I have never done so - One of my week-long touring companions had no kids and did an E-W Transamerica and had a blast - I'm in awe of everyone who does so! Same for Appalachian Trail through-hikers. 

At all my different life phases the desire to do so never overcame the desire not to:

1. Fresh out of college, low job pressure, single, no kids, but no money in the bank -  at age 12 two friends and I threw sleeping bags on our bikes and biked 100 miles out to Montauk on Long Island NY. I graduated college in 1978, and some college friends had heard of the Bikecentennial ride in 1976 and were planning on doing it after we graduated -what is now known as a "gap."
   
   I had big college loans to pay off and was the first in my family to graduate college - the concept of a "gap" wasn't really in my vocabulary!
2. Early work years - by 1980 I was working at a very interesting job, with lots of travel, I wasn't interested in a gap. By 1994, I was but...
3. Kids - my daughter was 4 when I made a major career change and family biking was a big part of our weekends.  Weeklong touring with 3 friends (and once doing the C&O Canal Towpath with my wife) filled the space without being away for too long at a time.
4. Empty Nest - over the years, I had become the organizer of what became to be called Camp John and every summer getting big groups of friends to spend the weekend biking on the Great Allegheny Passage Trail, rafting on nearby rivers and hiking on nearby trails. I had always enjoyed the logistics of planning trips almost as much as the trips - creating ways for 20 people to mix and match outdoor activities while I did a lot of biking scratched that itch.
5. Grandkids - goto (3)

When I was younger,
So much younger than today...

In my youth I wanted to, or believed I did.

Last summer I started to, although my journey neither began on nor would have ended at a coast.

After 35 days, I called "Enough" and stopped.  I'm not sorry to have made the choice I did, and it's helped me realize and understand that I have personal and temperamental limits on how long I want to go about sustaining the life of a bicycle hobo.  It's fun for a while then (for me) it's ... just not.

It's fair to say that your tour last summer had an exceptional number of problems. You had more flats in the first two weeks than I have had in all my tours combined. In spite of it all you seemed to be pretty cheerful when I met you on the side of the road in Oregon (or was it Idaho?).  Still, I am not surprised you threw in the towel. I doubt I would have lasted as long as you did.

I rode solo from Mt Vernon VA to Portland OR in 2018. I was 62 at the time. I had been building up to it for three years. I cobbled my route together using four Adventure Cycling routes (NY to Chicago, Northern Tier, Lewis and Clark, and Pacific Coast). It was a solo endeavor and I was, as the Blues Brothers said, on a mission from God. Totally focused. 

The tour was truly life changing. When I finished I had what I called Afterglow. A friend of mine blogged about her experience with Ayahuasca and it sounded like Afterglow to me. 

I've also ridden 2/3rds of the TransAm and the entire Western Express. The TransAm is special because the people along the way are incredibly kind and generous. They've been dealing with bike tourists for nearly 50 years. The terrain, however, is much harder than on my 2018 cross country route. None of my climbs in 2018 were much over 6,000 feet. The climbs on the TransAm are routinely over 9,000 feet. Sadly, many of the towns on the TransAm are all but ghost towns. 

The Western Express is just plain brutal. No services. No shade. Lots of rocks. 

Of increasing concern is intense weather. Flooding, torrential rains for days on end, excessive heat, smoke from forest fires. Lions and tigers and bears, oh my.

Hi Kelly,

I had plans about ten or more years ago to do a US coast-to-coast, however for a few different reasons, mostly work and time, I wasn't able to swing it. 

In the interim, the desire to do so has waned. I think the reason for this is that as you do more touring, the mystery or maybe  the consideration of it as a challenge lessens. I know that, given 3 months, I could easily do it. The issue is more whether I could take 3 months away from my commitments at work and at home. 

So these days, an annual or twice annual tour of a few weeks is sufficient for me. Maybe one day if I am financially independent, and have fewer home commitments, then it would be on the agenda again.

Also, since I no longer live in the US, it is a considerable hassle to consider doing it. Being outside the US, I ask questions like - should I do Italy this year, or Czechia, or maybe that LEJOG needs to get checked off the list...

Cheers,

Emmet

Ten years ago, I set out on my bike from my son's driveway in Seattle to my driveway in the Minneapolis-St.Paul area.  At the time, that trip was all I ever intended my bike touring career to be.  Damn it all, at some point during the ride, I realized I was having so much fun that I wanted more.  The next summer I continued from my house to Boston, MA.

I kind of regret not doing it all in one continuous tour, but I guess I don't regret it enough to give it another try.  I still love touring, of course, but I've been content with making my own shorter routes in smaller sections of the U.S.--especially in the middle part of the country.  Maybe someday, when I've ridden every wonderful road in North America, I will venture off to other continents.  That probably won't happen until I'm, like, 120 years old though. 

