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Ghosts, Gales & Goodbyes: A Halloween Sail Down the Chicago River
- erica trejo
- Oct 31
- 3 min read
There’s something poetic about the way sailing season in Chicago ends just as Halloween arrives. The warm sunsets of July give way to crisp October wind, docks empty out one by one, and the harbor slowly transforms from a summer playground into a quiet stretch of water waiting for the big freeze. And for many of us who grew up on the lake, the end of the season wasn’t just a task on the calendar — it was a ritual.
For my family, that ritual always fell just before Halloween. While other kids counted candy buckets, we were counting dock lines, prepping the sails, and swapping life jackets for fleece. And every year, like clockwork, we would make one final voyage: a slow, chilly, and surprisingly magical delivery trip down the Chicago River to tuck the family sailboat into her winter berth.
I remember stepping aboard in my costume more than once — a pirate hat over my knit cap. The bridges would rise as we approached, steel skeletons creaking overhead, and the echo of our wake would bounce off stone walls and skyscrapers like something out of a ghost story.
The river always felt different in late October — quieter, darker, almost theatrical. City lights shimmered off the water like pumpkins glowing on a porch, and I always imagined the river was telling us a final goodbye before winter pulled the curtain closed.
That delivery trip became even more meaningful after 2016, the year my father passed away on October 2nd. He was the captain of those fall voyages — the one who knew every current, every bridge tender, every trick for keeping fingers warm on a tiller in late October. The river run became a kind of living tribute after he was gone: a way to honor him not with flowers or speeches, but with the sound of a bow breaking water and the skyline unfolding ahead just the way he loved it. Now, each year as the season ends, I feel him most clearly in the small moments — a gust he would have commented on, a joke he would have made, the steady comfort of routine he taught us as kids. That final sail has become a remembrance, a ritual stitched with gratitude and grief, and one I now carry forward for him.
The adults sipped something warm from thermoses. And every time we passed under another bridge, I felt like we were sailing through a doorway — from one season into the next.
Now, as I watch our boats, instructors and students wrap up their own final sails of the year, I feel that familiar tug: the mixture of pride in how far they’ve come, sadness at packing the season away, and excitement knowing that rest is just part of the rhythm of the water. Boats need their winters, just like sailors do.
Halloween is a reminder that endings don’t have to be spooky — they can be sweet, reflective, and even playful. The end of the sailing season isn’t a farewell, just a pause. The sails will fly again. The water will warm. And one day, another young sailor will stand on a bow in a costume, feeling that same mix of river wind and wonder.
Until then — enjoy the candy, honor the memories, and may the ghosts of summers past keep your sea stories well-haunted. ⛵🎃
This post isn’t just about sailing — it’s about endings, memory, and the way traditions become anchors in our lives. It’s about how water teaches us to move forward while still holding on to the people and moments that shaped us. And it’s a reminder that every season, even the closing ones, holds its own kind of magic.
If you’ve ever marked time by the rhythm of a shoreline, a sport, a family ritual, or a loved one’s legacy, I hope it resonates.
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