Entreprecurious

This past April, my buddy Matt Glazier a.k.a. Matty Leftovahs (of the infamous Roman Restaurant Bible) called me and asked if I had any interest in going on a road trip of epic proportions. 8 days of driving around an unexplored part of the country, taking in some great nature, and eating at the best local joints with one of my best friends from home? Sign me up.

I feel like the quintessential cross-country roadtrip is something I’ve often talked about but never actually done, so I was super excited. As the saying goes, this trip was about the journey, not the destination–and the journey started months ago when we brainstormed our route and places stop along the way. We settled on an itinerary that started in Chicago and ended back in Madison, would last 8 days or so, span some 3,307 miles (53 hours of driving), and bring us to places across the Mountain West that we’d always wanted to see. From there, we split up the remaining logistics. I was in charge of car details, and planning the Boulder and Yellowstone portions of the trip. Glazier was in charge of Cheyenne, Big Sky, and Jackson. And we would share the restaurant planning responsibilities–perhaps the most important part of the trip, and thus the most exhausting topic of research.

Chicago, IL

2:30 am: The Roadtrip Begins

The road trip starts off at 2:30 am when we decided we were too restless to go to sleep, and would just rather be on the road already. Obviously I was going to be the MVP of the trip, and in true MVP style, I took the first driving shift as Glazier slept peacefully in the front seat. Before we knew it we were in…

 

 

Omaha, NB

Lunch at Dixie Quicks

Dixie Quicks proudly boasting Guy Fieri at the front of the restaurant

No offense, Omaha, but there just isn’t much goin on there. The only reason we stopped there was because a) it was on the way, and b) Omaha is home to Dixie Quicks, as featured on Food Network’s popular show Diners, Drive-ins, and Dives. It didn’t disappoint. In fact, this was one of the better meals we had on the whole trip. Glazier had a ridiculous omelet with brie, green apple, and bacon. The tart green apples were julienned, which was a great touch, and cut perfectly into the creamy melted brie, and the whole thing was rounded out with the smoky thick-cut bacon. I had the cactus scramble simply because I’d never tasted cactus and was curious. It tasted sweet and vinegary, and went well with the black beans perfectly cooked eggs, which I then wrapped in the warm corn tortillas. The biscuits were also perfect–flaky, warm, homemade, and obviously slathered with butter. Great start to the trip. Thank you for that, Omaha.

 

 

Boulder, CO

Dinner at Mountain Sun

Another 8 hours of driving and we crept up on Boulder just as the sun was melting into the mountains. If you haven’t been to Boulder, please go. It’s got a bit of everything–the youthful energy of a college campus, great food, great beer, great music scene, and a friendly and perfectly quirky population. It reminded me a lot of Madison and Austin. We met up with Sam and Lindsay, my longtime friends from home who have been living in Boulder since graduating from college. We started off with a great meal at Mountain Sun, which is known for its great beer and burgers. Glazier got a great burger with bacon, cheese, sauteed mushrooms and onions, and a roasted garlic mayo. I got an awesome portabella mushroom burger and we split the blackened chicken quesadilla.

Breakfast at Lucilles

We woke up and went to Lucille’s for breakfast. Best meal of the trip in my mind. Glazier got the blackened salmon special which came topped with 2 perfectly poached local eggs. I got the special omelete with fennel sausage, zuchinni, and pepper jack, topped with cinnamon syrup. The biscuits were the best I’ve ever tasted. The side of cheesy grits was absolutely unreal. And to top it all off, homemade catsup, pepper jam, and blueberry jam. Literally one of the best breakfasts of my life.

Hike at James Peak

me overlooking the lake atop the James Peak trailhead in Rollinsville, CO

It was time for a hike. The James Peak trailhead at the Moffat Tunnel opening in Rollinsville, CO was where Sam tipped us off to. A little off the beaten path (about a 25 minute drive from Boulder), but completely worth it. It was a Monday, and we were the only ones on the trail. We were told it would take us 5 hours roundtrip, but athletic specimens like Glazier did it in under 3 hours of actual hiking. The trail took us through the forest and up a mountain, ending at a pristine lake all to ourselves. We sat for a bit, played some music, and went back down. The air was thin, but really we were just out of shape, so it was an exhausting but worth it start to the day.

