Started touring when I was in college. First overnight trip during summer after my freshman year.
In high school in Colorado, I had done a fair amount of backpacking and camping. I had also cycled, though never overnight. Some with boy scouts and some with my parents - but I was camping at least once a month.
I went to college in Boston and took my bike with me and didn't have a car. Being in a big city was nice, but also missed being able to go into the great outdoors. My bike was my ticket to getting out of the city. I also had my tent and some camping gear as well.
So I organized a trip for my friends. Basic plan was to ride from Boston to tip of Cape Cod (~135 miles) and then take the ferry back.
The brakes on my bike didn't work well, but that wasn't a big deal since I could put my feet down to help slow me down
. Unfortunately, about 10 miles into the ride I went over the handlebars after missing a turn in local city park. Fortunately, I landed on flat of my back. Had a gouge in my back which we bought some bandages and taped me up.
After my crash, it would have been more prudent for me to turn back. However, I was young and invincible and toughed it out - a bit painful in afternoon when I sweated into the wound. We camped on the lawn of a church down on the Cape. Next, morning we finished riding to tip of Cape Cod and awaited the ferry for ride back. Felt triumphant cycling back through the city.
After that ride, I ended up doing a fair amount of further touring. Some were solo trips, some were organized trips with friends. Cape Cod was a common destination, but I saw quite a bit of rest of New England as well; particularly in summer after Sophomore/Junior years when I had a job working with DEC in Marlboro ~26 miles out of the city. I would commute to work on my bike (~50-60 miles round trip) but also sometimes sleep in my cubicle or camp out in the woods near work. Some weekends rather than returning back to Boston, I'd cycle further outbound the rest of the weekend. I did fix up my brakes and even bought a touring bike after my Sophomore year (Lotus Odyssey).