Roadtrip USA: Coast to Coast Adventure

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A California Kid Headed for The City in the Ultimate Roadtrip

Ahhh road trips. Whether they are short or long, there is something about packing up a car with friends or family members and taking to the pavement for a weekend journey or week-long adventure. Hours spent on the road give way to some of the best memories. Every friend group has their own version of their ultimate roadtrip DJ, ensuring an all-out jam and dance session to horrible songs of the 80s and pop of the early 2000s. It’s also a time where the seemingly endless white lane stripes and changing landscapes encourage your brain to fall into deep thought as time passes.

Don’t think twice about taking the road trip of a lifetime. I sure as hell didn’t. Two short years ago my best friend Nate and I decided to pack a Toyota minivan to the brim with all our belongings and ditch our childhood home in Southern California. Destination: New York City.

What to know before setting off on a roadtrip

Sure we could have got rid of most of our things and booked a flight but where’s the fun in that? Instead, two dudes in their early 20’s decided to take the ultimate road trip across the United States in a vehicle that had over 200,000 miles on the engine, no hubcaps, no back seats and seatbelts that didn’t work. Did I mention it had no airbags either? If we had enough balls to wake up one day and move across the country with no plans, a car not quite up to safety standards was not going to get in our way.

One piece of advice I would give to anyone road tripping across any country is to completely let the course play itself out. We had no plans whatsoever on how or when we would get to New York and that was what made the trip so special. We filled up the tank, said our goodbyes and peaced out from the west coast.

Did you know? – Depending on your route, driving from California to New York spans 3,000 miles and would take nearly 45 hours if done in one haul!

Roadtrip Changing Plans

The good ol’ American Route 66 was our initial plan but boy did things change. By the end of the first day of travel, we reached the South Rim of Grand Canyon National Park. We decided our first epic memory would be to catch the sunrise over the iconic geological wonder.

I grabbed a couple of sweatshirts and passed out on top of all our belongings in the van cabin while Nate laid across the two front seats for one of the most uncomfortable nights of sleep ever. Safe to say we planned very little of any this.

A few hours later we woke up to the pounding of rain on our van’s windshield. Operation sunrise was out so we waited for the rain to stop and hiked the cliffs for an unforgettable experience by midday. The rest of the day was filled with exploring the park as we ran into several packs of wild animals and even discovered a burnt forest.


The span of the next two days entailed the dry and rocky roads of the southwest. Away we went through Arizona, New Mexico and Texas before driving through Oklahoma City and finally arriving in Stillwater (where Nate is originally from). We checked out the small college town and managed to make it on OSU’s football field by acting like student workers.

After several days of sleeping in a van, it was nice to freshen up with a cold shower and sleep on a cheap hotel mattress. We really limited spending and booked a room only twice throughout the trip.

Rad Tip of Oklahoma: Be sure to check out Eskimo Joe’s in Stillwater, OK. It’s the go-to spot for massive eats and flowing drinks. One of the best college bars there is around!

Kansas City

After petting a horse or two, drinking at the local bar and seeing Nate’s childhood home we headed up through the midwest. I had played baseball in Kansas and Missouri during my college days so we were fortunate enough to stay with some friends along the way. Wichita, Topeka and Kansas City were all exactly how I remembered them – a bunch of skyscrapers in the middle of nowhere but it’s always nice to experience a different speed of life.

We met up with some old pals, drank a bunch of rye whiskey and headed to Top Golf in KC. Whether you are a golfer or not, this is hands down one of the best spots to go with a group of friends. It’s a multi-level sports bar bumpin’ great music and serving awesome drinks while you take aim at targets on the range. Midwest disc golf courses were pretty rad as well.


We then headed northeast to some major cities neither of us had been to before. Chicago was the first spot and it definitely did not disappoint. We grubbed on some local eats downtown and bought Cubs tickets for $13 later that night against the Pirates. As a die-hard baseball fan, this was truly an epic cross off the bucket list. Wrigley Field was stunning and I had never seen a crowd so enthusiastic about their home team.

The stadium was sold out on a Monday night in August. We grabbed a beer and a hot dog and sang our hearts out to Take Me Out To The Ball Game under the humid Chicago night sky.


It was then on to Cleveland for the sole fact to see the corner of St. Claire and E. 99th St., the intersection that birthed the legendary group Bone Thugs-N-Harmony. Hip-hop fans you know! The next destination was spent in downtown Pittsburgh where plenty of local bars had surprisingly great energy for a late-summer weeknight.

After a long day of traveling and bar hopping, we found ourselves in the Strip District hungrier than ever. We stumbled upon Primanti Brothers, a classic grubhub serving some of the most satisfying sandwiches on the planet. Signed memorabilia from celebrities and sports stars lined the shop for a true old-time feel.

Rad Choice: Double Roast and Cheddar – half pound of roast beef, double cheddar and parmesan horseradish mayo sauce


It was then on to Baltimore for a quick stop at my aunt’s house and a long-awaited shower. We both had been to D.C. so we skipped town to Philadelphia for one of the best bar scenes there is in sports.

As a big-time Eagles fan I was already stoked enough to see Lincoln Financial Field in person but what took it to the next level was Xfinity Live located in the Wells Fargo Complex. If sports are your thing, this is a go-to destination whether you are a Philly fan or not. It is the premier entertainment destination with a total of five massive bars that are interconnected for the ultimate party experience.

Rad Tip: If you happen to be in Philly during football season make sure to hit up Xfinity Live during or after the Eagles game. It gets NUTS..

Arriving in NYC

The final destination was our landing point that we had planned seven days prior. A week’s worth of incredible memories and new experiences had all lead up to this point, yet nothing quite compared to the feeling of seeing the Manhattan skyline as we crossed over the Verrazano Bridge into Brooklyn for the first time.

I remember how silent we both were as we took in the distant lights of the city. It was a bittersweet moment as we knew that our week-long journey was officially coming to an end. A new life, new home and new memories awaited us on the other side of that bridge.

We both can agree that it was by far the best week of our lives living in the moment and traveling to places that we had never been to before. It was truly a coast to coast trip of a lifetime that couldn’t have played out in a better way..

My Next Rad Roadtrip – Drive from Shannon to Dublin and play golf on as many Irish courses as possible. What’s yours?

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Harry R Bennett III

Harry R. Bennett III is a Los Angeles native who grew up addicted to playing sports. His love for the game of baseball eventually landed him several scholarships to play college ball across the United States. After receiving his B.A. in journalism, he pushed himself out of his comfort zone and moved to New York City in an effort to pursue his passion in the sports industry. Bennett has worked with major companies such as Fox Sports and Major League Baseball and has written for several online publications covering a variety of sports content. Although his playing days are over, he enjoys the endless pursuit of competition from athletics and action sports. In his free time, Harry can be found surfing, snowboarding, golfing, playing basketball and selling homes in Brooklyn. Follow him on Instagram @hb3_estates


    One thought on “Roadtrip USA: Coast to Coast Adventure

    1. Sharon Cotal says:

      Great article! Very fun and informative!

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