Here's an game idea (not sure if it's new...)
 

It's basically a game that I've been subconsciously playing for the past 25 years. I've always loved highlighting my cycling routes on a paper map, and looking for new roads to explore on the bike. I have a map of every place I've lived showing a record of all the roads I've ridden there. A couple of years ago I thought it would be cool to try connecting all the places I've ridden into one giant web. So I came up with some rules and made this "game," and now offer it for your consideration and/or scrutiny...


Rules:

1. Buy a map or road atlas, or use mapping software that can display your full history of previous rides. This is the gameboard.

2. Trace, highlight or otherwise record any routes that you know you've already ridden. This is your starting point. There may be many disconnected routes grandfathered in that are floating independently from each other.

3. Every new ride must start at a location where you've already been on your bike, or intersect with an old route somewhere during the ride. When starting on a new land mass such as an island, then it is acceptable to start anywhere as long as subsequent rides connect with the original route.

4. Roads need only be ridden one direction to qualify. Pavement, gravel, trails, etc are all valid as long as they fulfill Rule 3.

5. Shuttling up hills to ride back down and make connections is prohibited. You are your only competition, so don't cheat yourself.


Has anyone else been doing anything like this? Is there something similar that has already been formalized in the realm of rando/endurance/adventure riding? Let's hear your thoughts.

Closest thing I've seen is trying to tabulate how many Texas counties I've ridden in. It's a bunch, but to try to go back through 10-12 years or riding and figure out just exactly which ones is a major chore.
On your idea, I'd need a wall-size map to do it, not aware of any way to work that on the computer.
One other map idea I've had, just start highlighting all the roads green, yellow, or red based on how attractive they are for cycling, then eventually you can create new routes just by stringing the green roads together.

The games I've heard friends playing include:
1. Picking an area (town, county, etc) and riding every road in it.
2. The VeloViewer squares thing -- riding in every square on a gridded map (I'm not exactly sure how big the squares are):
https://blog.veloviewer.com/veloview...nd-max-square/
is a good intro, and Eric Nichols, quoted on there as the best non-European at it at the time, is a randonneur in our area -- he's actually taken little detours away from (and back to the route right where he left, as required) during brevets to snag a few new squares.

If y'all use strava, you might find this site: Strava Multiple Ride Mapper Make sure you just select "ride" under activity types or it will put any virtual rides on the map, along with any other walks or activities you do.

It's like a heatmap of sorts that puts all your rides onto a map and you can see where you haven't ridden yet. You can just select a certain time period too, and download a klm file to do other things with it... pretty sweet little site.

I wish there were roads closer to me that I have never ridden on. Most of the ones in this area that I haven't ridden on entail at least a 50 mile ride. And there aren't a lot of those either. There are some dirt roads nearby I haven't ridden on, I think.

I'm in the same boat, most of the good roads an hour's ride around town have already been covered, and most of southern Ontario is laid out on a massive grid so there's a lot of roads and a lot of boring roads that I avoid, along with all the busier roads. I still like to try and get any roads that aren't on my heatmap, looking at it again there are a few I should go and get while traffic is still light, they are starting to reopen a few things here so more and more people are gonna be back driving around.

The idea of touching as many squares on a grid as possible works well with a road atlas. I can easily flip through and see which pages my rides have spilled onto. I like it, but so far haven’t made that a personal priority though.

Here’s another one: Try to “capture territory” by completely encircling areas on the map and connecting them to the main body of routes.

Like others have said, it’s getting hard to find any unridden roads locally. I have to drive an hour to a start location if I want to ride something fresh. Worth it though.