#1 Three Places In New England #2 The Unanswered Question #3 The Violin Sonatas 1-4 If your really brave then throw yourself into Symphony #4 and then his AMAZING "Concord" Piano Sonata. His first 2 symphonies are very romantic, but great listening with plenty of Americana woven throughout the pieces. His "songs" are wonderful as well. Once you tune your ear to the genius of Ives, he's quite an infectious composer and character.
Cool. I'll give it a go.
Have you ever experienced the works of Havergal Brian? His Symphony no. 1 "Gothic" is out there.