First Steps West - Part 1 Cross Country Motorcycle Journey

First Steps West - Part 1 Cross Country Motorcycle Journey

There’s something both terrifying and exhilarating about committing to a cross-country motorcycle journey. After months of planning and preparation, the day had finally arrived to begin my adventure across America on my trusty SV.

Final Preparations

I finished up coaching my last MSF section at 1pm and headed directly to TonyJuliano’s shop. The final checklist was crucial:

  • Mount a fresh set of Avon Storms

  • Relocate rear turn signals

  • Wire up and mount the GPS

Tony, as always, was nothing less than a lifesaver. He helped me pack the perfect tiny tool kit to assist with anything the factory one might miss. I left his place around 9:30 PM and headed straight for York, practicing with my new Garmin Quest 2 along the way.

Moments Before Rolling Out

The Last Day Home

I spent my final day before departure at my pop’s house, where they threw me a proper sendoff cookout.Their mix of support and concern only fueled my determination.

Day One: York, PA to Madison, WI (900+ miles)

I snoozed right through my 6 AM alarm and woke at 7. Quickly repacking my belongings and throwing on my gear and rain gear, I finally hit the road. A light mist wasn’t the picture-perfect start I’d hoped for, but it wasn’t bad.

The first real break in the weather came 40 miles over the Ohio state line. The sky opened up enough for me to peel off the rain gear and catch a quick lunch. Back on the road within the hour, I picked up my brisk pace.

Good Samaritan Moment

Early in Indiana, I spotted an older lady stranded with a flat tire on the left-hand berm. Needing a break to stretch my legs, I pulled over to help her swap out her right rear tire. Changing it was unnerving at best - we were extremely close to very fast-moving traffic. I hoped a little good samaritan karma would help me out on my journey.

Chicago Challenges

The smooth sailing ended when I hit the Chicago Skyway. What a sight to see, but the expressway riding reminded me a lot of South Philly, just with more lanes. This is where my GPS showed its limitations - it couldn’t calculate or depict my interchanges quickly or clearly enough. To add to the challenge, it started to downpour with no easily accessible places to put on rain gear.

My first navigation error came when I accidentally chose Milwaukee over Madison, WI, ending up an extra hour and a half from my first destination.

Arrival in Madison

Final Preparations

I finally arrived around 9:30 PM at my friend’s (svroom13) parents’ house, where I’d be staying for the next two days. Despite the long day and weather challenges, both gear and bike held up great, though my GPS suction cup became unstuck in the heavy rain. No problem - I just tossed it in the top of my tank bag.

Madison Capital Observation DeckHamming it Up

Madison Discoveries

During my rest day in Madison, I learned some essential local wisdom:

  • Cheese curds are squeaky, and no one knows why (nor do they question it)

  • The Madison Capitol is gorgeous

  • Scott’s Pastry Shop is absolutely the bomb

In my pre-journey preparation, I only managed to forget two items:

  1. Razors to shave (easily fixed)

  2. My USB cable (required a trip to Best Buy)

The first leg of my journey was complete - roughly 900 miles down, and countless more to go. Madison would prove to be the perfect rest stop before heading west toward the Badlands.

Stay tuned for Part 2: Through the Badlands - Madison to Yellowstone


This is part 1 of a 5-part series documenting my cross-country motorcycle journey. Follow along as I make my way from Philadelphia to the Pacific Coast and back, covering over 12,000 miles of American roads.