 

 

 

Movie on the rocks

The Goonies at Red Rocks

Every Monday night at the famous Red Rocks Amphitheater, they invite 2 local bands to play during sunset and then roll out a gigantic screen and play an epic classic movie. We were lucky enough to be in town when they played The Goonies, one of my all-time favorites. I had heard about Red Rocks for years, and the Dave Matthews Live at Red Rocks is one of my favorites, so seeing it in person was a dream come true. It lived up to the hype, though. Really an absolutely beautiful place to take in a show. Great acoustics and just a ridiculously good looking setting with huge red rocks on both sides and a view of downtown Denver in the background.

 

 

A Fork in the Road of Life–sorry to get poetic on you

I found out that night that I got the job in NYC I’d been hoping to get. What a boost to an already amazing trip. We had jokingly said going into the trip that the purpose of the trip was for Glazier to talk me out of moving to NYC, but clearly now this was the move. Sorry Madison. I love you and the last 6 years has been amazing, but I’m moving on.

Cheyenne, WY

The road trip was off to an awesome start, and already it felt like we’d done a week’s worth of stuff in just over 24 hours. So that Tuesday morning we packed up our stuff (including our newly purchased cowboy gear), said bye to our friends, and headed north to Cheyenne, Wyoming. Turns out Cheyenne is only a 1.5 hour drive from Boulder, and after a 16 hour drive, I felt like I could crush a 1.5 hour drive in my sleep.

Frontier Days

Glazier and I outside the rodeo in Cheyenne

 

Originally Cheyenne wasn’t even on our itinerary–there’s practically nothing to do in that town. But to his credit, Glazier came across the fact that every summer Cheyenne is home to the Frontier Days fair. Country music, rodeos, bull riding, 8 pound turkey legs, and lots of beer. Sign me up. I had never been to a rodeo before, but let me tell you, it’s a fucking site to see. You haven’t lived til you’ve seen a cowboy chase down a steer, lasso it’s horns, dismount his horse at 40 mph while the steer’s neck spaps back in a flash of violence, pile drive the beast into the ground, and tie it’s legs…all in under 14 seconds. Watch this crazy video below to see what I’m talking about.

 

 

 

So after a long day of drinking Coors and rodeo activities, we went back to the hotel for a quick nap. We woke up and started back on the Coors train like true champions. It was back to the stadium for tonights’ event: bull riding. The only thing more entertaining than watching guys try to stay on a clearly pissed off 800 pound bull was the crowd in the stands. Needless to say, we stuck out. We couldn’t tell people we were from Boston, so we picked the most neutral place imaginable–Kenosha, Wisconsin, and went with that.

glazier crushing the turkey leg

After some good bull riding, it was time to hit the country bar. I watched on in awe as these country folk busted out seemingly choreographed dance moves worthy of So You Think You Can Dance. We made friends with everyone, bought them beers, and answered questions about what it was like growing up in Kenosha, Wisconsin. “I remember those frigid winter days on the farm helping dad keep the cows warm like it was yesterday,” I would tell them. I met one of the bull riders’ mothers. Apparently her son is #8 in the world. She demanded that I Facebook her son on the spot. It’s been 20 days and the friend request is still pending. The surprise of the evening was how good the food was. The corn dog was battered to perfection, and the funnel cakes were greasily delicious. But the winner of the evening were the slow-smoked turkey legs. These things were HUGE.

The day came to an end with me begging every employee in sight to let me take home their staff t-shirt as a souvenir. No such luck. I’m still salted about that.

