Things to Do in Boston This Weekend: Aug 21–23

Things to Do in Boston This Weekend: Aug 21–23 City Guides
Hip-hop headliners, electronic beats, comedy, and live jazz fill Boston's venues this weekend. From 50 Cent at The Grand to yacht rock nostalgia at Leader Bank Pavilion, there's something for every mood.

Boston’s music scene is firing on all cylinders this August weekend. Whether you’re into rap royalty, electronic dance floors, stand-up laughs, or smooth jazz, the city’s top venues have lined up a diverse slate of performances that’ll keep you entertained from Friday night through Sunday.

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

50 Cent at The Grand Boston

Fri, Aug 21, 10:00 PM · The Grand Boston · from $46

The Queens rap legend brings his catalog of early-2000s hits and newer material to an intimate Boston venue. Expect high energy, crowd participation, and all the tracks that defined a generation of hip-hop.

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Jack Harlow at MGM Music Hall at Fenway Park

Fri, Aug 21, 7:30 PM · MGM Music Hall at Fenway Park · from $17

The Louisville rapper and singer-songwriter known for “First Class” and collaborations with Lil Wayne takes the stage at Boston’s premier music hall. His blend of rap, singing, and charisma makes for a dynamic live show.

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Isaiah Rashad at Citizens House of Blues

Fri, Aug 21, 8:00 PM · Citizens House Of Blues – Boston · from $42

The Chattanooga rapper and TDE affiliate delivers introspective, soulful hip-hop with live instrumentation. His shows are known for intimate connection and smooth, laid-back vibes that showcase his lyrical depth.

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Yacht Rock Revue at Leader Bank Pavilion

Fri, Aug 21, 7:30 PM · Leader Bank Pavilion · from $9

A fun, high-energy tribute to the smooth sounds of the ’70s and ’80s—think Hall & Oates, Toto, and Michael McDonald. Perfect for a nostalgic night out with friends under the summer sky.

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Kyle Kinane at Laugh Boston

Fri, Aug 21, 7:00 PM · Laugh Boston · from $61

The stand-up comic known for his deadpan delivery and absurdist humor brings his unique perspective to Boston’s comedy hotspot. Kinane’s sets are unpredictable, funny, and deeply personal.

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Meduza at Royale Boston

Fri, Aug 21, 10:00 PM · Royale Boston · from $69

The Italian electronic trio known for infectious dance tracks and remixes takes over Royale’s dance floor. Expect euphoric house beats, crowd energy, and a night of pure electronic bliss.

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Crankdat at Big Night Live

Sat, Aug 22, 10:00 PM · Big Night Live · from $38

The electronic producer and DJ brings bass-heavy, high-octane dance music to one of Boston’s hottest venues. His sets blend dubstep, trap, and house for a late-night dance experience.

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Compaq Big Band at City Winery

Sun, Aug 23, 7:30 PM · City Winery – Boston · from $45

A full big band ensemble delivers swinging jazz standards and original compositions in an intimate wine-bar setting. Perfect for a sophisticated evening of live music and good company.

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Jutes at Paradise Rock Club

Sun, Aug 23, 7:00 PM · Paradise Rock Club Presented by Citizens · from $42

The Boston-area hip-hop artist performs at the legendary Paradise Rock Club with In Color. A hometown show featuring local talent in one of the city’s most storied music venues.

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Robyn Schall at Wilbur Theatre

Sun, Aug 23, 3:00 PM · Wilbur Theatre – MA · from $42

The comedian and actress brings her sharp, observational humor to the historic Wilbur Theatre. Schall’s comedy tackles modern life with wit and relatability that resonates with diverse audiences.

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Venues fill up fast on summer weekends—check dates and book your tickets early to secure your spot. Boston’s got the lineup; now it’s your move.