I typically use maps, but sometimes it's a bore to plot out trail distances.  Just looking for a quicker/easier way.  Any suggestions?

Would this do the trick..
https://www.freemaptools.com/measure-distance.htm

I usually just use maps myself. However, I use google earth pro all the time for work and it has a path measurement feature. You have to click out the route which takes time but it does work and will even give you the cross section when finished. When I plot out hikes on there I use a USGS topo overlay not the typical google earth overlay. The USGS map overlay will show all the trails clearly (sometimes including some that really don't exist or are grown over IRL), whereas the default google earth overlay will only usually show famous trails like the AT. You can save your path measurements in Google Earth Pro when you are finished. Pro is also free but it installs as a separate program from the regular Google Earth (it looks and works the same but with additional features).

ETA: It appears that you can create and save paths in regular Google Earth as well. (I need the area measurement function for work which only Pro has)

ETA2: Here is a link where you can find the USGS topo overlays. http://www.outdoors.org/articles/amc-outdoors/how-to-add-usgs-topographic-maps-to-google-earth/. The overlays in Google Earth are sometimes disagreeable. IIRC if they wont load, double click on the overlay in the side menu and it should zoom all the way out to the earth in space and then load the overlays. You then need to zoom back in.

Looks like regular old Google maps does it automatically.  This seems like it's on the right track though.