toy model. After he flipped me back, I realized we had a long way to go until we would become one with the earth again.

There were roughly sixty seconds of free-fall, which is a hell of a long time when gravity is piledriving you into the earth. Throughout that time, I don’t think I’ve ever felt more at peace. The wind is tearing through your hair. Your body is kicking into overdrive, simply trying to make sure your organs don’t fail from shock. And in those sixty seconds, I was the most badass person not on this planet.

Once Adam and I landed, that high lingered throughout the rest of our month-long road trip – taking us all the way out to Seattle, down the Pacific Coast Highway, through the American Southwest to New Orleans and back up to Jersey.

We left each stop along that trip with a new story to tell. Oddly enough, a tiny, barely legible sign along a highway in Wisconsin led to the greatest high of my life.

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