When the Trinidad Lounge opened in November 1958, the Boston jazz club scene was in transition. Nineteen fifty-five had represented a high point, and although the music was by no means scarce in 1958, it was on the decline. Perhaps the Hi-Hat’s abrupt alteration of its schedule in 1955, explored here, was a harbinger of that.

Ad for Trinidad Lounge, 1958

Grand opening of the fabulous Trinidad Lounge. That’s one weird turtle.

Clubs were making the turn from jazz and standards-based pop to folk, R&B, and rock to attract a new generation of club-goers. No one was more aware of these changes than George Wein. In 1959, Storyville was losing money and Mahogany Hall was open only on weekends. He converted Mahogany Hall to the Ballad Room, a folk club, and closed Storyville in 1960. Change was in the air, and the Trinidad Lounge, a barroom with palm trees painted on the walls, was part of this transition.

The Trinidad Lounge, located at 1844 Washington Street in a low-rent part of the South End, stood in the shadow of the elevated tracks, near the Northampton station. There it joined Louie’s Lounge, at 1788 Washington, a onetime jazz club that probably turned to an R&B policy by 1957. It’s hard to say because Louie’s did not advertise in the 1950s. The Trinidad did, and it opened with a splash.

A jazzman, pianist Hopeton Johnson, led the house band at the Trinidad, but he didn’t play much jazz. His band, the Hurricanes (Harvey Williams, tenor; Ricky Gale, bass; Isaac Allen, drums) played R&B and rock and roll. Della Thomas, a former gospel singer, fronted the Hurricanes. During their time at the Trinidad, the group recorded a 45 on the Monitor label under Thomas’s name, “Let It Roll Everybody,” which became a local hit.

Jazz wasn’t completely absent from the Trinidad Lounge; “soul jazz” organ trios and quartets worked there, and their Sunday afternoon jam sessions were still popular in 1959.

Starting in the fall of 1959, Sabby Lewis had the house quartet (trumpeter Phil Edmunds, bassist Jerry Edwards, and drummer Vic Derry) and probably played some jazz when nobody was paying attention. Mostly, though, Sabby backed singers—up-and-coming soul singers mainly, like Jean Sampson and Debby Moore, but also R&B veterans like Etta James and Varetta Dillard. This policy continued until the club closed in May 1960.

The property at 1844 Washington Street stayed vacant until the end of the year, when Basin Street South opened on New Year’s Eve—and burned down three weeks later. It reopened in September 1961, and although it booked some big jazz names in its early years, the club was better known for presenting the Supremes, Marvin Gaye, and Dionne Warwick.

Louie’s Lounge, in the early 1960s, was booking names like Jackie Wilson, Mary Wells, and Gene Chandler. A third club, the Shanty Lounge, opened under the elevated in June 1961, at 1781 Washington, with an organ-trio-plus-special-guest policy, but it also migrated to soul and R&B.

In the 1960s, Washington Street was where you went to hear what had become mainstream black music. The soul singers at the Trinidad Lounge were on the front end of that transition.

As a side note, among the musicians leading house bands at these clubs in the early/mid 1960s were pianist Dave Burrell, then a Berklee student, at Louie’s Lounge, and keyboardist Bernie Worrell, then an New England Conservatory student, at Basin Street South.