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Maybe try getting in from the outfall or infall points instead. From my experience they lead much farther distances. Also, if you're lucky you may be able to find a map of the storm water/sewer utility in your city, showing the routes you can take beneath the ground. In my city the busy streets often have the longest drains which go on for miles, but getting in via manhole is nearly impossible. In fact, I have never even come across a dead end in my city yet. I either only explore the ones I know the route of to be large, or I just haven't gone deep enough in there.

99% of the time (especially in an urban area) popping manholes leads to small water ways that you can't even crawl through

I can highly recommend a walk by a nearby river or creek if there is one in your town. This can help find many good outfalls.

If you crawl through ones that are super small and tight we may never hear from you again...

I'm very into exploring storm drains. I often find storm drains by looking on Google Earth and driving around when the weeds and trees are dead during the wintertime. MSP has a lot of nice drains to explore. If you find any outfalls that have gates on them, try looking for nearby manhole covers, then pop those covers to see if they are for that drain. There are a lot of times where if an outfall has a gate, then you might be able to squeeze in an opening underneath the gate to get into the drain. Always look by rivers, lakes, creeks and ditches to find drains, then what I do is get an address from a nearby building and make sure it's not an issue to park your car there. It can be a lot of fun to look on Google Earth for drains and manhole covers.

Aside from what the others above me have said (look along major waterways), the other best way to find good drains is to see if your city has a publicly viewable stormwater GIS map. If they have one and you can view it, most stormwater GIS maps show the drains themselves along with the diameter of each section, so you can get a better feeling for what you're looking at. Some even show manholes. It's a very useful tool.

Posted by Aran Aside from what the others above me have said (look along major waterways), the other best way to find good drains is to see if your city has a publicly viewable stormwater GIS map. If they have one and you can view it, most stormwater GIS maps show the drains themselves along with the diameter of each section, so you can get a better feeling for what you're looking at. Some even show manholes. It's a very useful tool.

That's very true.