Tough question. What I\'m finding is that my greatest concert experiences are not necessarily the greatest concerts that I\'ve been to, although the quality of the concert itself is certainly a huge factor. A lot of this has to do with personal connection to the show, surrounding factors, time of life, etc.
3. Berkfest 1999. My first fest. Only 1500 people there. Had crazy jam sessions every night with other guests and with a lot of people from the bands. Everyone just came out at night with instruments and jammed in the campground. Jam sessions were big at fests back then. Felt like I knew half the people there by the end of the weekend. Got in free working with Ben and Jerry\'s. We brought 10 people from our store so we had a very tight crew, we barely had to work with so many of us, and we had a very cushy campsite. Seeing all of my favorite New England jambands in one weekend completely blew my mind. (Percy Hill, Miracle Orchestra, The Slip, Jiggle the Handle, Addison Groove Project). Awesome time.
2. Phish 11/27/98 Worcester Centrum. My 3rd Phish show, got 7th row center from PTBM, start of senior year of high school. It was the right time and a lot of good things aligned. I had been listening to Phish since \'91 but this was the moment when the switch got flipped for me to get hooked on seeing live Phish. Went with some awesome new Phish friends that I had just made (my first real Phish friends), and Phish played an all-time great show. Great experience.
1. Psychedelic Breakfast 5/5/01 Baker Quad; UMass, MA. I was in charge of the QuadFest and PB was the culmination of 14 bands over the course of the day and a ton of work for me over the semester. This was also the culmination of 2.5 years of the band playing incredible shows on campus at UMass. (They started playing the Northampton clubs after this show.) It was also the culmination of me and all my friends living in Baker and Butterfield dorm for two years before splitting up into off-campus housing. This was also the biggest Breakfast show ever at the time (400-500 people) and became PB\'s first live CD release. I\'m not sure if this experience can be topped for me.
I\'ve been to other shows that were greater as pure concerts or events. Big Cypress, Bonnaroo \'02 (first one) and \'09, Phish 3/6/09, PB Butterfield 11/19/99, PB @ Camp Creek \'01, PB Freakout playing Lawn Boy, Phish 12/31/10, probably more. But best total experience involves a lot of factors.