I started doing long day trips in my early teens, then found AYH in New York City, and started doing weekends to destinations a bus or train ride away, ir/ Penn Dutch area, Catskills, the Berkshires, etc.
When I was 16, a high school friend and I signed up for a 4 week trip in New England, working it's way from Burlington Vt. to Cape Cod at about 40 miles a day. This was my first experience in long term group dynamics, and helped seal my fate as a bike tourist. Soon I was leading trips, and part of a small circle of experienced riders who'd go for "private" trips of 100 miles per day, or in some cases much longer.
Once a cycle tourist, always a cycle tourist, though if I could live the dream, I'd have a 36' sailboat, set up for full time living, with bikes aboard for land transport.
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WARNING, I'm from New York. Thin skinned people should maintain safe distance.