The first one I'd describe as overnight tour was ~135 miles from Boston to tip of Cape Cod. It was memorable, though mostly because I had faulty brakes and went over the handlebars ~10 miles from the start and was headstrong enough to continue the rest of the trip despite a painful nasty gash on my back. It is the sort of adventure that is sometimes better looking back on than living in the moment. From there it had been a progression of trips with increased length and time.

Though hardly a first tour, my first transcontinental trip nine years later also held a special memorable place and influenced my outlook on life and approach to cycle touring. It was a more aggressive trip than I would do now (3475 miles from Astoria, Oregon to Boston in five weeks). However, it got myself completely in the flow of living as a cycle tourist and focus during the trip. It was a time of transition in my life with multiple high-stress events happening that year and spending some long hours on the bike gave me a chance to reflect and work things through and develop a better understanding of who I was and what was important to me.

That first trans-continental trip influenced me in living a bit more simply and also in working towards a longer extended multi-month cycle trip which I've been fortunate to do every 4-5 years after that.