I have, Oregon to Iowa in 1998 until the 100 degree plus temperatures stopped me and then finished it in 2001. Why?  I think because that is what you were supposed to do if you were a true cyclist. Would I do it again … maybe but the “rules” would definitely be different as the days of carrying all the gear and camping seem to be a thing of the past. Not sure I would really enjoy dong 70-80 miles days anymore either. I guess if I could rearrange my touring for the last 25 years I might have saved that trip for later as we now enjoy finding the trails, slowing down and it seems 3-4 weeks is long enough to be on the road for one journey. 

I'm known for long replies, so I'll try to keep this on track and to the point.  Not promising, but I'll try.  I've ridden the 2 longest ACA coast-to-coast routes, the  Transam and the Northern Tier, each about 4,300 miles.  I made a comparison of the 2 routes here (scroll down about halfway) --> Transam vs Northern Tier.   The Northern Tier was fine, but I don't plan on riding it again.  I hope to someday repeat the Transam, so I think that speaks volumes.   Here's some detailed discussion of the Transam route; Transam Planning Considerations, and here's the same for the Northern Tier route; Northern Tier Planning Considerations.

There are other coast-to-coast options, but those 2 should be towards the top of any "potential" list.   The Southern Tier is shorter, but you have to ride through the southern underbelly of the country - sorry to be so blunt about it, and others may certainly disagree with that sentiment, but after last year's Great Rivers South experience I feel strongly about it.  Because I've ridden the other 2 ACA coast-to-coast routes, I may someday ride the Southern Tier - but I have low expectations of it.  And you could ride a route consisting of the Chicago to New York, Eastern Express Connector, and the western half of the Transam.  But why?  Why ride just half of the Transam when you could experience it all?  Or similarly, you could ride the Chicago to New York, Eastern Express Connector, and hook up to the Lewis and Clark route. 

Like Jeff Lee, the Transam was my first long tour, and I was very inexperienced.  I was 62 when I rode it, and I fell in love with cycle touring from that experience - to say it was life-changing is an understatement.  The Transam is THE granddaddy cycle touring coast-to-coast route.  People come from all corners of the world to ride the Transam, and you will meet many foreigners - I really enjoyed interacting with some of them.    You will leap-frog with cyclists you met days before and it's very encouraging to have others doing the same route.  I met a few others on the Northern Tier as well, but it's a whole different game on the Transam.  

Others have downplayed the significance of riding coast-to-coast.  I'm going to take a different view; it's a BIG FREAKING DEAL to bicycle from one ocean to the other.   I've seen big strapping men cry when they reach the end - not saying that I did, but it's an emotional high that lasts for weeks afterwards.  Riding coast-to-coast puts you squarely in the "epic" journey club; any journey greater than 4,000 miles must surely qualify as "epic."  And riding the Transam puts you in an even more elite club, because some of it is hard (yes, that was meant as humor).   If you should decide to do the Transam, you will meet a lot of very helpful and kind folks all the way across the country, and you will sign a lot of guest registers at hostels and restaurants and even stores - Transam riders get a little bit of Rock Star treatment.  Parts of it are hard, but there's no rush and you will meet lots of fellow cyclists to encourage you.  

Should you decide to ride the Northern Tier route, you will enjoy it too.  I'd recommend starting as early in the year as you are comfortable with because you are traveling through lots of touristy country until you reach Ohio (assuming an east-to-west route), and you want to get a jump on the tourist traffic.  It's a great route too, but it's not the Transam - there's only one Transam. 

And should you decide to design your own route, any route you do will be an epic adventure and I'll be following along.  Considering the topic, I kept this reply about as short as I could.  Best of luck,

Hi Kelly - 

I may not be the best person to respond to your question.
I've ridden x-USA a half dozen times and a whole bunch of halfways.
(Which really don't count for nuttin')

And - - ideally - - from sunset on the Pacific to sunrise on the Atlantic.
I mean, really, why ride 4300 miles and stop at Yorktown??
It usually takes extra effort to go all the way to the surf line, but hey.

One advantage of a cross-country ride is that you see different regions.
Especially those regions that are not on the Top Ten Cycling lists.
There are no E-W ACA routes across Nebraska, but it has fabulous riding.
Not to mention generous and welcoming folks in shrinking small towns.

Don't get me wrong, 
I love Going to the Sun Road and the southern Utah parks,
but it is the in-between that so often makes a tour magical.

Different folks like different styles - I prefer off the beaten path.
The Trans-Am will have you meeting other cyclists most days.
If you ever are interested, you can always ply me for info.

John

John,

I'm not sure if it seems stalker-ish to admit that I took your ideal cross country route and started following it as a motel only route back in 2019. 

This is how far I got before I started getting cross eyed. Cross Country was on Oren's bucket list. You always have good routing, and you had a more direct route. We ended up with the border to border trip instead in 2020 - which Oren didn't go on because of COVID. 

For the sake of discussion, and because someone else might truly be interested - would you change anything on that 3,200 mile route? Do you have a map?