The trails we ride sometimes have "transients" around the trail. So far no problems with any of them. Some homeless had a camp along our local trail and several were actually nice. Talked to them when I was doing brush cutting along the trail. Next trip over I gave them a few microbrews and snacks. Two were old Nam vets that just could not fit back into society as we know it. not druggies. Just liked their beer and a free life.

I use pepper spray as my first line of defense. Can't go winging .380 Hydra Shoks around a trail where there might be innocent people not in direct sight.
Keep in mind there are two kinds of pepper spray dispensers. One will throw a stream. The other simply creates a fog only a few feet in front of you.

I bought a sleeve that goes around the top tube and has snaps on it. Then an elastic sleeve with snaps goes around the pepper spray container. I clip a 3 oz. stream sprayer on that. In one of my shirt pockets I will carry a 2 oz fog sprayer.

You don't want to use the fog type in any sort of wind. Position relative to the attacker and the wind is critical. The fog type work on calm days. The stream sprayers I buy at a police supply store will project a thin stream out about 20 to 25 feet with a minimum of droplets outside the stream. Not nearly as sensitive to wind.

I have used the fog type once when a group of youths followed my wife and I. Hanging just off our back wheels making nasty threatening comments. Used the fog type as if I were crop dusting. As soon as they got a taste of the pepper spray in the air behind me they decided that trying to intimidate the old folks was not the best idea nor the fun for their day.

The legal implications of hosing somebody with pepper spray are far different than hauling out the pistol. They only have to voice threats to make the pepper spray perfectly legal.