My brother Jeff had just moved to Denver, and I decided to drive down there for his housewarming party. From out of the blue, Jeff had called me one night, and the next thing you know, Jennifer and I were packing for the trip. It was a rather nice housewarming, as Jeff showed us around his new place. We also took a tour of the Mile High City, and he was nice enough to take us to a Rockies game at Coors Field. But being from Chicago, Jeff will always remain true to his roots, rooting for the Cubs. He's a Rockies fan now, but not when they play the Cubs.
4--Yellowstone (1991)
This is when I took my relationship with Jennifer to the next level. I decided to take her to Yellowstone National Park, and she agreed. We camped under the stars and kissed under a full moon. And it was at the Old Faithful geyser that I proposed to her. I decided to save the ring for a special occasion like this, but she already knew of my intentions. Anyway, it was a very special moment, because how often does someone propose to his girlfriend at Yellowstone?
3--Chicago Christmas Trip (1998)
I had the whole Christmas week off, so I decided to surprise my parents by going home for the holidays. And this was Ashley's first-ever trip to the Windy City. She was four at the time. I showed Ashley around Chicago, and Jennifer and I went shopping at the Loop. I even managed to get my mother a very nice gift: a new Cadillac STS. When I gave her the keys, she was crying, and then told me that this was the greatest gift she has ever gotten. It was a perfect time for a new car, especially since the rusted Cutlass was still hiding in the garage (it shows up on Route 66). Merry Christmas, it definitely was.
2--Los Angeles to New York (1997)
I decided to make a trip from Los Angeles to New York and back. It was quite an adventure, as I encountered some bad traffic and construction zones at the absolute worst times. But I made it all the way to New York, and on the way back, I made a short visit with my parents in Chicago.
1--Route 66 (1975)
I remember my first road trip like a kid remembers his first day of school. As a little five-year old, I rode in the back seat of my father's '69 Cutlass convertible (yes, that really was my father's Oldsmobile!). It was red with a white top. Anyway, we went the entire length of Route 66 from Chicago to Los Angeles. I guess it was a lot easier to drive Route 66 back in 1975 than it is now, because at the time, the Interstate system was still undergoing major construction. It was a great trip, and I will never forget all the attractions we visited along the way.
In 1988, after my high school graduation, I decided to move to L.A. and attend UCLA (Go Bruins!). I met Jennifer in my freshman year, and we've been inseparable ever since. I owe it all to Route 66. Thanks for the memories!