Jazz Underground Casts A Spell On Dwight Street

New Haven’s jazz scene entered the new year Thursday night in modal, spacey, vegan style, as trumpeter Nick Di Maria and his band lit up The Cannon. 

Twenty people in The Cannon, an Arsenal pub featuring a plant-based menu on Dwight Street, meant that every table in the room was full. As the band played, more people trickled in — families eating dinner, artsy old-timers, teenage jazzheads, and barflies side by side. Jeopardy! played on one corner TV, and Notre Dame battled Georgia in the College Football Playoff on the other. No one watched either.

“We’re gonna be swinging,” Di Maria told the Independent before pausingto tell his bandmates an anecdote about Art Blakey’s Art Blakey and the Jazz Messengers sessions at Impulse! Records. Di Maria is thinking about starting a record label as the next step in the expansion of his Jazz Underground series.

Di Maria founded the New Haven Jazz Underground collective on Groundhog Day in 2019. He organizes jazz nights at The Cannon every other Thursday. The Jazz Underground runs similar series at Café Nine on Tuesdays and at Three Sheets on Fridays.

Reflecting on nearly six years of promoting jazz in New Haven, Di Maria recalled that he’d ​“always been a DIY guy” and was proud to see the ​“fruits of the labor” blossom to this level. For 2025, he said, the Jazz Underground wants ​“more gigs, more crowds, more ears. I love my city.”

The band — made up of drummer Jimmy ​“the Dream” Gavagan, guitarist Anthony ​“Tony” Carabello, and bassist Eneji Alungbe — played compositions from Di Maria’s project, Indigo Seven. It was Carabello’s first time performing at The Cannon, though he’s been playing jazz guitar for seven years. Before that, had been playing violin since he was 4 years old.

Carabello’s Gibson L‑4 and pedals made magic. Only on occasion could you tell that there was even a guitar in the room. Now it sounded like a flute; now like a horn; now like rain. For Carabello, music is a family affair: his brother plays piano and his father is a saxophonist.

On the first track, ​“Portals,” when Di Maria finished his first bout of trumpeting, he stepped away to let the other musicians shine. He would do this on every track — it’s ​“etiquette,” he said, ​“just what horn players do.”

During that first break, Alungbe showed why he’s known as ​“The Master of Disaster,” working frenetically down the full length of the neck on a groovy solo.

Alungbe, who’s been playing bass since middle school, turned to jazz about seven years ago. ​“I liked the amount of freedom it gave me,” he said. 

On ​“Drift,” the third installment in the set, Di Maria stepped off after the piece’s second trumpet part. The tempo shifted down. Carabello’s warbling guitar highlighted Alungbe’s roaming bass as Gavagan held the crew together in slow, measured fashion.

Gavagan had his standout moments, too — like when he took flight for a jovial and rollicking run on ​“Apparition,” the second track.

The Cannon is owned by Kevin Mackenzie, who plays guitar in The Simulators, a New Haven-based ska punk band.

For Di Maria, an Arsenal pub owned by a ska musician opening in New Haven was a stroke of good fortune. ​“I grew up playing ska,” Di Maria said, ​“that’s where I cut my teeth.” Also a soccer fan, Di Maria recalls being welcomed into the community at The Cannon.

Di Maria was briefly part of The Simulators last year but ended up being too busy to play with them regularly. The connection eventually led to the creation of this jazz series. Mackenzie ended up heading out early last night — ​“gotta go to band practice,” he said. Meanwhile, in his bar, the band was just getting started.