Prince’s 1999 made its Phish debut (appropriately) at this show and included dancers on stage and synchronized steps from Trey and Mike, who wound up lying on the stage with the dancers surrounding them. Weekapaug and Runaway Jim subsequently featured 1999 teases; Jim also included Auld Lang Syne teases. Hydrogen contained Albert teases from Trey. For this show, the Holiday Run dancers’ costumes included a devil, a prostitute, and a pimp. The band jammed Runaway Jim until just before the New Year. The dancers reappeared throughout the crowd and handed out thousands of glowrings to the fans just before a grand balloon drop and pyrotechnics display at midnight. The band counted the crowd into the New Year before busting into Auld Lang Syne. While some fans used the glowrings to start a Glowstick War during Hood, others used them to create long chain links of rings spanning the venue from end to end.

The debut of Grind featured Tom Marshall on vocals and was dedicated to Phish fan Chris Heinel, who had recently been injured in a lacrosse accident. Possum included Wipe Out teases. For this show, the Holiday Run dancers were dressed as nymphs.

2001 included Crosseyed and Painless and Manteca teases. For this show, the dancers on-stage were dressed as flowers, with one dressed as a turkey.

For the first show of the Holiday Run, the stage was decorated with flowers and sculptures. During the encore, parts of the set began to grow and sprout leaves. This stage setup was used for this show only, and disappeared for the rest of the run. Before Sleep, Fish’s drum kit was moved to allow the crew to roll out a small mini-stage with a scaled-down drum set and a baby grand piano. Trey and Mike sat on stools and both played acoustic guitars. This acoustic set-up was used for Sleep, Albuquerque, and Driver. During the Wolfman’s jam, three people in inchworm-like costumes came on stage and danced for the rest of the set. Bowie included a tease of the theme from The Godfather.