No. No. Do Not Do It. The first taste of it, and your horse will never, ever forgive you for 1) not doing it earlier, and b) not doing it more often than dressage. I warn you, they do not like to come back to 20 metre circles and lateral work off the rail after they have been to a competitive trail event (even though dressage and trail riding are great for each other). You will get the Arab Glare of Disdain, and if you haven’t already gotten this look, being as your horse is a gelding and not a mare, your horse will now learn it from an Arab mare on the trail.
I only regret not having had the courage/oomph to leave kids with hubby and do more CTRs (shorter endurance-ish rides) when my horse was younger; at 25 she doesn’t have the stifles for it now and her owner needs to go on a diet. But she absolutely reveled in the CTR thing. I remember a judge looking at her and saying, “She’s in her element, isn’t she…” Actually, horse would probably tell me that her stifles are just fine for CTR, and it’s dressage that is getting old.
You must give it a try. Life is short. Arrange things for kids and spouse for 36 hours, and go. They will be fine. (Just remember that you will be tired when you get home, whereas they will be waiting to pounce on you and throw you back into mommy/spouse duty. Save some energy for this inevitability.) If there are rides in your general area, there is no reason you have to spend the night, but I will say that camping with my horse, whom I full board so I don’t have the regular intimacy of night check and “good mornings,” is one of my favorite memories.
Oh, and the trailering part is easy. Go get a trailer and admit that the cult has taken you over. It is hard to depend on others for a ride all the time, especially if you have work and kids that force planning for rides to a whole different level.
We never had time to do more than CTRs, due to work and family commitments and there were very few in my area, but they were a blast in every way. So proud of my horse, so happy to be moving out down the trail, friendly helpful people, knowledgeable judges, folks out enjoying their horses of all sizes and shapes and colors… It was great.