Hi phieralph, I was looking around this forum for the 1st time tonight and your thread caught my eye. Not sure how useful my help might be, but I'll take a crack at it. I completed a similar cross-country ride many years ago at the age of 22/23. It was right after graduation from SUNY Stonybrook in 1981. That summer a friend and I decided to ride from Suffolk County, Long Island, to San Francisco. We both had a lot of riding experience by then, including countless 1 day rides out and back, a few overnighters, and racing/training experience on a local club racing team. We both knew how to fix everything and anything on a bike. I would echo the previous recommendation that you learn more about bicycle repair and maintenance than just fixing a flat tire, as you can likely expect various mechanical problems/breakdowns on a ride of this magnitude. On our cross-country ride, we had numerous flats, numerous broken rear spokes, derailleur issues, the need to adjust headsets, bottom brackets, and other problems I'm not recalling at the moment. Bear in mind, we did this on steel framed 10 speeds from over 30 years ago, and the bikes were loaded to the hilt with gear. 80 lbs each. Each bike had front and rear Blackstone racks, front and rear paniers, and handlebar bags. We carried everything with us on the bikes we would foreseably need, including clothing, a complete assortment of tools, spare tires, spokes, tubes, food, water, coleman camping stove, cooking utensils, eating utensils, flashlights, cameras and film, batteries, a 2 man tent, sleeping bags, maps (this was obviously before the days of the internet, smart phones, GPS, etc). In addition, I was actually relocating from Long Island to San Francisco as I was going to be starting medical school there, so I brought a few other little tidbits as well from home that I would need to get settled in. This all adds up!
We covered 4300 miles in 43 days of riding and a total trip duration of 2 months spanning June and July 1981, I had to be there in time to register and start the Fall Semester at the start of August. The days not spent riding were spent staying a few days here and there at various places of interest, including my relatives in the Catskills, Yellowstone, etc. We camped out the entire way, with the exception of various unexpected invitations by nice folks we met along the way once out of the bigger cities who generously offered us their hospitality and put us up for a night as they were so intrigued by what we were doing, and various places along the way where we could stay at youth hostels for next to nothing and for performing chores while there in exchange for a roof.
We really were very surprised with the friendliness and generosity of those folks/families and accepted several of their offers graciously. When camping, this was at times in actual campsites/camp grounds, but most often we set up camp in makeshift locations along the way ( wooded areas off the road, town parks, behind churches, etc). This may be less of an option in this day and age.
Another somewhat unexpected thing was how many cyclists we came across who were also in the midst of a cross-country trip, though the vast majority of them were conducting their journey in the easier direction from the west coast to the east coast. That's right, you are planning your trip in the much more difficult direction of east to west. The head winds were ever present, often extremely persistent and difficult to overcome. There was one day crossing southern Canada, just on the north side of Lake Erie, that the head wind was so brutal, we barely covered 10 miles all day. We had one day of 180 miles, in which we rode all through the night practically to make a certain destination deadline. On average, we covered 100 miles per day. Aside from the fact that 100 miles a day, day after day, on heavily loaded old school steel bikes against frequent headwinds was physically taxing, at times, one would be so tired and contemplating the vast number of miles traveled and the many many miles still ahead of us, that it was as much a mental strain as it was a physical one. At times, the mental strain was more taxing than the physical demands, so you have to tell yourself this is probably the only time you will complete such an accomplishment and mentally will yourself to push forward in spite of the exhaustion, burn out, periods of isolation, bleeding saddle sores, blah blah. There were times it would have been easy to toss the bikes on a plane and head home, rather than push onwards, but to have done so would have been a huge defeat and personal letdown. Now I'm not saying every day was like this but there were many times when such mental struggles were encountered.
Our trip took us from eastern Long Island, across New York state, to Buffalo, into Canada at Niagra Falls, back into the US at Port Huron, Michigan, across the state of Michigan to Luddington where we ferried it across the lake to Manitowac, WI (had to make up for unexpected delays or else risk not getting to San Fran in time, the only part of the trip I regretted but I had to do it), across WI, across northern Iowa (we apparently made quite an impression on the good people of Riceville, IO, as the local newspaper got wind of the 2 New Yorkers in town pedal-cycling their way across the country that their reporter met up with us in the town park where we were resting a bit after having lunch of PB&J sandwiches and Fig Newtons, and proceeded to interview us - we would later make it onto their front page lol), continuing into South Dakota, crossing into WY where we spent several days in Yellowstone (I'll never forget being chased on foot in Yellowstone by a ******-off moose who thought I got just a little too close to her calf to get a picture), across the arrid southern part of Idaho, into Oregon, northern California (the "Welcome to California" road sign was another unforgettable moment even all these years later) to the Pacific coast at Crescent City, down Hwy 101 to Hwy 1 (where I survived getting hit by a lunatic Georgia Pacific logging truck driver who had a thing against bikies - good thing my Bell Helmet was up to the task) and across the Golden Gate to SF. 2 months and 4300 miles later, destination reached! Even after all these years, in many ways I still consider this my greatest and most difficult achievement. It provided me many memorable experiences and I am glad, and proud, to have accomplished this. If you do a trip like this, it is something you will look back upon and recall with vivid memories the rest of your life. It will be something that in many ways, will set you apart from the herd. But you need to be prepared mentally and physically, be suitably equipped and also knowledgeable about maintaining and fixing your bike along the way, and also financially prepared for the expenses you will encounter along the way. Also, doing a road trip like this solo is probably more difficult than having a riding buddy with you. There were many times that having a friend right there was a tremendous asset, and the mutual support you provide each other cannot be overstated. If you can find a suitable and experienced friend to ride with you, I would strongly encourage this. Best of Luck if you undertake your cross-country journey - stay safe!
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