This android app was mentioned in
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Press B in the website editor to bring up the background list and see if there's clearer aerial imagery (remember to fix the offset if there is any).
Or record a GPS trace using https://play.google.com/store/apps/details?id=me.guillaumin.android.osmtracker&hl=en_GB - export it in the app, upload to google drive or similar, then download and load the GPX file in the editor.
Best to record when there's less tree cover of course.
I've added a few of biking and hiking trails, and their associated amenities. I find OSMtracker to be easier to use when recording a trail, and lots of amenities (benches, drinking water, picnic shelters, etc). I use OsmANd when I'm just adding a couple things. To use OsmANd for this:
Now I type that all out it looks very time consuming, but in reality it's not too bad.
Edit: Correcting some terminology. Also, this may not be the most efficient way of doing it, I'd be interested in hearing about it if other's have more efficient approaches.
Would be easier if you used a smartphone app to record a GPS trace - I use OSM tracker on Android: [link]
You can walk along the pavements or drive along all the roads, export a .gpx file and use this in the editor to trace the streets/paths.