Some of you may be tempted to think that what you’re about to read is a bit of heartwarming fiction. It’s not. This happened to me this morning, and I feel compelled to share it with you on a day when we intentionally set aside time to be grateful for what we have. Not that Thanksgiving is the only day we should be doing this (I’m trying to make it a daily practice), but the fact that this happened today feels like one of those moments when God decides to get your attention.
My Thanksgiving tradition for the past seven years has been to start the holiday with the 5-mile Turkey Trot (8KM for my metric friends) up in Westport. The Pequot Runners put on one of the best races of the year throughout Southport and Westport, with views of Long Island Sound in the early and later parts of the run. I love this race and look forward to it every year.
But this morning when I woke up, I wasn’t feeling it. I also wanted to make the 9:00 AM Mass at St. Leo, and an 8:15 start up in Westport would make that impossible. So I decided to get the miles in closer to home (a hillier route, but I’m used to hills living in North Stamford). And that’s where this story begins.
I took a left onto Long Ridge Road heading toward Riverbank when what to my wandering eyes should appear about 200 meters ahead but a man zig-zagging up the road. As I got closer, I could see he was carrying five plastic shopping bags—three in one hand and two in the other.
As I passed him, he stopped me.
“Which way to the Stamford train station?”
He was walking north, toward the Westchester border—completely the wrong direction. For context, we were over three hours away from the Stamford station on foot. I told him he was headed the wrong way and tried my best to give directions.
“I was confused. I saw the sign for New Haven so I figured I should walk the other way,” he said.
He was referring to signs for the Merritt Parkway miles away. He told me he’d been walking since midnight. Something was clearly off—but there was also a gentleness to him. He didn’t seem threatening. Just lost. Maybe figuratively as much as literally.
He turned around and headed south. I kept running. I eventually finished the miles, cleaned up, and headed to Mass. It’s not lost on me that the song playing on my playlist was Rod Stewart’s version of Bob Dylan’s Forever Young. “Do unto others as you’d have done to you,” was sung in my ear once I started up again.
Here’s where I pause to tell you the part I’d rather not admit:
I’ve struggled with the holidays lately. I’ve been open about my grief over losing my mom and my brother. That grief gets louder during the holidays. I miss them both terribly. I think about my dad spending Thanksgiving alone in his assisted living facility (or “his prison,” as he jokingly calls it). I miss him too.
I haven’t been feeling grateful for much lately. I was overdue for a shot of grace.
And I got one.
Driving south on Long Ridge—who do I see again? The mystery man. Still walking. Still carrying those five bags.
I was tempted to keep driving. But I didn’t.
“Michael, that was stupid!” I can hear my father’s voice in my head even now. Maybe it was. But something in me knew it was the right thing and that I had nothing to fear.
“You still want to go to the train station?” I asked.
“Oh yes!”
His eyes lit up like a kid on Christmas morning who had his own visit from St. Nick.
As we drove, he told me he was heading to New Haven and wanted to get something to eat, but everything was closed. I reminded him it was Thanksgiving. He seemed genuinely surprised.
I heard a faint accent and asked where he was from. “Turks and Caicos,” he said. He hadn’t been in the States long. He told me he spent all his money on vacations and loves cruises—lots of food and casinos. He warned me, “Just don’t fall overboard.” I promised him I’d keep that in mind should I ever go on a cruise.
I dropped him at the New Haven-bound side of Stamford Station so he wouldn’t have to navigate the chaos. I offered him some money and he took it. He smiled—wide and toothless—and wished me a Happy Thanksgiving.
And I said the same back.
I sped to St. Leo and made it just in time. But during the drive, I couldn’t shake the feeling that on my way to God’s house, I may have met His Son first.
“Whatever you do to the least of my brothers, that you do unto me.” — Matthew 25: 31-40
So here I sit in my warm home on a cold day. A place where I’ve been struggling with gratitude.
Today reminded me that gratitude isn’t always something you feel. Sometimes it’s something you choose to do. And sometimes it’s something God does for you when you can’t find it yourself.
As I mentioned before, my father jokes that he’s living in a cell, and that image has weighed heavy on me. I’ve been walking around believing that he’s the one who’s trapped.
But the truth hit me today. I was the one in prison.
Not a physical one, but a prison of my own making:
a prison of self-pity
a prison of grief
a prison of ingratitude
And that man with the plastic shopping bags and a long road ahead was the key that unlocked the door to my cell.
We are all carrying our bags. We all walk in the wrong direction sometimes. And every now and then, God places someone in our path to turn us around—not just so we can help them, but so they can help us.
Today I am grateful—not because everything is perfect, not because grief is gone, not because I suddenly have it together—but because grace showed up when I needed it most.
And I hope it does for you too.
Happy Thanksviging
