Here is what Milo told me before we left: that Burlington in June was "extremely his scene," that he had "a sense of the layout," and that the Jazz Festival was, quote, "not really a ticketed thing, it's more of a vibe that's just happening around you." He said this with the confidence of a man who had looked at one Instagram story from someone who had been there once.
I want to be clear that I brought a jacket. I am not the problem in this story.
We drove up from Montpelier on a Tuesday, which Milo had selected because he'd read somewhere that weekday festivals are "less crowded and more authentic," a sentence I have since added to my personal list of male phrases that mean nothing. The morning was genuinely beautiful — that early June thing where the sun is absolutely lying to you, all warmth and promise, while the air coming off the lake is still firmly in a different season. Sixty-two degrees. I was fine. I had the jacket. Milo was in a short-sleeved linen shirt he'd described as "breathable," which is a word that also means "cold."
We found Church Street immediately, which was the one thing that went according to plan.
Then Milo stopped walking.
In the middle of Church Street, coming directly toward us, was a tree. A full tree. A forty-eight-foot black locust tree on some kind of flatbed situation, being walked through downtown by what appeared to be a large and completely unbothered procession of people. It was going very slowly. It was taking up the whole street. There were detour signs. There were orange cones Milo had already walked around without registering as meaningful information.
He watched the tree for a long moment.
"Is that," he said, "part of the jazz festival?"
It was not part of the jazz festival.
It was, I later read on my phone like a person who looks things up, a public art procession. Planned. Announced. Very much a known thing that was happening today, on the specific day Milo had selected for our visit, in the specific location Milo had identified as our starting point. I showed him the article. He read it. He nodded slowly, like a man receiving news about weather in a country he doesn't live in.
"Cool," he said. "So the jazz is somewhere else."
The jazz was, in fact, everywhere, which was the whole point, and also somehow the source of every problem that followed. Milo's system for locating free outdoor performances was to walk toward whatever sounded like music and then assert we were "basically there" at intervals that did not correspond to any measurable decrease in distance. We found a set we liked near the waterfront, which was excellent, and I was happy, and then Milo said he wanted to find "the main stage" and I made the mistake of not immediately sitting down and refusing to move.
There is no main stage. Or there is, but it rotates. Milo spent forty minutes developing a theory about this that I cannot fully reconstruct but involved the detours from the road construction, the tree, and a strong suspicion that we had been walking in a very large circle, which we had.
We ended up at Sweetwaters, which had apparently just reopened after four years away, and the woman at the door said "welcome back" in a way that was clearly meant for the restaurant's returning regulars but which Milo received as personally directed at him. "Thanks," he said warmly, as if he had been coming here for years and had simply been away.
He had never been to Burlington before in his life.
He ordered something and pulled out his phone and showed me a TikTok about how 2026 is the new 2016, how everyone's nostalgic for the last time things felt messy and communal and unoptimized. "This is literally what today was," he said.
I looked at him across the table. He was still a little cold. He had taken a small paper napkin and folded it into a rectangle and tucked it into the collar of his linen shirt like a scarf.
He was completely sincere. He really did think today was exactly that.
The thing is — and I will not tell him this, because he doesn't need the encouragement — he was sort of right.