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How I started with Amtrak

Kev’s First Amtrak Adventure: How It All Started

My first Amtrak adventure started on May 25. 2012, and it has changed my life. However, I wasn’t aware of that at the time. My Amtrak travels allowed me to see things I would never have seen, meet some fantastic people, and have experiences I never thought I would have.

Because of my Amtrak adventure, the train took me to places such as New Orleans, which I did not want to go to, but did so because I wanted to ride a particular train. Now, similar places have become my favorite places! On the other side, I also experienced imposter syndrome regarding travel.

I Did Travel Before This Trip.

My travel life breaks down into four phases, each a building block for the next adventure.

Amtrak California Zephyr
A view of Amtrak’s California Zephyr from my roomette

In phase one, from birth to eighteen, my parents taught me simple travel, like visiting family and day trips. But I don’t remember getting hotel rooms or trips like Disney. My paternal grandparents took trips when I was young. These are memories that have stuck with me!

Phase two started at age eighteen when I bought a 1990 Oldsmobile Silhouette and used it on many road trips and as a bike carrier for cycling tours. I learned to enjoy solo travel during this time, and that is something I cherish these days.

In phase three (twenty-five to thirty-five), I did not travel much but learned the basics of public transportation. Then comes phase four, which this article covers; it started with one train trip and ended with me traveling across the country.

In phase four, I have been on all but one (the Auto Train) of Amtrak’s long-distance routes, most of the Midwest regional routes, and coast-to-coast by rail and air. Phase four starts with this story.

Don’t Drive Down Here.

In 2012, my friend Pete moved to Chicago and invited me to an event we could attend and hang out at. He was kind enough to let me stay with him, but he had a caveat for my visit: don’t drive down.

CUS Enterance
Outside entrance to Chicago Union Station’s Great Hall

His logic was solid: parking in downtown Chicago is expensive, and parking by his place was a premium. I owned a 1989 Chevy Celebrity, not a tiny car, yet not the land yacht.

He suggested taking the train down, either Amtrak or Metra. Since I was coming from work, Amtrak became my choice because it was closer.

Pete took the train a few times before to share his experience with me.

I have driven to the windy City in the past, but the idea is stressful. On the other hand, I had never done anything like this before, but Pete assured me it was easy and comfortable, so I trusted him.

I did the research and booked my first Amtrak Adventure.

Since I decided to take the train, it was time to research, and that started with a visit to, where I found the Sturtevant Station. This station was a great choice because it was a reasonable distance from work, not too far from home, and had cheap parking.

Soon, I had the Amtrak app on my phone, signed up for Amtrak Guest Rewards, and booked my round trip aboard Amtrak’s Hiawatha.

With Pete as a guide, I would not get lost. At least, that was my hope. I have experience with mass travel in Milwaukee using buses, but the CTA is a little different.

I know where the station is; apparently, I didn’t

Front of SVT
A street view of the Sturtevant Station

The day of travel came, and I was ready for my first Amtrak adventure! My bag was packed and in the car, my shift at work ended, I was punching out for the weekend, and I was excited to head to Sturtevant.

Over the years, I have been through Sturtevant from home, but I needed Google Maps to get there from work. Now, I use the app until I reach an area I recognize, and then I turn off the GPS and go by memory. Great idea, right?

That was a mistake! I drove past the depot on a parallel road on the other side of the tracks, headed for the original Milwaukee Road station’s former location. The old station had moved to a park, and a Canadian Pacific Kansess City building is in its place. I don’t know why there was so much confidence; this was my first Amtrak ride!

So, I swallowed my pride, re-entered the station’s address in the app, and found the depot. After paying for parking and gathering my belongings, I headed to the platform, ready for my adventure.

Soon, an announcement came over the PA, and the passengers at the station gathered for the train. A few moments later, the train stopped at the platform and picked us up for our 63-mile journey to the Windy City.

All Aboard!

