One of the joys of traveling with little kids is continually catering to their relatively low endurance, need for naps, and all of the junk (diapers, changes of clothes, snacks) that they seem to require for even short outings. For even the most avid babywearers among us, sometimes a stroller is just a much more comfortable way to go.
In creating this website, one of the things I really tried to seek out was easy places to use a stroller. Paved greenways are relatively easy to find, as Google Maps has a “bicycling” layer that can be activated which includes paved greenways and wide sidewalks (which actually are not always bicycle-appropriate, but are fine for strollers and wheelchairs). Open Street Map also has trails of various types demarcated on its basemap. In both cases though, these organizations are dependent on user contributions to be able to display certain kinds of data on the map.
As a result, a significant amount of greenways, trails, and sidewalks can be missing from the maps if spatial and characteristic data on these facilities have not been submitted by local governments or citizens. So other websites are needed to really get a good idea of what kind of greenway facilities might exist in an area, including local government websites (particularly pages belonging to the parks and recreation, planning, and/or the transportation departments) as well as local citizen, civic, and non-profit groups that highlight pedestrian and bicycle amenities in the area, and trailheads or parking. Satellite photos are useful to double check, as are blogs featuring independent reviews of ped/bike facilities.
In evaluating urban areas to stroll with little ones (i.e. “Walkable Downtowns” as shown by yellow stars on the Regional Destinations Map), typically I start with some satellite photo reconnaissance, first looking for a dense mix of businesses and civic destinations in a relatively small area of a couple blocks, followed by the presence of wide sidewalks on both sides of the street. After identifying promising locations remotely, I then “ground-truth” the geography, often by just walking around (or using “Street View”), paying attention to features like extant and appropriately-placed curb ramps, pedestrian signals, shade trees, benches, patios, street art, human-scaled street lights, and general cleanliness/upkeep of public infrastructure. All of these features together contribute to a comfortable and interesting pedestrian experience.
In more rural areas, I look at National, State, and Local park websites to find out what kind of amenities are present, hopefully with an extended description of conditions. I also look at independent trail and point of interest reviews to find out whether unpaved trails are truly kid-friendly, or wheelchair/stroller friendly. If something is ADA (American Disabilities Act) compliant for people in wheelchairs, it will be stroller accessible too, even if the latter option is not explicitly searchable. The National Park Service includes ADA accessibility in its mission.