Interestingly, however, thanks to careful research by an esteemed scholar, it appears that the Dead's first appearance in New York City was actually at Tompkins Square Park, on Thursday June 1. I have seen allusions to the Dead's performance in Tompkins Square Park, but until now I have not had it pinned down. However (h/t Psychlops), a careful review of the June 8, 1967 Village Voice, in a lengthy story about police hassling hippies and free concerts in the city, reveals this paragraph:
June began on Thursday, and the Grateful Dead were in town, and, despite some rumble rumors from the Puerto Ricans, the prospects for peace looked promising. A happy, scruffy parade of 80 marched down St. Mark's Place, complete with police escort, to present the Dead with a white carnation key to the East Village, graciously accepted by Pigpen. And the Tompkins Square bandshell rocked with San Francisco glory until a noise complaint was lodged in the late afternoon. Rather than tune down, the Dead turned off.The link to the article is here--see page 21.
When the Dead had played Vancouver in July and August of 1966, underground legends but with no records to their name, they had hit on the idea of playing for free in a public park to publicize their performances. The performances in Stanley Park in Vancouver actually preceded any free shows in the Panhandle, and as the Dead started to tour they used free shows in public parks to attract publicity. It seems to have worked in this case, and it would work again when the Dead played Toronto and Montreal a few months later.
Tompkins Square Park is a relatively small public park in the East Village, bounded by East 10th Street, Avenue A, East 7th Street and Avenue B. A look at the entertainment section of the Village Voice shows what a happening place it was: the Grateful Dead were playing the Cafe Au Go Go, supported by Toronto's coolest band, Luke And The Apostles. Moby Grape was at The Scene, and The Doors were booked for the following week. Wes Montgomery was at the Village Vanguard, andthe Roy Haynes Quartet was at Slug's, although as always, Slug's on Monday night, Sun Ra held court. Upstairs from the Cafe Au Go Go was The Garrick Theater, and the featured act that Summer was Frank Zappa and The Mothers, with their show "Absolutely Free" (which was not, in fact, free, as at least one visitor from New Jersey discovered). Zappa, of course, was famous for not letting his band smoke pot, a prohibition that was very difficult to enforce with the Grateful Dead performing in the basement. According to Rock Scully, members of the Mothers told the Dead that if Zappa caught them smoking pot, they would be punished with more rehearsal.
So although the Dead were underground legends, the 1967 Village was a happening place indeed, so its not surprising that the Dead had to put themselves out there to make sure that rock fans chose them over the numerous other excellent choices.