City bikeshares are a great way to get around if your town has them. But they're only convenient as long as:
There are stations near you and your destination, since you'll be walking to and from there
The route in between isn't awfully hilly, because you'll be on a bike
Revisiting Duncan's excellent demo last week, we've refined a trip planning app for DC's bikeshare system. To plot a route, drag the figure and star markers to your origin and destination, respectively. Then click "view elevation profile" to get a sense for the dips and bumps you'll find along the way.
Mapbox's bag of tools is particularly suited for spatial analyses like this. Given endpoints of a trip, Turf.js can find the nearest bikeshare locations to pick up and drop off your bike. Smart Directions then plots a route to guide you there, and Surface provides elevation readings at regular intervals along the path.