| Lauren Minear | 9-29-2026
Tuesday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Isabel Oliart | 9-30-2026
Wednesday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Britt Connors Band | 10-1-2026
Thursday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Josh Joplin | 10-2-2026
Friday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| 80s Trivia Brunch | 10-4-2026
Sunday
12:00 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Hannah Jones | 10-4-2026
Sunday
8:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Rachel Raven | 10-5-2026
Monday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Micky and The Motorcars | 10-6-2026
Tuesday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Adam Paddock | 10-8-2026
Thursday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Song Garden | 10-9-2026
Friday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Anthony Locascio | 10-11-2026
Sunday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Sicard Hollow | 10-12-2026
Monday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Chloe Star | 10-13-2026
Tuesday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Best Not Broken & Lost My Balance | 10-15-2026
Thursday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Savannah Pope | 10-16-2026
Friday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Music Bingo | 10-17-2026
Saturday
12:00 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Feng E | 10-19-2026
Monday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| VCR | 10-24-2026
Saturday
12:00 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Linda Sikhakhane Quartet | 10-27-2026
Tuesday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Toxtricity | 10-28-2026
Wednesday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Uncrowned: A Tribute to Ida Cox | 10-30-2026
Friday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Splendid Torch | 10-31-2026
Saturday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Lily DeTaeye | 11-1-2026
Sunday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Block | 11-2-2026
Monday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| MaryAnne Muglia | 11-3-2026
Tuesday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| JR Richards | 11-4-2026
Wednesday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Frank Maza | 11-5-2026
Thursday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Halley Neal | 11-6-2026
Friday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Josh Rouse | 11-9-2026
Monday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Gauri B | 11-15-2026
Sunday
5:00 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Gauri B | 11-15-2026
Sunday
8:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Jack O'Neill | 11-17-2026
Tuesday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Ryan Demaray | 11-19-2026
Thursday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| R&B Sing-Along: Sing Your Soul Out with Rey Royale | 11-20-2026
Friday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Music Bingo | 11-21-2026
Saturday
12:00 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Corey Staggers | 11-22-2026
Sunday
3:00 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Sirsy | 11-28-2026
Saturday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| BertCcomedy | 11-29-2026
Sunday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Doobie Powell | 11-30-2026
Monday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Tom Hearn | 12-13-2026
Sunday
8:00 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Music Bingo | 12-19-2026
Saturday
12:00 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
