Chapter 2: Midwest cities

Canandaigua, NY --> Detroit, MI --> Chicago, IL || July 4th - July 8th

Hello! We’re back with our second post. 

We arrived in Detroit on the evening of July fourth. It was a long, windy drive through Ontario, Canada. We spent most of the time talking, thinking out loud about the world, what a real multiracial community could or should look like, how few examples there are in America, how we’d like to be a part of one. Along the way, we attempted to see Niagara Falls on the Canadian side, but it was too packed! We caught a glimpse from the car and decided that was fine.

The ride culminated in a long, underwater tunnel from Windsor Canada to Detroit, Michigan. The tunnel traffic was accompanied by googling how underwater tunnels are even made?? 

We pulled up to the Detroit Foundation Hotel and the valet attendant, seeing our car packed with things, jokingly asked “are you driving across the country?” After a chuckle and enthusiastic “yes!” we headed inside to the bar for a bite to eat. Ironically, our bartender, the first person we chatted with in Detroit, was from Allston, Massachusetts. 

The next day, we explored the Detroit Riverwalk and went to the Charles H. Wright Museum of African American History. Its main exhibit, “And Still We Rise” is set up as an immersive timeline where you begin in early civilization in Africa and end in modern day Detroit following the experience of Black people who were enslaved and transported to America. Anyone in Detroit or visiting should spend time here. It presents the facts of our history without stripping our agency or making it all too painful to engage with. There were so many stories of rebellion, survival, leadership, and bonding together in the fight for freedom that I had not known.  

Charles H. Wright Museum of African American History; Detroit Riverwalk

After less than 24 hours, we were back on the road to Chicago. Once there, we stayed at a conveniently located though poorly decorated airbnb for a few nights while I worked my final days at Bridgespan. Alongside wrapping things up, we made time for some fun, thanks to my dear friend Emma’s Chicago recs and my former colleague and friend Maggy making the time to see us! Some highlights: 

Running on the 606 - a Highline-esque running/bike trail for six miles through the city.

Brunch at Lula’s cafe. Amazing breakfast burrito plus they had an Early Grey Snickerdoodle cookie, which I didn’t even know was possible but if you know me - those are my two favorite things in one.

Architecture River Boat Cruise — beautiful way to see the city from the water!

Blues at Rosa’s - cozy venue where we heard young and old, Black blues singers. It was SO fun. We danced, laughed, made friends with the handful of older Black Chicago people who all seemed to be regulars at this spot. They were so excited we had made it all the way there from Boston and a few had tales of their own to share about visiting Boston ‘back in the day.’

Hanging with Maggy & Henry! A very fun part of this trip we began to realize was seeing friends along the way we rarely get extended time with.

The only downside of Chicago was that we got our bikes stolen. (But…Cole came up with a plan… stay tuned). 

Next up – Chicago —> South Dakota!