| City of Laughs | 9-4-2026
Friday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Third Reprise | 9-18-2026
Friday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Music Bingo | 9-19-2026
Saturday
12:00 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| R&B Sing-Along: Sing Your Soul Out with Rey Royale | 9-19-2026
Saturday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Curyman II | 9-22-2026
Tuesday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Fielder | 9-27-2026
Sunday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Lauren Minear | 9-29-2026
Tuesday
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 |
| Hannah Jones | 10-4-2026
Sunday
8:30 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 |
| Music Bingo | 10-17-2026
Saturday
12:00 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 |
| 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 |
| Jack O'Neill | 11-17-2026
Tuesday
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 |
| Music Bingo | 12-19-2026
Saturday
12:00 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
