I've done a lot of festivals, they are fun. We've done Bonnaroo, DelFest, Telluride Bluegrass Festival, Red Wing Roots and Music, FarmAid (though that is just one day), among others. We are looking into going to Woodstock in August, their lineup is incredible.
Going to see live music was one of my family's favorite things in my youth, and one of my wife and I's favorite things now. I was a Virginia kid in my teens in the 90's, so I've always been a big Dave Matthews Band fan (they hail from Charlottesville in the 90s). I've seen them at least 30 times since about 1998. Over the years I've seen the Rolling Stones, the Allman Brothers, the Band, Pearl Jam, Stone Temple Pilots, Jack Johnson, John Mayer, Red Hot Chili Peppers, Vampire Weekend, Tom Petty, the Avett Brothers, Jack White, and so many others. God knows how much money I've spent!
The stuff I've enjoyed going to see the most lately are the alt-country singer/songwriters, most of whom come from Texas, that are great and that you can see in medium-size venues where it is a little more intimate. Guys like Ryan Bingham, Robert Earl Keen, Hayes Carll, and the Turnpike Troubadours. They are a lot of fun and some great songwriting chops.