By bike-getting out from cities where you lived

Cycling friend and I were talking last night. She does bike touring on her own as well as regular riding around town.

One of the things that often comes up with bigger cities (or maybe smaller ones too that are car-dependent), is for cyclists to find efficient, safe routes to bike out from city core area to the country. Having right wayfinding signs for cyclists can be a problem --even when a municipality promotes a bike route of some distance.

The other option is intercity commuter trains that allow bikes which can avoid dangerous/crappy/circuitous road routes and get cyclists out to the edge of a city or near next city from which they can bike. She told me of her nightmarish experience trying to bike out of downtown Montreal and going east.

To get out of Toronto from downtown, going west, east or north into the country, can be long and means joining several routes. Or one can take a commuter train and now interurban buses with bike racks.

Vancouver it takes some time to go east into the "country" or south to the U.S. Again joining several major on road bike routes, some busy intersections.

How easy is it to bike from the centre of the cities where you live/lived into the country to go on a bike trip to next destination/city/town/site? Is it easy for cyclists to get lost because a safe/good routes are circuitous?