| Elijah Scott | 7-3-2026
Friday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| The E-Block | 7-9-2026
Thursday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Musicians Playground | 7-10-2026
Friday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| The One Night Stands Acoustic Brunch | 7-12-2026
Sunday
12:00 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Gabe Lee | 7-12-2026
Sunday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Sol Sesh Live by Tolieth | 7-14-2026
Tuesday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Brad Byrd | 7-16-2026
Thursday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Julia Shiplett | 7-17-2026
Friday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Music Bingo | 7-18-2026
Saturday
12:00 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Macey Issacs | 7-18-2026
Saturday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| King Garbage | 7-19-2026
Sunday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| King Kyote | 7-24-2026
Friday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Elisa Smith | 7-25-2026
Saturday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Rushil | 7-26-2026
Sunday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Noah Richardson | 7-31-2026
Friday
8:00 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| The Tano Jones Revelry | 8-14-2026
Friday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Music Bingo | 8-15-2026
Saturday
12:00 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Comedy and Cabernet | 8-21-2026
Friday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Matt Corman | 8-27-2026
Thursday
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 |
| Adam Paddock | 10-8-2026
Thursday
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 |
| 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 |
| Halley Neal | 11-6-2026
Friday
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 |
