He had a series of shows he called "Midnight Rambles" at his barn in Woodstock and he would play with his band and special guests. It was basically like attending a kegger at your good friend's house, if your friend was Levon and he had a great band and the coolest barn that was both a residence and a performance space/recording studio. It was BYOB and there was a big potluck table where people brought food to share. It couldn't have been a more relaxed setting. Maybe 100 people or so. It felt like hallowed ground to us.
During the regular Midnight Rambles there were no pictures allowed, and Levon was nice and gracious but didn't mingle a lot, understandably, as everyone wanted to talk to him. His kitchen was right off the main room and he would enter from there to take the stage. After attending the first one we noticed that he had a knack for finding all the ladies on his route to the stage and giving them a nice little squeeze, hug and/or kiss as he walked by, so of course we positioned ourselves there for future visits and my wife and a few friends were lucky enough get a little Levon lovin' a few times.
The Kids' Ramble was a little different. It was like going to Grandpa Levon's house, as he mingled with the kids the entire time and really couldn't get enough of them. Pictures were allowed and we got a lot with him; he stopped and chatted with my girls for several minutes and graciously posed for pics. My youngest daughter was only a year old at the time and I'll never forget him playfully whispering her name in her ear repeatedly as he posed for pictures, saying "We gon' dance tonight!" with the biggest, warmest smile that characteristic drawl that just melts you.
So happy we got to do that, and I would give anything to be able to have that experience again.
I still vividly remember standing maybe ten feet from him when we was sitting on the stool at the front of the stage for the "Atlantic City" opener. It was all dark except for a single spotlight on him for the first verse, and then when the band kicked in behind him the houselights came up. It was magical. Getting goosebumps again now as I type--and a little misty again...