Lander, WY

Lunch at Gannet Grill

great pizza at Gannet Grill in Lander

So we wake up Wednesday morning and crush out of Cheyenne early. ***Note to all interested in doing a roadtrip: leave early in the morning on days of long driving. It sucks waking up, but you’ll be so happy you did when it’s over. If you’re tired, sleep in the car–it’s more productive than sleeping in bed.***

We decide to disregard Google’s suggested route, and instead opt for a more scenic route that our friend Martin tipped us off to. This one brought us through Lander, MT, a “quintessential mountain town,” as Martin put it. We had an unreal meal of brick-oven pizza with chicken, garlic cream and bacon at the Gannet Grill, followed by a great cup of coffee at the local coffee joint. Great tip, Martin. (Martin would later come up huge again on several fronts…MVP of the trip?)

Somewhere 15 Minutes Outside Lander, WY

Casino stop

made $9. #winning

Glazier and I decided from there on out to say “yes” to everything for the remainder of the road trip. Accordingly, when we passed a little roadside casino on our way out of Lander, we stopped…and I won $9. Great little afternoon we had there.

Dubois, WY

sure are opportunities at the opportunity thrift store in Dubois

Sticking with our commitment to say “yes” to everything, we just had to stop in Dubois when we saw what appeared to be an absolutely epic store–The Opportunity Shop Thrift Store in Dubois, WY. I mean, I had no idea what the hell they meant by “opportunity,” but I was damn sure intrigued by this. We ended up making out like bandits. I got 3-4 epic Wyoming t-shirts, my favorite of which was the 2004 Dubois, WY D.A.R.E. program shirt. We also got a $10 grill, which we intended on using in Yellowstone…until it didn’t work. More on that later. And to cap off the experience, we got 10% off our monstrous $20 bill just by liking them on Facebook, which I conveniently did right there in the store on my iPhone.

We said goodbye to Dubois and headed out through the Tetons and Yellowstone en route to Big Sky, MT.

Big Sky, MT

they call it Big Sky for a reason

They call it Big Sky for a reason–the skies are fuckin’ huge! I think it’s just cuz there are obviously no buildings and the mountains look so distant that the sky just opens up forever above. Anyway, we’d heard about Big Sky as having some great hikes, good golf, interesting food, and friendly people. Check, check, check, and…check. So even though it was realistically a bit out of our way as far as the route was concerned, we felt like we had to check it out. And I’m sure glad we did.

Dinner at Bucks T4

Red deer with truffle risotto

We got tipped off by Glazier’s buddy that we had to go to Bucks T4 for dinner. I was a bit put off by the name, but was willing to overlook it as soon as I saw the menu. This place was IT. Neither of us were dying of hunger, so Glazier starts off with the summer watermelon salad. Let me say that this yellow watermelon was literally the most delicious watermelon I’ve ever tasted. Topped with some red onion and citrus vinaigrette–it was great. He made fun of me for my “boring selection” of the house salad, but this was no ordinary house salad–the cinnamon roasted pumpkin seeds and the cherry vinaigrette were so good that I neglected the fact that I am allergic to cherries (I would survive in the end). Really, the highlight of dinner was the red deer with truffle risotto, which we split. Neither of us had had red deer before, but it was surprisingly tender, lean, and ridiculously good. It came rare, with port wine butter sauce slapped all over the truffle risotto and fresh asparagus. Probably my third favorite meal of the trip.

We asked the waitress where to go hiking and she immediately snapped back with “go to Lava Lake. You won’t regret it.” So we decided to wake up super early and do it up before our round of golf at 11:30. We got back to the hotel where Glazier passed out immediately while I watched an episode of Locked Up Abroad. I set my alarm for 6:30am. Tomorrow would be a long day.

Hike at Lava Lake

Lava Lake in Big Sky

It was now Thursday morning, Day 5 of the trip. We were going strong, which was good because today would be the most activity ever crammed into a 16-hour period. We awoke at 6:30 that morning, and set off to crush Lava Lake. I especially liked the concierge’s directions to the lake: “Head about 15 minutes up-canyon, pull a U-turn at the crik (they pronounce ‘creek’ like ‘crik’), and park near the river. It was the most physically challenging hike of the trip, but again, we are athletic specimens, so equipped with an Albuterol inhaler, we ascended into thin air. It took us about an hour 15 to get through the dense forest and up to the lake at the top, where we were both out of breath. But holy shit was it worth it. This was the best hike of the trip.

