Welcome Aboard from the Peach State!
There's a wealth of knowledge and experiences here and the folks here can point you in directions that might work for you.
As far as .380's go, they'll work and better than not carrying at all. A good fanny-pak or small 'tactictal-style' carry pack might work for those long trail runs. Pointless it is not.
LOTS of similar sized 9mm's around. Kahr's come to mind right off but others here will have a few more models posted for you to think about as well.