By the time I moved to Wyoming it was my 5th time driving cross country. Let me define what I mean by “cross country” vs “across the country”. Cross country to me is when you drive across at least 3 time zones. Because, c’mon…the US is a big country, you drove far enough to cover most of the country, give yourself some credit. Driving across the country is literally when you drive sea to shining sea. That is a feat in its own. But three time zones is plenty, trust me. One way to me means you drove cross country. Roundtrip means you drove cross country twice. Think about it.
When I lived in the northeast a friend and I had started taking an annual road trip to Kentucky every April to attend the races in Lexington at Keeneland Racecourse. On our first trip there, on a hankering to get out of town one weekend, we were met with some of the warmest, friendliest, most welcoming people and we were hooked on being around more of that. As we stood at the rails on a far turn at the Keeneland Racetrack on that first trip we met a man who started talking to us then invited us to visit his stables. We said thank you but we had to pass as we had to get on the road the next day. As it turns out, that was one of the dumbest things we have ever done was to pass up an invitation to tour a horse farm there, as they don’t let many strangers thru their gates. As we drove around the back roads to see the horse farms someone flagged us down after seeing our out of state license plates and said, “I just wanted to say welcome to Kentucky.” From the northeast it was about a 12 hour trip. We drove down on a Friday, went out and had some fun at our favorite watering hole, drank too much bourbon, got up Saturday and drove around the beautiful scenic byways thru the picturesque horse farms and then went to the races in the afternoon, then dinner at one of our two favorite restaurants, followed by more bourbon, followed by the longest drive ever on Sunday morning. It was kind of nuts. Each year brought a different adventure, from waiting out a tornado warning before we could leave, to hydroplaning all the way home in terrible rain storms, to me going on crutches one time after knee surgery.
One year a friend from Japan decided to join us and we decided to extend the road trip as far as Colorado. Your first view of the snowcapped Rockies is really the only reason to ever blast John Denver on your stereo, so that is what we did. We stopped in Boulder for a couple of days, stopped to have a look at Red Rocks Amphitheater in Denver, and on to Vail where it snowed while we were still in our shorts. It was epic. It was really my first long road trip. We listened to Dave Matthews’ album recorded live at Red Rocks to fit our Colorado theme, where he thanks his back up singers often calling them “the lovely ladies”. We named our rental car after the horse who won the big race we went to in Lexington, named High Yield. We called ourselves “High Yield and the Lovely Ladies” and as we bought beer at every big stop it became known as the longest beer run ever.
That trip checked off a few new states for me. It was when I drove out to Wyoming and camped for 16 days along the way that I really checked off some more. I had been home at my parents for a long weekend a few weeks before when I decided to buy a car. I hadn’t had one in many years. That meant having to park it somewhere. I knew my time was limited so I did the park-on-the-street thing. Some days I moved it 3x in a 24 hour period for street cleaning. I told very few people I had bought a car because I knew they would suspect I was leaving if I had a car in the city all of the sudden. On this particular trip I left from central New York after picking up camping equipment from my sister. I stopped to see Niagara Falls then crossed into Ontario enroute to see a friend who lived in Ann Arbor, Michigan. This was before GPS and solo it was really hard to read a map as you drove so I got really really lost in Canada. I got in to Ann Arbor very late and missed out on time to catch up with my friend. I continued on and drove like crazy to get to Wyoming where I stayed for a few days making sure my decision was the right one.
On the way back, as I mentioned, I stopped at a friend’s wedding in South Dakota and afterwards I headed to North Dakota thinking when would I ever be there again? (right!) I arrived late at night in the tiny town of Medora outside of Teddy Roosevelt National Park. It was a place I hadn’t thought much about and it was a pleasant surprise to wake up and explore this cool corner of the country. From there I headed across Minnesota, camping at one of the 10,000 lakes this state boasts about on their license plates. When I checked out of the camp site I wrote on my paperwork, “1 down, 9,999 to go”. After that I headed south of the Great Lakes and back to NYC.
