I've done something similar - and less ambitious - on bike in NYC: I biked all Brooklyn and at this point 90% of Manhattan. I bet Pittsburgh is next-level conf

I've done something similar - and less ambitious - on bike in NYC: I biked all Brooklyn and at this point 90% of Manhattan. I bet Pittsburgh is next-level confusing. But I think the philosophical questions apply anywhere. I enjoyed that as much as the actual endurance, and I loved seeing him dedicate so much time to that. It's not obvious when you start how subtle these questions get. Challenges I remember: - what level of highway counts. Some surface road highways are clearly navigable. Interstates obviously aren't. - on-ramps. When does a local road end and highway begin? What do you do when the ramp is a gradual transition from a local road? - divided roads (i.e. parallel north/south roads separated by a median, highway service roads) - roads that peter out into alleys, sort of go through peoples' property, may be fenced off, may be legal thoroughfares even if fenced off - campus road networks with varying levels of gate access / accessibility - access roads behind apartment complexes that only led to driveways - housing project street grids - park roads, bike paths, walking paths, trails - intersections with distinct turn lanes, plazas in the middle, etc. - highways / bridges only accessible once a year (i.e. dedicated bike tours)