Look at that view! Seriously. Unreal. We hung out for a half hour shooting the shit and talking about how we both used to be fat. Then we argued over who was the better Fatlete (Fat Athlete). I conceded the Fatlete award to Glazier, but only after he conceded that people liked me more when we were both fat (and probably still do now). That’s a tradeoff I’m happy to make.

Golfing

calling my shot...right into the weeds

There was only enough time to pound a burrito before our 11:30 am tee time at Big Sky Country Club. It was pretty expensive ($110 w/cart and clubs and balls), especially for me who doesn’t like golf that much. But it was literally perfect outside, so I figured what the hell. It was actually a ton of fun. We bet on who would win more holes. The stakes? Loser buys all the meat to grill when we camp out at Yellowstone. Glazier won, but he was on performance enhancers–kid was packing lips all round. He also went to private school, so he’s been surrounded by preppy golfers his whole life. I, on the other hand, went to public school because the $200 million Newton North (most expensive public school in history) was good enough for me.

Fly Fishing

fly fishing in Big Sky with Martin and the family

Hadn’t ever been fly fishing before, but when our friend of a friend Martin told us he’d take us out for a sunset fly fishing session with his son and wife, how could we say ‘no?’ So we put on whatever we thought fly fishers would wear–hiking boots, shorts, sweatshirts, and lots of bug spray. Now I had no idea what to expect. I had always thought that it was called “fly fishing” because of the something that had to do with the way they cast the line out. Wrong. It is because the bait they use looks like flies.

Also surprising was that the fish you are going for are like 1 pound striped trout–not exactly the “big catch.” That said, it’s more about the relaxation and zen-like flow of casting the line out into the stream. So I stood alongside the banks and froze my toes off in the water for 3 hours focusing on my breath and watching the sun melt into the mountains overlooking Big Sky. It was pretty meditative, actually. And guess what?! Right at the end, we both caught little stripers. What an end to the day. Plus, we made great friends with Martin and his family. They were amazing. When it was all over, we all went out to a great dinner, too…

Dinner at Corral Bar

If want a quintessential burger join in Big Sky, look no further than the Corral Bar. This place just runneth over with a classic mountain west vibe. Friendly people and laid-back bar area are the perfect setup for an awesome meal. Glazier got the buffalo burger, which was awesome. I got the sirloin steak. I just needed a steak, even if it wasn’t what they were known for. We ate and talked with Martin about his hunting hobby, which ended in him insisting on giving us pounds and pounds of red deer leftover from his last hunt. He shot the deer himself, gutted it himself, and then had a local butcher come over and package the fresh meat. We obviously took him up on the offer. This would become our dinner both nights at the campsite in Yellowstone. Unreal. Martin for MVP.

Pony, MT

ATV riding

Glazier atop his ATV at the cabin overlooking Pony, MT

Pony, MT is an old gold mining town that is all but a ghost town. Why go 1.5 hours out of our way to stop here? Glazier has a friend named Chip who’s family is a part-owner of a farm in Pony where they have some badass ATVs. So Chip arranged for us to take the ATVs out for a spin around their property. I had never been on an ATV before, but I’ve heard they can crush through absolutely any terrain. Still, I was a bit frightened because like a motorcycle, you’re not strapped in to anything. Plus, we didn’t have helmets. But Lezlie, the farm’s caretaker, assured me that her “13 year old daughter takes them for a spin all the time.” If a 13 year-old girl can do it, I figured I’ could, too. I was only sort of correct on this one.

