Working Class Man Visits Wealthy America, Results Will Shock You

I’m happy to say I visited high society and parties among the elites and made it out alive.

I’m officially back from Maine after a trip that nearly turned into an absolute disaster. For those of you who didn’t read my part one breakdown, I was in Maine for a wedding for two close friends - including a member of a legendary and now-defunct social group from a simpler time in life - and to say the wedding was legendary would be an understatement.

It was without question one of the most impressive weddings that I’ve ever been to. The gorgeous scenery of Maine was breathtaking, the alcohol situation was unbeatable and it was very neat for a blue-collar guy like myself who came from rural Wisconsin to be surrounded by some of the most elite people in America. One might say I had to pinch myself in order to believe it was all real. I’d tell you who was there, but I think guys in black helicopters and SUVs would show up for a conversation that would be less than friendly.

How did I rebound from disaster in Maine?

Early Sunday morning, my fiancée alerted me to some terrible news:

Our flight back to Washington, D.C. had been canceled and the quickest we could return to the Hookstead Compound (location classified) was Tuesday night.

I was left with the following three choices:

• Roadtrip to Boston and try to catch a flight Monday.
• Stay in Maine, move to a secondary location and ride out the situation until Tuesday night.
• Request immediate emergency authorization for a private jet to get us out.

The conversation with my fiancée didn’t last long. The private jet was a no-go, a roadtrip wasn’t realistic and left us with only one option. We packed our working class Mercedes and headed to Bar Harbor, Maine.

At this point, I’ve just accepted that we’re in a less than ideal situation. I can either get upset about it or I can embrace it. There aren’t any other options on the table.

I decide to roll with it and within a few hours, we’re in Bar Harbor. Ironically, I had to swing by the *MASSIVE* estate the groom was staying at (the most beautiful views I’ve ever seen) to drop off a gift we had forgotten the night before, and I explained to him the situation we were in.

Without hesitation, he told me to start driving to Bar Harbor. Little does he know the decision has already been made.

David Hookstead. (Credit: David Hookstead)

Fortunately, we were able to book a hotel downtown near the water on incredibly short notice. I don’t know anything about Maine other than my 2017 visit to a rural part of the state. I’m told over the course of the next few days that I’m very lucky to have been able to find a vacancy. Trust me when I say that my wallet doesn’t feel lucky, but again, I’m rolling with it.

I’m not going to lie to you. I felt a bit like a fish out of water at first in Bar Harbor. I come from the small town of Randolph, WI. It’s full of working-class people with big hearts and unbeatable work ethics, but there are not many well-off people.

Bar Harbor is the kind of coastal island most people back home couldn’t dream of stepping foot on, and yet, here I am. Little old David Hookstead strolling around gorgeous scenery and mega-mansions.

One of the first things I see upon arriving at the island is the massive yacht of a former NFL owner. This thing was an absolute beast of a vessel. Right next to it? One of the largest sailboats I’ve ever seen. I’m not in Wisconsin anymore. That’s painfully obvious at this point.

A massive yacht in Bar Harbor. (Credit: David Hookstead)

I’ve also encountered my first major problem. My cell phone is useless in Bar Harbor. No, I don’t mean reception is weak. I mean it’s nonexistent. Nothing. No internet, no messaging and no calls. I feel cut off from the world. A missile attack could be inbound, and I wouldn’t know a thing about it. Luke Fickell could be threatening to quit the Badgers, and nobody would be able to reach me. That had me anxious, but again, there’s nothing I can do about it.

With my phone being useless other than being a paperweight, I decide to lean into being off the grid and in an area where I can more or less come and go as I please. Much like my first spot in Maine, I feel incredibly safe in Bar Harbor. I left my computer in a coffee shop for 15 minutes while I went to check something out, and came back to it untouched. It would be stolen in a heartbeat in Washington, D.C. if I did the same thing.

Also, people are shockingly friendly. I know this is how most people behave in America, but it’s easy to get bitter and cynical after living in a big city war zone for so long.

I have two priorities:

• Explore a little bit
• Find good food and alcohol

I’m pleased to report that I did both. Now, I didn’t go to Acadia simply because I didn’t have the time, but I did check out plenty of different areas of Bar Harbor. I pretty much explored the entire island.

There are two things I really liked about it. First, there’s a land bridge to another island when the tide gets low. The walk is maybe a third of a mile, and while I didn’t walk the entire thing simply because the tide hadn’t gone all the way down, it was super cool to check out. If you’re ever in Bar Harbor, I suggest you give it a look.

A photo of the land bridge to a second island. (Credit: David Hookstead)

Second, the amount of history and massive estates on the island is hard to overstate. I walked around and saw plenty of houses that I couldn’t dream of being in as a kid. I’m pretty sure blue-collar guys like myself get shot if we try to walk towards a $10 million+ estate on the water. As for the history, the coolest memorial I found was to all the men who fought to save the island during a 1947 fire. Yes, you read that correctly. There’s a monument honoring the men who held the line against would-be island-destroying fire. I bet those dudes had plenty of gritty working-class guys among them.

