The longest ride I ever took was 27 miles. I hadn't been on a motorcycle in 30 years and didn't listen to good advice and bought a new HD Heritage that I had to ride from the dealer in Salt Lake up to Park City, UT using backroads and then the last 8 miles on the freeway. I was scared shitless.
2004 HD Softail Heritage Classic
2008 Buell Ulysses
2008 Triumph Scrambler
Once in awhile you can get shown the light in the strangest of places if you look at it right. ADVrider Relay 2008: UT