1) Lucinda Williams at Rosebud in Pit when she was touring the Car Wheels CD
2) Steve Earle at Rosebud in Pit when he was touring the Telephone Road CD,
3) Emmy Lou Harris at Rosebud in Pit touring the Wrecking Ball CD
4) I'll throw in a tossup for 4: between the second time I saw The Cowboy Junkies, at Hartwood Acres in Pit (touring the MFOH CD) about a week before 9/11 happened; or the second time I saw Lucinda Williams, this time at Metrohell in Pit, and I believe still touring the Carwheels CD.
I pretty much don’t include the bigger name concerts I went to in the 70s & 80s as I was usually so intoxicated on something that I never remembered much about them.