Romantic Events & Date Night in Boston

Sarah McLachlan - Better Broken Tour

Fri, 10 Jul 2026 at 3:30 PM

Leader Bank Pavilion

Music

Sarah McLachlan headlines the Better Broken Tour at Boston's outdoor Leader Bank Pavilion. The show is July 10, 2026, with doors at 6:30 pm and the concert at 7:30 pm; rain or shine. All support acts subject to change. An intimate, melodic evening from a renowned singer-songwriter in an iconic venue.

Air Supply - A Matter of Time Tour

Thu, 5 Nov 2026 at 3:00 PM

The Chevalier Theatre

Music

Air Supply brings its Matter of Time Tour to Chevalier Theatre in Medford for a night of timeless soft-rock and romantic ballads. Expect signature hits like All Out of Love delivered in a warmly intimate venue with polished harmonies and crowd sing-alongs.

Joshua Radin

Thu, 19 Nov 2026 at 3:30 PM

City Winery Boston — Main Stage

Music

Singer-songwriter Joshua Radin brings his intimate, melodic folk-pop to the Main Stage at City Winery Boston. Expect heartfelt tunes from his acclaimed catalog delivered in a warm, wine-bar setting that makes for a personal listening experience.

Maybe Happy Ending

Tue, 2 Feb 2027 at 2:00 PM

Citizens Opera House

Theater

Maybe Happy Ending at Citizens Opera House in Boston is a contemporary theater piece staged in an intimate opera-hall atmosphere. Expect a lush blend of drama and musical storytelling, served by live musicians and expressive performances that fuse narrative depth with operatic sensibilities. A refined, adult-oriented evening of performance.

Coppélia

Wed, 10 Mar 2027

Citizens Opera House

Theater

George Balanchine’s Coppélia, a sparkling classical ballet by Boston Ballet, returns to the Citizens Bank Opera House in Boston for a run March 11–21, 2027. In this playful village tale, charm and mischief collide with precision dancing, making it a vivid, entertaining night of dance.

Cinderella

Wed, 28 Apr 2027

Citizens Opera House

Theater

Frederick Ashton’s Cinderella graces the Citizens Bank Opera House in Boston from April 29 to May 9, 2027. A radiant ballet that blends fairy-tale storytelling with lush orchestration, it showcases luminous dancing, elegant stagecraft, and magical production values that enchant audiences of all ages.

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