When I finally moved out of NYC two weeks later I left early in the morning and again, drove to my sister’s house in Central New York where I attended a friend’s wedding. I had literally moved out of my apartment that morning in the dark! I was so tired I took a nap in my car between the ceremony and reception. I then went to my parents in Northern New York for a few days and reloaded what I was taking with me and started my 5th cross country trek this time in another country, Canada, driving across Ontario. I crossed back into the US in Sault Saint Marie, Ontario and Michigan (same town name, different countries!). I was now driving across the Upper Peninsula of Michigan! (Check!)
From there I avoided interstates and drove the entire way cross country on two lane roads, mostly out of cell service, only looking at maps to find my way each day. It was a soulful and quiet adventure I had all to myself. I stopped by Lake Superior along the way in Michigan, and was taken with Duluth, Minnesota when I passed thru, and then surprisingly I went across North Dakota again! I hadn’t planned it that way, but it put me in a position to drop down into Wyoming from the north, thru the rugged mountains of Montana and over the storied switchbacks of Bear Tooth Pass. I stopped at the top where the state line is and remember looking into Wyoming thinking, “I’m home.”
What did I arrive to, you might ask? Nothing. I knew no one, I had no where to stay, I only had a part time job lined up that wasn’t starting right away, and I only had what fit in my Jeep. I checked myself into the hostel in the ski village for a few days while I looked until finally finding a room to rent with a crazy local woman for a few months while I figured things out. She had a cat named Maggie I talked to more than any human in the first few weeks. What I had set up for work, though, had come to me from my job in New York. As part of my job at one point I had written a proposal and budget for a client entertainment trip for my boss’ biggest client, the CEO of a major international company. I knew who he was, had heard him speak at a conference, knew his two assistants, and knew he owned a home in Jackson Hole, but I didn’t know him personally. In a totally bold move sometime over the summer I called his assistant and asked if they needed any help at their house in Wyoming. To my surprise his wife called me and said yes, they did! So when I did give my notice at work I already knew that I was going to work for my boss’ biggest client in some capacity, someone he bent over backwards to get in to see and to entertain to get his business. Needless to say when I left my boss threw me the biggest going away party. Ask anybody at an investment firm….when someone leaves, there are no parties. Ask anyone who went to this one… it was huge. I would go on to work for them for 7 ½ years. They were the most down to earth, outdoorsy, nicest people who taught me a lot about giving and volunteering, getting outside and seeing the world. Oftentimes when I picked them up at the airport they were on their way in from some far away place in the world for business. And there were many times I dropped them off at the airport that we were meeting a family they were doing an Angel Flight for, where they transported a family to a children’s hospital in their private plane to get them special medical care. Over the years I planned events in their house that ranged from their anniversary weekend with their closest friends to a private dinner with the Vice President of the United States and the Secretary of the Interior (yes, at the same dinner!). They put faith in hiring me on this crazy move I was making and I hope I delivered what I said I would. Their house was on a ranch in a special place in the National Park, with a picture window lined up to view Grand Teton with a telescope on it to see the climbers, which they hiked almost every summer as well. It was snowmobile access only in winter, and risky to get into in spring due to mud and snow, I had to be pulled out once or twice over the years. Wild animals wandered thru- bears, bison, moose, and a snowshoe hare who became my favorite every spring when I went to open the house while the snow lingered. The days I spent at their house were always good days. The views, the fresh air, the wild, isolated feeling of it was what I was there for. I spent that first year in Wyoming never leaving the valley. My travels had come to a halt as I worked at establishing myself there and I loved it. I found a job at a resort and began to build on a long event planning career under an incredible woman who would become my mentor. I also built up a portfolio of beautiful homes I managed for homeowners, some of whom I would work for for many years and would feel a little like family when they came to town. I was making sure this move was exactly what I had wanted it to be when I left the city.
Even with slow, rocky beginnings I was still living in paradise and I knew the world would still be there when it was time to start exploring again.
Now 5 cross country trips under my belt taking 5 different routes I had 36 states down, and 14 to go. Reaching 50 seemed doable, right? That’s right!