Hiawatha at SVT
A southbound Hiawatha pulling into the SVT station

Before boarding the Hiawatha, I had discovered another Amtrak newbie waiting for the train. So, between the two of us, we figured out what we were doing and when the train came. She and I climbed aboard and searched for our seats. We sat in a section reserved for those needing assistance, so we moved and sat back and enjoyed the trip.

The train had six coaches, and it was full but not packed. It took about an hour to get to Chicago. I loved the train’s motion and the sounds of the steel wheels rolling on the steel rails; it did something to my soul.

Watching the world go by was fun; before I knew it, the Chicago skyline appeared. When we reached Chicago, my travel buddy and I bid farewell and went our ways.

Chicago, Chicago, that toddling town.

CUS Great Hall
The recently restored Great Hall at Chicago Union Station

Looking back, it is funny that I got confused and overwhelmed with my first time in Chicago Union Station. These days, I know that station well and no longer find it confusing. After leaving the train,

Soon, I was up the escalator and out the door to meet Pete. It was time for Google Maps to guide me to Pete’s place of employment.

I liked the trip.

After a fun weekend, I headed home and felt like I had mastered Amtrak’s Hiawatha.

That year, I visited Pete four times via Amtrak. Little did I know that something happened to me on that first trip; the little wanderlust bug in my soul woke up again. Not only did that bug wake up, but it also likes train travel.

You might like San Francisco.

Ferry Building San Fran
The Ferry Building in San Francisco, CA

In late 2012, my friend Ben traveled to San Francisco, and after his return, he told me I might enjoy a trip there. Sometimes, people say something, and you ponder it in your heart for some unknown reason. I did that in San Fransico, which became my first cross-country destination!

Planning my first long-distance trip

My taxes were kind.

In February 2013, I worked on my 2012 taxes, and because student loan interest was tax-deductible (at that time), I found out I was getting a nice chunk of change back.

Parks and Recreation GIF

As Jean-Ralphio Saperstein of Pawnee, IN, would say, I was flush with cash (Parks & Recreation reference).

Maybe not flush with cash, but I had enough for an adventure.

I could have invested that money but decided to take a trip; I invested in myself, at least that is how it seems.

The time came to start planning and researching again, and I discovered that is something I enjoy.

I talked to Ben again, asking him a few more questions about the City by the Bay. Because I enjoyed my short train trips, I thought, why not see if Amtrak could take me there, and yes, it could.

What my research told me

My research showed I could start at the Sturtevant Depot and transfer to the California Zephyr in Chicago, where I would ride to Emeryville, CA, and then a bus to San Francisco.

I don’t want to say I am cheap, but happy not to pay retail when you don’t need to. So, in my research, I found NARP, the National Association of Rail Passengers. NARP is now the Rail Passengers Association.

After joining, I received 10% off the base rate of the tickets, and my membership fee covers close to the same amount of money I saved.

If I took any more trips, I would start saving, plus it is a good cause!

New Amtrak adventure: New Luggage

Since I had not traveled much, it was time for new luggage. My secondhand luggage was falling apart and impractical for this journey. Clueless about what was there, I turned to the big box and discount stores.

The hunt was for a 24-25″ rollaboard, which ended with a walk to the clearance section of my store (I worked at a big box store then). Someone returned their online order of a set of four suitcases that retailed for $119.

After I checked out and used my discounts, I purchased the four-piece luggage set for about $40; I kept the 25″ and the small hand carry-on bag and sold the rest to my mom, so $20 for what I wanted wasn’t too bad.

From my experience, I found it true that you get what you pay for with suitcases and luggage. I also learned that designer suitcases cost more but are often not much better than the cheaper ones, usually made by the same company. I am sure that is not always the case. Looking back at my first trip, I discovered I traveled too heavily because I brought a full 25″ suitcase plus a backpack!

The start of my first long-distance Amtrak Adventure

The day came for my Amtrak Adventure, and I was excited. My coach seats were booked, my bags were overpacked, and I made it to Chicago.