A photo of the fire memorial. (Credit: David Hookstead)

Now, what’s the situation with the food and alcohol among some of the richest people in the country? It’s awesome. To be clear, I don’t really like seafood. I’m a red meat, chicken and potatoes kind of guy. I’d much rather eat steak or a burger over shrimp or fish, and I eat at least half a pound of chicken every single day. Yes, you read that correctly. I eat half a pound of chicken *EVERY. SINGLE. DAY.*

I figure when in Rome, you might as well act like a Roman. I have never had so much seafood in my life as I have since last Friday. It’s been nonstop shrimp, fish, lobster and any other seafood you can think of. There were even some oysters mixed in. I’ll also be honest with you when I say my stomach didn’t always handle it well. Turns out switching from red meat to seafood without any transition might not be the greatest idea. Do I regret it? No, I’m in the trenches now, and forward we push.

A look at the food! (Credit: David Hookstead)

(Credit: David Hookstead)

What about the booze situation? It’s elite, as you’d imagine. After all, we’re talking about an area of the country where billionaires own second homes and have boats docked all over the place. They expect fine drinks, and while I’m usually good with light beer, my fiancée convinces me to branch out a little bit. There’s one place I have to give a major shoutout to:

Cottage St. Pub.

Again, I’m not a cocktail guy at all. Most people who grew up like myself in the cold and brutal winters of Wisconsin prefer beer or straight dark liquor. However, I’ve embraced the unknown since arriving in Maine, and that’s not changing now just because I somehow snuck into another haven for the rich.

The cocktails at Cottage St. Pub are unreal. They had your classic cocktails like painkillers and such and then there were a dozen or so in-house specials you won’t find elsewhere. This is where the place thrives. It had a unique take on a spicy margarita that was borderline addicting. I’d admit how many I had, but there’s a slight chance my mom might read this. Sorry mom! However, that was only the beginning. There was a bourbon-based drink that involved fire, and on my last night, I knew I had to order one. I’m probably going broke no matter what at this point thanks to this trip. What’s another $15 down the drain? I hope you all realize how big of a deal this is for me. The idea that a guy from Randolph, WI would be in Bar Harbor ordering specialty cocktails that involve torches and fire is hilarious for me and anyone who grew up like I did. It didn’t disappoint. It was a shade sweet, but that wasn’t a bad thing.

(Credit: David Hookstead)

(Credit: David Hookstead)

(Credit: David Hookstead)

We also found ourselves having great conversations with people when we went. One night, there were two sisters from Florida that we traded stories with for hours on end. I could tell these were high class people. I don’t think they could tell I was a "pull yourself up from your bootstraps" kind of guy. Did little old David Hookstead manage to trick, not one, but two Maine high class societies that I might be one of them? It’s certainly starting to seem that way. I wish I’d gotten their names because they seemed like good people to stay in touch with. Another night, we met a guy who spends about half the year there and the other half in Texas. Again, I know high society when I see it, and while he seems to do a great job of shielding it, he lets the cat out of the bag when he mentions he went to boarding school in Switzerland. A tell sign if there ever was one. Also, this guy called Josh Shapiro not being the VP pick before seemingly anyone else in the country. Wild times.

What was supposed to be a short trip to Maine for one of the fanciest weddings I’ve ever been to, ended up turning into a hell of an adventure thanks to a canceled flight. Do I think I’ll ever be a part of high society? That’s a good question. I’m not even sure I want to be, but I was curious how a guy from the fringe class would be embraced by the American elites. Would they sniff me out from a mile away? Would I be welcomed with open arms? The answer is the latter. It turns out life among the richest people in America isn’t all that bad. Dare I say that I might have even enjoyed it? Should this be my new normal? I don’t think so. I’ll always be a regular guy at my core, but I won’t lie when I say I truly enjoyed my five days in Maine. It’s a beautiful state full of fascinating history and people. It was seven years between trips, and I’m definitely not going to wait that long again. I’ll also definitely prep my stomach a bit better for five days of nothing but seafood. Until next time Maine, thanks for making this blue-collar Midwestern American feel like an upper-class dude for just a few days.

Some random thoughts I couldn’t fit in elsewhere:

• There was a shocking amount of people speaking German in Bar Harbor. No idea why.
• People walk very slow. Is this normal for rich people? It was beyond frustrating at time.
• My fiancée’s ring had some women talking.
• Seriously, what the hell is up with D.C. being a war zone, but I didn’t lock my doors for five days in Maine?
• Take some time to drive through the rolling hills. It’s worth the time.
• The wedding I was at had maybe the best espresso martinis I’ve ever had. Yeah, I like espresso martinis. Get over it.
• Barely saw any overweight or out of shape people.
• Lots of American flags and Trump flags/signs.
• One of the bars we had access to was 100% on the honor system.

Let me know your thoughts on Maine and my experiences at David.Hookstead@outkick.com.