Bluey's Corner

Getting to the start (Part 1)

St. Paul, MN • 2026-08-05

In order to bike from New York to San Francisco, one must first be in New York. For various reasons, I wanted this secret first leg of the trip to be made by train. Unfortunately, because this is the United States, getting there is a three-day process.

The bike is treated similarly to a checked bag, but only certain services will take the bike without first needing to partially disassemble it to fit in a box. This is part of the reason why I’m starting in New York and not Boston.

Amtrak is often very delayed, which is why I put in a day’s layover in Chicago. I was also hoping that I could get a little more sleep this morning, since the train actually starts all the way back in Portland. Unfortunately, it was running right on time.

Woke up at 6 in the morning, gathered my things and took the light rail with my lovely boyfriend to get from his apartment to Union Depot in St. Paul. The bike got put in the baggage car, and then I said goodbye to the aforementioned boyfriend and my parents.

The train was pretty busy. A lot of Mennonites, as usual. I was too tired to really focus on much, and with neither a laptop nor earbuds I was pretty bored (especially once you get deeper into Wisconsin and looking out the window gets less appealing).

Train arrived on time in Chicago. I left my sunglasses behind, I think. I biked to the lakeshore for a little bit, then back through the city to a hostel for the night. Ate at a nearby Chinese place.

Tomorrow will mostly be free to go around Chicago. The train leaves in the evening and will go overnight and into the next night. Not looking forward to that one. Should be pretty, at least.

Route Map