I did my first overnight ride in 1999, the weekend that JFK Jr. died. My excuse was to get my best friend, a guy who had always had physical limitations and was recovering from hip surgery at 37, out of his depression.
He had a K-Mart Huffy. I had my 3-year-old GT Outpost, which I still ride today. Only back then, it had all its stock components and accessories. We rode thirty miles from our hometown on Long Island to a place called Port Jefferson, which has a ferry that crosses Long Island Sound to Connecticut. Then we rode about another eleven miles to an old HOJO hotel my wife and I had discovered many years earlier in Milford, CT.
The ride took forever, as I was constantly waiting for him to chug his way up even the slightest hills. He also had to stop at a convenience store for water every ten minutes or so, because he didn't have a water bottle. Both of us were riding with backpacks and in cut-off denim shorts, so we were roasting all the way in the 90 degree + heat. When we finally arrived, we felt like we had conquered the Southern Tier or something. Then we drank too much and rode back to the ferry the next day totally hung over. (Ended up taking the train home from Port Jeff!) This was a great accomplishment for him that he has never stopped talking about, so I am glad I did it. For me, personally, it was the beginning of my love for (what I call) bike touring.
I rode the same route about a month later by myself and it took me about 1/3 the time. THAT inspired me to do my first multi-day trip the following year. This trip involved a ride out to the Pt. Jeff ferry again, then a ride up the coast of Connecticut all the way to Narragansett, Rhode Island. I have never calculated the mileage because I used so many off-the-beaten path routes, park cut-throughs, etc to really figure it out. I do remember that most of the few days were about 50 miles, while one day was more than 70. My average speed was about 10-11 mph, including stops for photo opps and payphone calls home. It was on this trip (in Old Lyme, CT, to be exact) that the chafing of my thighs finally got to be too painful and I finally traded in my cut-offs for a $50 pair of bike shorts. Of course, I have never turned back (although some of you have pointed out that I have been wearing them incorrectly all this time!).
My father's health began to deteriorate significantly after that tour, and in the summer of 2001, I only took a shorter ride. He died that year, and then came the 9-11 terror attacks in NYC. From that point forward, life was a bit more hectic, with job changes, etc. Plus, it took a while for me to want to get on a ferry or be away from my wife (in the event of an emergency) again. By 2002, I was working at a job that had me on a plane virtually five days a week and totally exhausted by the weekend, so while I continued doing short overnights, I had no time or energy for another multi-day.
Now that I am semi-retired and working locally, I'd like to find time for another multi-day ride. The overnights are great, but not long enough to really let go of all the stress and just be with the bike. I have now completed the entire shores of Long Island and Connecticut in pieces, but I think I might like to cover the whole distance in one trip one of these days.