My First Road Trip: Traveling for work, crossing the border, and solo travel tips!

Sometimes the universe gives you an opportunity that you just can’t pass up. When I was asked by my job to go on a 10 day/3 city trip, I was initially VERY nervous. I’ve never travelled for a job before, much less driven almost 2,000 miles for a trip. But for the past nearly two weeks, thats exactly what I did, and I was surprised at how much fun it was!
1 bookmobile, 2 countries, 3 cities: here’s a breakdown of the world’s weirdest road trip.


Getting to Toronto from Brooklyn was tough. One full day of driving got us only to Buffalo, NY, which is where we ended up stopping for the night. I was foolishly hoping that we’d at least be able to stop and see Niagara Falls while we were there, but by the time we got to the hotel I was so dead I immediately went to sleep. The next day we crossed the border, which I have never done via car before. I was so disappointed that apparently they don’t stamp your passport when you cross this way? I was really looking forward to getting a fresh Canadian stamp in it! C’est la vie.

Once we got to the city we immediately had to go and set up for our work shift, which required a lot of coffee for both myself and my coworker. We were in this absolutely beautiful area of town called the Historic Distillery District, which is all gorgeous old brick buildings that have been converted into shops, restaurants, and art spaces. I loved walking around there after my shift was done.

The inside of the Young Center for the Performing Arts,
where the production of Orlando was

I also got to walk around a lot in the downtown area and along Queens St, where there a lot of other shops. I remembered going to this amazing thrift store the first time I went to Toronto, so I hunted that down again (luckily it was still there after about 6 years!) and got some great vintage t-shirts. I also found a record shop where I finally picked up a copy of The Freewheelin’ Bob Dylan, a record that means a lot to me. I could write a whole other blog post about that one album, so I won’t bother to get into it now.

My last night there, I really wanted to see a show of some sort while I was in town because Toronto has such a great theatre scene. I was able to get same day tickets to Soulpepper’s production of Orlando, which was absolutely amazing. I walked away desperately wishing I could see it again, and now I’m on the hunt to get the book by Virginia Woolf to read. (If you know of any particularly beautiful editions of it, please send them my way!)


Me, trying to collect my emotions after the rollercoaster
ride that was Mamma Mia!: Here We Go Agai

From Toronto, we drove to Hamilton, Ontario to stay for 2 days. Our first day there was our only free day of the whole trip, meaning no driving and no work. Unfortunately, Hamilton didn’t have a ton to offer. Hamilton historically has been a city based around the steel factories, but it slowly on the up and up due to it’s community of artists. It’s nice the see a city switch from solely industrial to more community based, but it’s still sadly riddled with empty storefronts.

I did manage to find a town square section that had a pretty fountain and some gardens, and there was a live band playing all day. I liked getting the chance to just sit there for a few hours and read my book, people watch, and listen to some live music.

I did however manage to find a used bookstore where I stored FOUR Penguin Orange classics, which I collect. These are almost impossible to find in the states, so I was beyond thrilled to see those in the shop, and only for $20! At night I had originally hoped to see another play here, as there are some theaters around where I was staying, but none of them had any shows running (somehow???) so I naturally I went to the movies and saw Mamma Mia 2 instead.

Also when I was in Hamilton, I found this great graffiti alley that reminded me a lot of Clarion Alley in San Francisco, which is one of my favorite places in the whole city. It was great to get a taste of the artistic community in Hamilton and see what topics and issues are most important to them.


Getting to Chicago from Hamilton was also very arduous. After a full day of driving, we stopped over in Gary, Indiana, where the only thing near our hotel was a Denny’s and a liquor store. Naturally, we left first thing in the morning the next day. We arrived in Chicago just in time to check into our hotels and do our first shift of work down at the Hyde Park Art Center, which is a lovely place, but doesn’t have much around it. I ended up spending my free time more around the Logan Square neighborhood, where I was staying.

Chicago was especially great to stay in because I got to stay in an actual apartment! I was housesitting while I was there for a friend, who has a truly precious 3-legged cat named Logan that I immediately fell in love with. My other friend from high school named Gavin was also kind enough to show me around the neighborhood, where we went a zine bookstore that I could have spent a thousand years looking through.

Logan, the three-legged cat

My last day in the city I pushed myself to rally enough energy to go downtown, and I’m so glad I did! Lollapalooza was going on at the same time, so I was worried that everything would be so busy and crowded, but since I was walking around while the concert was happening, it wasn’t so bad. Chicago is such a beautiful city – all of the buildings have great Art Deco features, the parks are well kept, and the streets so clean! I could’ve spent a whole week there just walking around, and I definitely will have to go back someday soon to see it all. I got some pizza (not deep dish though, I honestly think that it looks disgusting), and miraculously found a place called Redhead’s Piano Bar. Piano bars seem to be a big thing in Chicago, because when I was looking on the map there was about 5 of them all near each other. I went in and was the youngest person there by about 15 years, but I still managed to make some friends and hear some good music (even if I didn’t get a discount for being a redhead ☹️).

Destiny was calling me with this sign, even if they wouldn’t give me a redhead discount

I somehow did not remember that a river runs through part of Chicago from my first trip here years ago, so I loved walking over the bridges and getting these beautiful pictures.
I didn’t even mean to end up here, I thought it would be too “touristy” for me to go but I’m so glad I ended up here anyway! Don’t ever let people tell you that something is dumb people it’s full of tourists, I loved seeing Cloud Gate aka “The Bean”.

Overall I am SO glad that I went on this trip, even if those days full of 10 hours of driving felt like they were never going to end. I managed to have a great time in every city, even while walking around by myself, which was most of the time. This is my second time traveling “solo”, even though the actual traveling part was done with my coworker. If you’re thinking of taking a solo trip, I’ve compiled some tips to consider while traveling!

1. Decide before you get there how you will get around.
Is the city your visiting one you can walk around easily? Is there safe and reliable public transportation? Does the city have Uber or Lyft that you can use? These are things you have to research before getting there, before you find yourself wandering around at night and unsure of ho you’re going to get back to your hotel.

2. Write down important addresses and phone numbers
Yes, PHYSICALLY write these down! If your phone gets stolen or dies, are you going to remember the exact address of where you’re staying? Especially if you choose to stay at an AirBNB, the address of where you are staying and maybe even the phone number of your host are important things to always have on you.

3. Don’t be afraid to talk to people!
It can be scary trying to talk to strangers when you’re alone in a new city, but I have had some of the best times while traveling alone because of friends I made at bars, restaurants, and theaters. The locals know all the good spots that are off the beaten track, so take advantage of that information!

4. Don’t do something just for the ‘gram
In both of my experiences traveling solo, there were often times where I felt like I HAD to do xyz because it’s what expected of a person on vacation, when in reality I was dead tired and just wanted to go back to my hotel. Your trip is about what YOU want to do, so don’t feel the pressure to go out and party hard every night if you actually just want to be in bed by 9.

Have you ever taken a solo trip or a road trip? How was your experience? Let me know in the comments!


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