I trailer just about every place I ride. I have trails that are as close as 10 minutes to 30 minutes to an hour away depending on what I want to ride or who I go ride with. There could be some riding from my house, but it isn't very good. A lot of traffic and just too much going on. Plus the horse I may be riding can hear her buddies calling so it hard to keep the riding one's attention.
I like the flexibility of trailering as I have about 10 different places within 30 minutes or less to go ride. Helps keep me and my horse from getting bored. Plus I can pick where I want to go depending on how much time I have, what the weather is like or what type of ride I want to do, flat, hills, etc...