Things to Do in Boston This September: Live Music & Comedy

Things to Do in Boston This September: Live Music & Comedy City Guides
From Esperanza Spalding's virtuosic jazz at City Winery to Iron Maiden's metal thunder at TD Garden, September in Boston spans intimate singer-songwriters, electronic nights, and stadium-scale rock.

Esperanza Spalding opens the month at City Winery with her genre-defying bass work and sophisticated arrangements, anchoring a September where Boston’s venues showcase everything from metal legends and hip-hop artists to folk singers and electronic producers.

Tip: code GTIX20 takes 20% off ticket prices on every event below — no minimum and no expiry.

Esperanza Spalding

Fri, Sep 4, 7:30 PM · City Winery – Boston · from $159

The virtuosic bassist and vocalist brings her sophisticated jazz-fusion sound to City Winery on September 4th. Spalding’s genre-defying approach—blending jazz, R&B, and world music—makes for an intimate evening of musical exploration that rewards close listening.

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Iron Maiden & Megadeth

Wed, Sep 9, 7:20 PM · TD Garden · from $99

Two metal titans share the stage at TD Garden on September 9th for a night of thunderous riffs and arena-scale production. Whether you’re a longtime fan or curious about metal’s enduring power, this pairing delivers the kind of spectacle that only these legendary bands can command.

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James Taylor & His All-Star Band

Sat, Sep 5, 7:30 PM · MGM Music Hall at Fenway Park · from $78

The folk-rock legend takes the stage at MGM Music Hall on September 5th with a rotating ensemble of guest musicians. Taylor’s catalog spans decades of singalong classics and intimate storytelling, making this a multigenerational draw.

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Don Toliver

Sat, Sep 5, 7:30 PM · TD Garden · from $106

The Houston rapper brings his melodic trap sound to TD Garden on September 5th. Known for his smooth vocal delivery and atmospheric production, Toliver’s live show captures the introspective yet energetic vibe of modern hip-hop.

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Robyn

Thu, Sep 3, 8:00 PM · Agganis Arena · from $82

The Swedish pop innovator performs at Agganis Arena on September 3rd, bringing her distinctive blend of electronic production and emotional directness. Robyn’s live energy and catalog of dance-floor anthems make for a night of pure pop euphoria.

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Sara Bareilles

Wed, Sep 9, 8:00 PM · MGM Music Hall at Fenway Park · from $28

The singer-songwriter and Broadway star takes MGM Music Hall on September 9th with her piano-driven pop sensibility and powerful voice. Bareilles’ music spans intimate ballads and infectious pop hooks, appealing to both longtime fans and newcomers alike.

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Reverend Horton Heat

Thu, Sep 3, 7:30 PM · City Winery – Boston · from $30

The psychobilly trio brings their high-octane rockabilly sound to City Winery on September 3rd. With their signature blend of surf-rock energy and punk attitude, they deliver a night of pure, unapologetic rock and roll.

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Gary Clark Jr.

Thu, Sep 10, 7:00 PM · Paradise Rock Club Presented by Citizens · from $106

The Texas blues guitarist performs at Paradise Rock Club on September 10th, bringing his soulful, modern take on traditional blues. Clark Jr.’s virtuosity and emotional depth make him one of contemporary blues’ most compelling live performers.

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Omar Courtz

Thu, Sep 3, 8:00 PM · MGM Music Hall at Fenway Park · from $238

The Latin artist takes the stage at MGM Music Hall on September 3rd, bringing Caribbean and Latin rhythms to Boston. Courtz’s infectious energy and genre-blending approach create a night of dance and celebration.

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KevOnStage

Sun, Sep 6, 7:30 PM · Citizens House Of Blues – Boston · from $32

The comedian performs at Citizens House of Blues on September 6th with his observational humor and relatable storytelling. KevOnStage’s high-energy delivery and crowd interaction make for an evening of genuine laughs.

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Sam Gellaitry

Wed, Sep 2, 8:00 PM · Paradise Rock Club Presented by Citizens · from $36

The electronic producer brings his intricate, sample-heavy sound to Paradise Rock Club on September 2nd. Gellaitry’s live sets blend hip-hop beats with experimental production, creating an immersive sonic experience for electronic music fans.

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Peter Hook and The Light

Fri, Sep 4, 7:30 PM · Citizens House Of Blues – Boston · from $50

The New Order bassist performs at Citizens House of Blues on September 4th, celebrating the band’s post-punk legacy with a full live band. Hook’s deep catalog and commanding stage presence deliver a night of dark, propulsive electronic rock.

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Check dates and venues carefully—some shows sell out quickly, especially the larger arena acts. Book early to secure your spot.