Upcoming Events (15)
Happy Couples Game Show
The Happy Couples Game Show arrives at City Winery Boston's Haymarket Lounge for a playful, romance-flavored night of trivia. Four couples per round tackle wacky questions to reveal what their partners really think, with the audience joining the interactive fun.
An Evening with Chelsea Berry
City Winery Boston presents Chelsea Berry for an intimate evening at the Haymarket Lounge. Enjoy a songwriter-rich folk set with soulful vocals in a warm, up-close venue—perfect for fans of heartfelt originals and storytelling.
Jill Andrews
City Winery Boston presents Jill Andrews performing live at the Haymarket Lounge on June 3. From her The Everybodyfields days to solo work and Hush Kids, she delivers melodic, genre-bending songs driven by honest lyrics in an intimate, high-energy evening of contemporary singer-songwriter music in Boston.
Family Feud Game Show
A live Family Feud‑style game show at City Winery Boston’s Haymarket Lounge. Hosted by The Entertainment Nation, the interactive evening pits teams in fast-paced survey rounds, with audience participation, playful banter, and plenty of crowd-pleasing moments. Family-friendly fun.
MUTLU
City Winery Boston presents Mutlu live at the Haymarket Lounge on June 19 at 7:30pm. A Philadelphia soul-influenced artist, Mutlu delivers intimate grooves that connect with every listener, following tours with Amos Lee and an opening for Joe Jackson. An engaging, urban soirèe in Boston's City Winery.
R&B Singalong w/ Rey Royale & Friends
Join Rey Royale and friends for an R&B singalong at the Haymarket Lounge in City Winery Boston. A lively, casual music experience where soulful favorites and crowd-pleasers get everyone singing along in a stylish indoor venue.
Caleb Caudle & The Sweet Critters
Caleb Caudle & The Sweet Critters perform in the Haymarket Lounge inside City Winery Boston on June 25, 2026 at 7:30 PM. An intimate Americana-tinged folk concert in a stylish winery setting with warm harmonies and storytelling.
Jazmyn W: The Soft and Dangerous Tour
Jazmyn W headlines a stand-up night at the Haymarket Lounge, City Winery Boston, on her The Soft and Dangerous Tour. The set blends vulnerability with razor-sharp wit as she riffs on dating, divorce, motherhood, and being a fearless, feminine comic. A bold, intimate evening in a sleek, urban venue.
Elijah Scott
Elijah Scott headlines a night at the Haymarket Lounge inside City Winery Boston, delivering country-Americana storytelling with a modern, soulful edge. Expect intimate performances of tracks like Cigarettes and Turnin Into Something, blending small-town roots with urban rhythm in a lively, singer-songwriter setting.
MUSIC BINGO 80s, 90s, 2000's and today!
Join a lively afternoon of music bingo at the Haymarket Lounge, City Winery Boston, featuring hits from the 80s, 90s, 2000s and today. Sing along to favorite tunes as you mark your cards for a chance to win prizes in a casual, social atmosphere.
Macey Isaacs Looks Alive Tour
City Winery Boston presents Macey Isaacs for her Looks Alive Tour at the Haymarket Lounge on July 18, 2026 at 7:30 PM. A nationally touring stand-up comedian from Austin, Isaacs has appeared at Netflix Is a Joke festivals and opened for Tom Segura and Dusty Slay, delivering sharp humor in an intimate club setting.
Noah Richardson Live in Boston
Noah Richardson brings alt singer-songwriter charisma to Haymarket Lounge at City Winery Boston. This intimate live show features catchy tracks and soulful storytelling, anchored by his rising hit Tangerine and a polished, energetic performance in a chic Boston venue.
R&B Sing-Along “Sing Your Soul Out” With Rey Royale
R&B Sing-Along with Rey Royale at City Winery Boston's Haymarket Lounge. An energetic crowd-driven evening of soul and classic R&B, with a playful 'Battle of the Sexes' theme that invites everyone to sing along.
MUSIC BINGO 80s, 90s, 2000's and today!
Join us for Music Bingo at Haymarket Lounge in City Winery Boston. Spin through rounds featuring hits from the 80s, 90s, 2000s and today, sing along, and win prizes in a fun, interactive night of rhythm and laughs.
Songbird: Halley Neal sings Fleetwood Mac
Halley Neal performs a Fleetwood Mac tribute at City Winery Boston’s Haymarket Lounge, delivering faithful renditions of classic hits with warm vocals and lush arrangements in an intimate wine-bar setting. Fans of classic rock will enjoy the melodic storytelling and polished live instrumentation in this autumn-evening concert.