The story of the Pioneer Social Club, better known as just the Pioneer Club, has a “once upon a time” air about it, because the conditions that allowed it to flourish seem so improbable today.
The Pioneer Social Club occupied a former rooming house on Westfield Street, a side street off Tremont near Camden that ran north for a half-block and ended in an alley. Across the street was a transit authority maintenance yard, and according to the City Directory, the Pioneer was the only address on Westfield. It wasn’t the sort of place you walked past. It had to be your destination.
The Pioneer Club was private, and it charged a membership fee, and as such, it could serve liquor after the regular nightclub closing time. But the Pioneer operated as a bar, selling liquor and not just serving it, and for this, the Pioneer needed friends in the city bureaucracy, and it had them.
Imagine: Duke Ellington and Louis Armstrong, together for one night only, at the Pioneer Club! One of the better jazz stories handed down in this town involves the meeting of these two giants at the Pioneer Social Club, on Westfield Street. Neither the club nor the street have existed for years, and all involved have passed, so we’ll never know if the story is true. But I choose to believe it.
Westfield Street ran one short block north off Tremont Street in the South End, between Camden and Lenox Streets, in a mainly African-American neighborhood. The Pioneer Club was in a nondescript building on Westfield, and it was perhaps the most famous after-hours club in a city that once had many. There was a bar and a kitchen on the first floor, and a room with a small stage and an upright piano upstairs. The club was by no means a secret, but most of Boston was completely unaware of its existence, which was just fine with the ownership.
The Pioneer was a private club, not subject to the regulations governing public nightclubs. And it is where the musicians and entertainers went to relax after their own work was done.