About 15 minutes into the event, I was scaling up a steep grassy hill when I accidentally ventured slightly off the beaten path, hit a big bump, flew up on right my right 2 tires, and literally came within inches of bailing the vehicle, completely totaling the ATV. At the last split-second I was somehow able to gather my balance and come to a stop. I don’t know who Lezlie’s 13 year old daughter is, but these things are dangerous beasts that sorta scare the shit out of me. The video below is moments after the event. I could laugh about it when it was over, but I won’t be running out to ride ATVs again any time soon.

But the ATV scare was worth it when we got up to the cabin that overlooks all of Pony. It’s owned by the farm and the view is just spectacular (see picture above). On the way down, though, there were more challenges to come. First, Glazier’s ATV died while scaling up a hill. We had to ride 2 people on 1 ATV, which isn’t the most comfortable thing in the world when you’re driving over big rocks, deep ditches, and through muddy swamps. Then, Glazier led us off-trail. He claims to be so good at directions, but he was straight up wrong this time. Following his lead, we tried to go back to the farm straight through a swamp. The ATV got stuck 3 times, each time having to be pushed from behind by someone ankle-deep in mud as the ATV’s tires kicked up grime in their face. We finally got back to the main road and coasted back to the farm. On the way, though, we stopped dead in our tracks as a huge moose ventured into the road. 30 yards separated us from this beast and Glazer and I looked at each other like “what the fuck do we do?? Is it going to charge at us?” So we sat there staring down this moose for a good 30 seconds–an eternity when you’re wondering if an 800 pound animal with antlers is going to attack you. Alas, it scampered off into the woods, allowing us to proceed home with caution. Good times, good times.

Pony Bar

In need of a drink after my near-death experience, we headed to the infamous Pony Bar. If you could imagine what a bar in the middle of a Cowboy ghost town looks like, this would be it. $3 beers all the time, a couple pool tables, and homemade jerky were the highlights. They also had an amusing sign that read: “Please don’t throw your cigarette butts in the urinals. It makes them wet and difficult to smoke.” Classic. We headed out from there to Bozeman, MT to pick up our deer meat from Martin. From there we would head straight to Yellowstone.

Yellowstone National Park

this buffalo stopped in the middle of the road through Yellowstone, holding up traffic for 30 minutes

10 notes on Yellowstone:

1) It’s massive. It took us 2 1/2 hours from entrance to entrance.

2) Accordingly, things are not close by. Old Faithful is an hour’s drive from the canyon, for instance.

Glazier tries to move the beans with our impromptu spatula--a snow brush

3) Book campsites far in advance.

4) It gets freezing at night, even in the heart of summer.

5) Don’t try to plan your activities in advance–there are too many to choose from. Get there and tell a ranger what you wanna do, then they’ll guide you.

6) Old Faithful is a waste of time. See video below for an exact replica.

View from one of the trails at the canyon

7) The canyon/waterfall is amazing. Our best activities at Yellowstone are canyon-related, especially “artist’s point.” And look how close you can get to the 350-foot waterfall (video below)!

8) There are legit so many different landscapes there from desert, to tundra, to forest, to meadows, to plains, and everything in between.

9) Buy stuff before you enter the park, especially firewood–it’s a ripoff inside.

10) If you’re gonna do Yellowstone, do the Tetons as well (more on that later).

Tetons

The Tetons were unbelievably beautiful, and perhaps even more visually stunning than anything we saw in Yellowstone–especially Old Faithful. So we decided on our last day of the trip to go for a little canoe across Lake Jenny in the Tetons. It was a pretty peaceful place to brainstorm menu items for our 2-bite sandwich bar concept in Manhattan. If we’d had more time here, we’d have gone for some hikes–which I heard were epic.

Jackson, WY

The last stop on the trip was Jackson, WY, where Glazier’s friend’s family part-owns a ranch and golf club. This is where my storytelling ends, however, as I spent only one quick night here before taking off back to Madison in the morning–an 18 hour driving extravaganza that I was less than looking forward to. Part 2 of this post will be about my trip back and ultimately my trek back East to start phase 2 of my professional life.

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