I'd make sure you really like it here before thinking you'd love it here. My ex couldn't make the adjustment. There is a culture shock. As G.B. Shaw said: "England and America are two countries separated by a common language" :))
I seldom do a trail ride. Revert back to my youth and just ride to someplace. States usually put out a series of county maps with every road, dirt or otherwise, that's maintained by the state or county. And then there's the firelines, logging roads, farm lanes. Many times a local can tell me a shorter way vs riding along the road. For a day ride anyplace within 20 miles is a good destination and there's often more than one route to get me there, so I can use a different route back.
Just can't ride along the interstates (boy could that save some time :)) ). I just wish good places to camp overnight were easier to find at resonable distances. But it's still doable. Obviously, since people still cross the US on horseback (the ultimate "trail ride" :)) )