Riding Alone at night?

It sounds like you'd be riding in an arena at night, right? I ride by myself in the arena at night during the week, for the same reasons as you. I was uncomfortable at first, but got myself used to it by starting a few rides on the weekends at dusk, so that there was some daylight when I started, but it was full dark by the time I finished. After doing that a few times, riding in the dark stopped bothering me as much.

I personally don't have an issue riding at night/in the dark..BO doesnt want her horses being ridden because of the risk though. Since I don't own ST yet and don't know all the trails by heart, I wont do it though. If I were at my old barn, Id be running barrel and pole patterns at night, lol.
I can see relatively well at night and never use a light unless im outside going up/down stone steps (im clumsy with those, lol), so it's never bothered me. I go for walks in the woods at night alone all the time, though Im always armed with a knife or two as well as my personal intimidation factor. Most guys (the creepy ones, lol) wont even come up to me if they get a glance at me in light because Im usually the same size as or bigger than them. I don't worry much about people or animals aside from the occasional bucks, as they're nasty critters. My horse is quite literally bombproof, so even on her I wouldnt worry much about anything. I am scared to ride along the road at night to the trails, as there arent any street lights and cars FLY on that road. If I had access to trails without having to take the road though, you can bet I wouldve convinced BO awhile ago to let me take her out at night, haha.
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I used to ride my now retired horse around the property (gated facility with no arena lights) at night and sometimes at night alone. With my new guy, I do lunging at night and have ridden twice at night, but other people have just so happened to be there. I always ride him in an arena at night (and in general at this time) because he is only 3 years old. I would ride him alone at night though if needed, mainly because the dark doesn't bother me (it's dark, but I can still see), but also because I know somebody will eventually be there to pick me up. I didn't wear a helmet when walking my other horse around the property, but I always wear one when riding the baby and other people's horses.