First to get an idea of what dedicated cycling infrastructure is available on your route, check out the Dane County Bicycle Map. Separated paths are highlighted in Lime Green. Streets highlighted in Jungle Green or Blue are recreational routes and bike boulevards. These routes may have some separated paths and are also the safest on-street routes for cyclists with features like diverters which make the street one-way for cars but two-way for bikes. Brown indicates streets with bike lanes, though these might not be suitable for all ages and abilities.
Google maps is pretty good at choosing comfortable cycling routes from A to B when you tell it to design a route for a cyclist. Google maps also has layers (toggle is bottom left corner on PC, upper right on mobile) which you can use to highlight cycling specific infrastructure. If you are traveling somewhere in Madison you haven’t been before, you can also look at the city’s Low-Stress Bike Route Finder to see if you are likely to be comfortable on those streets.
