Wow that's a tough ride! How is the riding in New Zealand?

It was tougher the other way (though I was on day one of a two day tour, so held back on the climbs).
https://connect.garmin.com/activity/109644336

Riding is fantastic down here
on a good day.

I´ve entered several centuries/sportives by myself, but once you hack yourself into groups along the way it aint solo anymore. I´ve done 120 km solo a couple of times as preparation before centuries/sportives. I quite like it.

No solo centuries yet. I normally do at least a 45-53 mile ride on a Saturday or Sunday and get 15-30 mile daily rides in during the week. However, now that I am retired, this is going to change. Longest solo ride was 57 miles.

Was that a randonneuring/audax event?

When I was in Manitoba, I did the events (200K, 300K, 400K, 600K, and 1000K) mostly with others ... my longest solo stretch was about 300K in the middle of a 600K. I got dropped by a group of riders, and sort of hung about waiting for a couple I knew were behind me, but didn't want to wait too long so I kept moving and rode through the night by myself.

But in Alberta, there were fewer riders, and we were scattered all over the province, so I did most of the events solo (including, as I mentioned earlier, a 600K). At first it wasn't so bad, but after several years of that, it kind of dampened my enthusiasm for the really long events.

Definitely -- some people here would call that ride a "commute"

It's just a matter of what you like to do. I like riding solo, and at least half of my centuries are solo. I've never been bored on a bike or found myself feeling lonely.

Don't worry about having issues when you're out there by yourself. The solution is the same whether you have one or two people. The only difference is that you've just doubled your chances of the ride being affected by a problem.

Other than the increased efficiency of group riding, I don't think that there's anything inherently social when it comes to riding. I think that a tendency to ride with groups or ride solo says more about the nature of your personality than the nature of the activity. Personally, I relish the occasional time alone.

The only reason to do a group ride is to have some one to drop.

Except for the rare event ride all my riding is solo. Several centuries by myself and pretty much every weekend I get in solo 40 -60 mile rides. Am closing in on 7000 miles for the year with only one 100+ Grande Fondo event where I actually road with people.

I agree, I'm a social person. Since I'm off most of the year it means I'm alone most of the day while others are working normal jobs. I also enjoy talking (even though it may be hard and intermittent at times) bike talk. My other friends want nothing to do with my biking lifestyle, my girlfriend just tolerates it (although she enjoys riding just as much as I do, she's got better thing to talk about)

I really would like to try a century by myself...need to break the 50mi mark solo first.

Longest distance in a single day: 100 miles.

Longest distance solo: 1000 miles over 3 weeks from Sioux Falls, SD to St Louis, MO. I was also carrying everything that I needed to live.

Longest distance in the most remote location: 350 miles in a week in central Colorado...on a mountain bike...over the mountains...with a full touring load.

As for issues, you just deal.

that is......PRETTY BAD ASS

One thing that has always amazed me about Bike Forums is the number of people who do most or even all of their riding alone.
I've been riding road bikes since the early 80s and most of it has been with others. Sure, after work rides are alone but I am a member of a road club and there is always someone to ride with on weekends. If not the club I have other friends who ride, too.

To answer the op I have done solo rides around 50 miles, 4 hour climbing rides alone, and multi-hour off road rides exploring new areas.

22 miles is just getting warmed up! How do you know you are pushing harder because you are riding with someone else? What if the other person is the slower rider? Are you going to keep riding at the slower pace just to have someone to ride with? The best part about the longer rides is their Darwinistic nature. At some point you will have to press on by yourself. Someone tires and people either get dropped or do the dropping. Then you are out there with your buddies me, myself and I. You have to face the wind, rain, heat, hills, etc. by yourself. That's what it's all about. No talk of MPH, Powermeters, Watts, etc. Just you trying to persevere.

As a follow up, if you think "competing" with your buddy/buddies is fun over a 30 mile ride, try it on a Century. A Century is nothing more than a 1 day ride/race with stages. If you are evenly matched, everything is critical. Bathroom breaks, hills, etc. are all important. A 100 yard break early or a slow rest stop may be the difference. Are you the hare or the turtle? It's up to you. That's what makes it fun. It can be your 1 day version of the Tour De France!

I wish I had a Garmin 800 so I could go out further (longer distances) to places I haven't been

Why do you need a GPS for that? Look at a map, route your ride and go for it. Back in the day before electronics, somehow people got by. I'm assuming you can read road signs?

My longest solo is ~55 miles. but of my 3200 miles this year 99% is solo usually in increments of 20-35 miles.

I've never needed a GPS to know my position. I carry a compass and a length of 550 cord and I am set

So what is stopping you from those longer rides then? Trust me, they are fun and rewarding.

Pick a day with great weather and a route that looks enjoyable and go for it! You already do 30 miles, whats another 20?

Before getting my new bike, I hadn't been on one in years and had never been on a road bike. My first time out I did 20 miles. The next week I did 40 miles, then 60. Admittedly I started out in really good shape because I'm a runner, so no way I could have hopped on the bike and done 60 miles that soon otherwise. I still paid for it though as cycling works your muscles in a different way than running, but it was still a great ride! Some people prefer to stay around 40-50 miles solo because it can be difficult without having someone to draft at times when pedaling into a head wind, but otherwise I enjoy riding long distances solo. It's good, quiet, alone time. If you get out in the country, you feel as if its only you, the road, and nature. Really a peaceful and rewarding experience.

You don't even need that. You can just pick roads and see where they take you.

I've gotten seriously lost only once in my life using this method. I was so disoriented that I didn't even know which direction my home was. So I just asked some guy in a small town if he could point in the general direction of my town. He was pretty shocked when I was happy to hear I was only 40-45 miles away.

Question to the OP,

What is the longest ride you have been on period? If you are worried about a 50 miler by yourself, I wonder if you have been on any rides above 50 miles anyway.

I think an interesting topic for another thread is how one's cycling interests evolves or changes as he/she get's older and more experienced. Some of the best rides and experiences are the ones like banerjeks example above.

With one exception, it's usually the opposite for me, because we get more leisurely and talk instead of focusing on the ride. I do have one friend that bumps my pace up (even while chatting), just because he's so much faster than me, even when he's not pushing the pace.

Oh, and to answer the original question, a couple of solo centuries would be my longest solo rides. But 80% of my riding is solo, so I'm doing 60-ish mile solo rides just about every weekend.

Bear in mind, as the rides get longer an old school Fredly metamorphosis might take place. The full race CF bike might give way to something more suited with bigger tires. The matching team kits start getting replaced with more subtle clothing. Then next thing you know you are looking at rear racks and handlebar bags! Finally, you turn full circle when you decide to ditch the compact crank for a triple touring setup! Oh the horror!