Trail Moments, A Winter Story Challenge
Looking back, looking ahead by sharing the stories our trails gave us
With Christmas over and the calendar turning, days remain short and dark. For us in northern winters, trail visits are more often memories than actual rides or hikes.
January is a quiet time for biking and exploring trails. With snow and cold, I look forward to warmer days, new gear, and returning to my favorite trails. For cyclists, walkers, runners, and skaters, January is a time for reflection and anticipation. These are memories that matter.
Tom on the Trails just reached 500 subscribers! I appreciate your support as I share my views on trails, cycling, and advocacy for the outdoors. To celebrate, I’m launching a January community challenge, Trail Moments.
The Winter Story Challenge
This January, I’m inviting you to recall a trail moment that lingers, whether it happened on a bike, on foot, in running shoes, skates, or any way you move outdoors. By sharing, we celebrate the trail together and learn from one another’s journeys.
Each Friday, I’ll post a prompt for the week’s theme. I urge you to respond with a short reflection (under 500 characters) within a few days. I’ll share my thoughts on the prompt and highlight those from the community.
Week 1: The Unexpected: “Well… I didn’t see that coming” trail moment
Week 2: Chance Encounters: The stranger you didn’t expect to meet and never forgot
Week 3: The Spark: The moment you almost turned back and didn’t
Week 4: A New View: When the trail changed how you saw yourself and others
Week 5: Something Bigger: That moment you realized the trail was more than just a place.
We All Have Stories
Tom on the Trails often focuses on cycling, but this challenge welcomes any trail experience; whether you’re walking your dog, hiking, running, skating, commuting, or just finding some peace. I want to hear these stories.
When we share these Trail Moments, we’re doing more than swapping stories. We’re helping others picture themselves out there, maybe for the first time, or finding their way back. We’re lifting the places that connect our communities and remind us why the outdoors matters. Each week brings a different kind of memory, building a shared picture of the gifts trails offer.
I hope you’ll take part by writing, reading, reflecting, and encouraging others to do the same. Let’s turn January into something more than waiting for the spring thaw. Let’s use it to remember why we ride, walk, run, and return.
The First Prompt
The Unexpected Turn: That “Well… I didn’t see that coming” moment on the trail.
Submissions for this first prompt are open through Friday, January 2. Over the following weekend, I’ll gather highlights and share what this community has to say.
Thanks for being part of Tom on the Trails. Let’s keep celebrating the stories that carry us forward until the trails thaw, the wheels turn again, and we’re back out there together.



