On October 5, 2025, five of us met before dawn at the corner of John Muir Drive and Sklyine Boulevard. Our goal: Complete the new 38-mile Roundabout Trail . To walk the route in one day, we’d have to keep our bodies moving for over half a day with minimal stops, witnessing the sunrise, the full day, and the sunset. I’d walked up to 34 miles in a day on the NYC Shorewalkers Great Saunter , but 38-miles was terra incognita for me. Internalizing my learnings from the Great Saunter, I popped some “vitamin I” — or ibuprofen before we even started walking. Stats: Distance: 41.67 miles — 3 miles longer than predicted. Every extra step hurt. Steps: 81k steps — and I felt every single step beyond 60k. Time: 14 hours on the dot (6:30 am - 8:30 pm including all stops). Company: Started with 5, picked up 4 en route, and ended with 4 The Roundabout Trail is broken into five sections, and we decided to start somewhere in the middle of section 4 w...
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