Yesterday wasn’t just a winter wonderland in Chicagoland, it was the annual Shepley CTA Christmas Train ride.
This year it was just the Oldman and his two boys. Hazel skipped out, tucked deep in that preteen “Dad-is-embarrassing” phase. PopPop and Grampa Don rode along in spirit, and I’ll admit there was a moment when that hit me square in the chest.
The snow gave the day a magical touch, and per Don Shepley tradition, the lessons started early. The drive to Harlem/Lake was part defensive-driving class, part master class on dealing with idiots who still drive like the roads are bone-dry. Some people will never learn that snow doesn’t lie.
Up on the platform, young families bundled up with strollers, all waiting to get their picture with Santa. We never waited in that line when my kids were little. We always went to the real star of the day, the motorman. Santa may have a sleigh, but it’s the guy driving the L who is the true hero on CTA Christmas Train Day.
After the engineer come the elves. CTA employees dressed up, handing out buttons and candy canes, smiling like they mean it. These are the real celebrities. We found Mr. Carr, the motorman who has been in most of our photos over the years. He said the boys were giants now, asked where Hazel was, and noticed again that there wasn’t a grandfather with us this year. That is what you get when you build a relationship with a class act.
George chatted up a CTA elf while we waited. At the end of their conversation, the elf told me the CTA was hiring, and that my son ought to apply. “His knowledge of the lines and equipment is impressive,” he said. I told him George was neurodivergent. The elf didn’t blink: “We work with several George’s already.” That meant more than he knew.
I thanked him for planting that seed with my son. I would be honored if one day George worked with Mr. Carr and colleagues who took time on their day off to spread joy to the world.
When the train pulled out toward the Loop, the city was covered in a blanket of white. We stopped at the station near my Oldman’s old house. It felt like he stepped on board right then and there. Fritz asked why I was smiling with wet eyes. I told him, “Your Grampa Don just got on at Ridgeland.” Fritz shrugged: “You always say heaven’s closer than Oak Park.”
The train packed in, riders soaking in the lights and music, faces glowing like they were seeing magic for the first time. It reminded me of the first time the Oldman and I rode it back in the nineties on the old Congress line. Just me and my dad, much like this year. A father with his son creating lasting memories.
As we entered the Loop, the crowd thinned. By the time we left the last downtown stop, it was just a handful of CTA elves, a few Black people heading home to the Southside, a couple Orientals going to Chinatown, and the Shepley men. It was peaceful and warm creating a small pocket of quiet in a loud world.
The Christmas journey arrived at our turnaround station. George sprinted down the platform at 35th to thank Mr. Carr one last time. From his window at the front of the train he yelled “See you next year! Bring Hazel!” through the snow and wind. That moment slowed us just enough that we missed the northbound ride home. The doors shut and that warm train was gone. Now we were stranded on an exposed platform near Comiskey Park, De La Salle, and IIT with the wind slicing right through us. The next train was in twenty minutes.
I wasn’t thrilled, but George needed that last goodbye. So, we waited under the heat lamp. That was when an older man, beaten and tired by life asked if I could help him get food and water. I turned away so he couldn’t see my wallet, then slipped him a couple bucks. We exchanged a “God Bless” and he wandered off into the swirling snow.
I didn’t give him money to feel noble. I didn’t do it for an audience. I did it because my boys were watching. They saw the street smarts and the humanity, two things Chicago demands in equal measure.
I asked if they were cold. “Kind of, Dad.” I told them when the train comes, we will go home to Riverside, to heat and dinner. That man was staring down a storm that could kill him. One storm is an inconvenience for us and a possible death sentence for someone else. That was a lesson no classroom teaches.
Our train finally arrived and just like that, we went from holiday joy to brutal reality. Litter on the floor. Smell of urine. A crack pipe lit in the corner. Four young Black kids laughing at the junkies, because that’s their normal. Fritz pulled out his phone, suburban innocence on display. George looked at him and said, “Put it away. Head on a swivel.” That’s the autism I love—straightforward, observant, unfiltered and correct.
At Roosevelt, a street woman shoved her shopping cart onto the car.
This is Chicago.
Not a brochure.
Not a Hallmark card.
Not tourists sipping hot wine at Christkindlmarket.
This is the real city and I was glad... yes, glad that the boys saw both sides. You don't plan these lessons. Life hands them to you when you pay attention.
Back in the neighborhood, George asked if we could go to PopPop’s McDonald’s. It was where we used to go whenever he was with us. Last time he was there, his nose was running like a busted hydrant; I grabbed him a stack of napkins as we sat and ate Big Macs together. Yesterday, sitting there without him, my eyes filled again. I missed him. I missed the joy he received spending time with his grandchildren on the train.
We got home and the boys disappeared to their rooms, silent and spent. A day of magic, snow, family, and hard truth will wipe out even the toughest kid. The CTA Christmas Train delivered again.
I’ll keep taking this ride every year. Riders will come and go. I know George will probably always be my constant. Someday I may ride alone and someday the train will leave without me. I will be with Grampa Don and Pop, watching to see if the lessons we passed down are still being lived.
Okay Chalkheads... shovel smart, fill the crockpot with something that smells like love, and hold tight to the person who fits your jigsaw.
End December with gusto and astonishment.
PopPop with the Shepkids on one of his last CTA trips.