Beer and popcorn
Pre-travel comfort food, beer, and popcorn

Because of my excitement, I left early. I would rather wait at the train station or airport than at home.

By this point, I knew Chicago Union Station pretty well. I had my favorite places to eat and wait. One of those places I enjoyed was a bar off the Great Hall. (The bar closed, and I cannot remember the name.)

I often went there because they had good food, free popcorn or other snacks, and a nice tap and container beer selection.

Side store: While at the bar, I often dealt with self-doubt before the trip and contemplated if I should be traveling. Can I cancel it now without losing too much cash? I would remind myself that it is okay for me to travel.

After a few drafts and bowls of popcorn, I had to get ready to climb aboard the California Zephyr.

California, here I come; a new Amtrak Adventure is underway!

My seat was behind the center stairwell on the train. I had a female seat partner from one of the Scandinavian countries visiting the USA. If I remember correctly, she was on her way to meet with her boyfriend, who met her in LA after visiting the Bay Area.

This video is of the first Amtrak long-distance train I was on!

After the train left Chicago, I walked to the Sightseer Lounge car, found a seat, and started chatting with a gentleman from Canada.

While riding down the rails, the dining car steward came through the car, and I decided to treat myself by making a reservation for dinner in the dining car. After some time, the dining car steward called my dinner reservation time. Since I was in the Sightseer Lounge car, I did not have to walk far because the dining car was next.

When I entered the car, I was seated with three ladies; two were a couple from San Fransico, and the other was another solo traveler. After we sat down, I asked if they were all from the United States, and they looked at me and said yes, but why? I told them they were the first US citizens I chatted with on the train besides the staff. We had a nice chuckle, and it broke the ice. The City by the Bay ladies gave me some excellent tips and hints.

Later that year, I wanted more Amtrak Adventures.

A few things happened on my first long-distance Amtrak adventure; I fell in love with the views, the pace of train travel, and the people who made my trip fun. All of these made me fall in love with train travel.

After that first long-distance trip, I had train travel withdrawals, and I wanted more. I found Amtrak’s Midwest Corridor, and there were several places I could go for day trips.

Amtrak's Capital Limited
Capitol Limited at a station stop in Cumberland, Maryland

The furthest destination I could go in a day was St Lois, MO; the closest was Milwaukee. I needed to learn a new skill: how to ride Metra. By the way, it is not hard.

Metra could take me to Chicago earlier than the Hiawatha, allowing me time to get coffee or breakfast and catch early trains. Plus, Metra is cheaper.

Tuesday became my train day, and I rode a train on that day or at least once a week for years.

One big trip for the year was not enough for me, so I booked another long journey to Washington, DC, this time. The trip was another coach trip. I took the Capitol Limited to DC, stayed at night, and took the Cardinal home.

Why am I telling you about my Amtrak Adventures?

I am not trying to brag, but I want to let you know that people make mistakes and that travel is a skill you learn from and grow.

Kev Aboard the Hiawatha
Riding the mighty Hiawatha to Chicago

I loved watching cooking shows as a kid and remember watching Yan Can Cook. His philosophy was simple: if I can cook, you can too, which is my philosophy with travel.

I am a regular person; if I can travel, so can you.

When I started traveling, I was nervous, as I am sure you may have been.

My nervousness almost got me on a few trips, but I fought through the anxiety. Fear and worry can lead to regrets, and you can miss out on a lot. (I am sympathetic to those with crippling fear.)

There is more to this story, and I plan on sharing that with you in another post. This is how I got started, and maybe now is a good time for you to begin your travel story.

If you want to start your Amtrak journey, click here to start your research on riding Amtrak.

Safe Travels!


Kevin Monteith

Kev Monteith has been traveling on Amtrak since 2012. With over a decade of experience, he has been on over 800 trains, covering over 200k miles of rail. Kev enjoys helping others achieve their travel dreams by providing support and information. Outside of travel, Kev enjoys making music as an organist and outings with family.

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