By the summer of 1986, the Grateful Dead were deep into one of the more complicated chapters of their long run. Brent Mydland had by now fully shed his early tentativeness and was playing with a muscular, gospel-inflected confidence that pushed the band into heavier, more urgent territory than the Keith Godchaux years. Garcia's health had become a quiet but growing concern among the inner circle — he would collapse into a diabetic coma just weeks after this show in July, casting a shadow over the whole year — which makes recordings from this stretch of 1986 carry a particular weight in retrospect. The band was still capable of extraordinary nights, and summer shows in the Midwest often brought out a loosened, festival energy that suited them well. Alpine Valley Music Theatre, nestled in the rolling glacial hills of East Troy, Wisconsin, was already establishing itself as one of the Dead's beloved outdoor amphitheater stops. The natural bowl setting gave the sound room to breathe, and the Upper Midwest crowd had a fervor that rivaled anything you'd find on the coasts. The Dead returned here repeatedly across the '80s and into the '90s, and fans from Chicago, Milwaukee, and beyond would make the pilgrimage out to that hillside with a devotion that said everything about what these summer shows meant. The songs we have from this date offer a tantalizing window into the setlist.
An "Estimated Prophet" into anything is reason to pay close attention — its irregular 7/4 groove creates a kind of trance-inducing pressure that the band could either ride to transcendence or lose momentarily, and by 1986 they had developed a real authority with it. "Eyes of the World" flowing out of "Estimated" was a classic pairing, the shift from Bob's grinding prophetic churn into Jerry's warm, jazz-touched melody like stepping out of a storm into golden afternoon light. "U.S. Blues" showing up suggests a bright, celebratory moment, probably a first-set closer waving the flag with that knowing wink Garcia always brought to it. Listen for the way Brent and Jerry lock up harmonically during the "Eyes" jam — by this era, Brent's organ was a genuine second voice in those excursions rather than mere texture. If a soundboard source is circulating from this date, the mix from Alpine was often excellent; even a clean audience tape from this venue captures the natural reverb of the hillside beautifully. This is a show worth your Sunday afternoon.