There are many different ideas about this, I’ll throw
in mine.
If I approach a horse from behind and I’m gaining
steadily and there’s room to safely pass, I announce I’m “passing
on the left/right” . If there’s no room, I usually wait a bit to
see if they are going to offer the trail, if not then I ask them to pull over
when there’s a spot to allow me to pass. None of this happens too often
as I don’t ride with any particular placement as a goal, but I also want
to be able to ride at my pace, not someone else’s. The only time I had
any difficulty with this was in the dark on a single track trail that I knew
and the riders in front didn’t know well enough to go faster or to pull
over. It took consistent nagging to get them to at least just stop in the
middle of the trail so I could go around them.
If I’ve ridden up from behind and then I don’t
want to pass, my horse or I just need some company, I do usually let the rider
ahead know I’m just going to hang back for awhile, as long as it’s
not bothering their horse. If they don’t want that, they’ll either
pick up the pace or insist on pulling over and letting us by. I don’t
think that’s drafting off another, nor asking for permission to be back
there, just letting them know what my intentions are and if they don’t
like it, they can voice their preference.
I try to pay attention to what’s going on all around,
just like driving. So if I feel someone gaining steadily, I’ll ask if
they want to pass, and look for a safe place to pull over. If they don’t
want to pass but their presence is annoying my horse (my mare is particularly
bothered by boys behind her) then I’ll announce “I’m going to
pull over so you can pass because my horse is bothered, blah, blah, blah. If
they want to stay together, then I ask them to stay at least 3-4 horse lengths behind
(or whatever is required for my horse to stop her “I’m really
annoyed” behavior), and explain that my horse doesn’t like unknown
horses close behind. I’ve never had anyone not cooperate when I was the
one in front that needed some rear end cushion. I wouldn’t tolerate
someone riding our tail that didn’t want to pass and have never had
anyone continue to ride close when I’ve explained my situation.