Chicago to New York City – Day One

Thursday, September 26, 2019

Start: Chicago, Illinois
End: Fair Oaks, Indiana
Mileage today/cumulative: 74 / 74
Elevation Ascended: 817′
Weather: Sunny, 59° at start; sunny, 71º at finish
Flat tires (entire group) day/cumulative: 1 / 1

We could not have asked for a better day to begin our ride to New York City. Perfect weather, beautiful views, and low traffic made for a very easy 74 miles. Our ceremonial start was at Buckingham Fountain in Chicago’s Grant Park and we all wore special Chicago – New York City jerseys that we purchased from Adventure Cycling. This seemed like the perfect spot for a group of baby boomers. The Fountain’s water capacity is 1.5 million gallons and depending on wind conditions, the major displays recirculate approximately 14,100 gallons of water per minute. The original pumps and motors are still in operation today. Old and still going, just like us.

Before we rolled out, Bev got some puppy love from an Irish Setter named Lady Bird, who happened to be walking her owner past our hotel. One of Bev’s goals for this trip is to “stop and pet all of the dogs” (her version of “stopping to smell the roses”), so I think it was a good omen that Lady Bird showed up to wish us well and be our good luck charm for the trip.

Our first nine miles were on the Lakeshore Trail, a beautiful bike path that runs along the shore of Lake Michigan. We eventually left downtown and made our way through Chicago’s Southside. The transition from beauty and inspirational views to decay and hopelessness was made even starker by nine white cyclists riding expensive bicycles past housing projects busy with police activity. It made me extra aware of my white male privilege.

Of the first 40 miles of today’s route, nearly all of it was on greenways and bike paths.  Once we got out of Chicago, every town had connecting bike paths that finally ended in Crown Point, Indiana. Along the way, we crossed the state line on the Pennsey Greenway, adding Indiana to the growing list of states we’ve cycled in. Our pace was relaxed all of the way into Crown Point, where we stopped for lunch. Once we left there, a few of us put the hammer down and flew to our hotel at Fair Oaks Farms, where there’s a nice hotel, a restaurant, and an odd dairy farm attraction that seems very disturbing.

At our group dinner, we ran out of superlatives to describe Day One. There will be difficult ones ahead but those can wait.