| The Ike Reilly Assassination | 3-5-2026
Thursday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Jam Band Night | 3-7-2026
Saturday
7:00 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Comedy and Cabernet | 3-13-2026
Friday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Ava Val | 3-14-2026
Saturday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Andrea von Kampen | 3-15-2026
Sunday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Brendan James | 3-18-2026
Wednesday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Music Bingo | 3-21-2026
Saturday
12:00 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Rey Royale | 3-21-2026
Saturday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Alex Hamburger | 3-22-2026
Sunday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Ben Katzman's Degreaser | 3-27-2026
Friday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| VCR - Vernon C. Robinson | 4-1-2026
Wednesday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Sarah Potenza | 4-5-2026
Sunday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Jane Siberry | 4-9-2026
Thursday
6:00 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Jane Siberry | 4-9-2026
Thursday
8:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Comedy and Cabernet | 4-10-2026
Friday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Flower and Ash: A Post-American Concert | 4-16-2026
Thursday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Music Bingo | 4-18-2026
Saturday
12:00 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| JFDR | 4-19-2026
Sunday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Your Neighbors | 4-23-2026
Thursday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Charles Langford | 4-24-2026
Friday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| The Neon Queen - All The Girls, All The Hits, All The Stars, All The Fun | 4-25-2026
Saturday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Adam Mamawala | 5-1-2026
Friday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Sol Sesh Live by Tolieth | 5-5-2026
Tuesday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Paris_Monster | 5-15-2026
Friday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Music Bingo | 5-16-2026
Saturday
12:00 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Comedy and Cabernet | 5-16-2026
Saturday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Dan Rodriguez | 5-17-2026
Sunday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Sol Sesh Live by Tolieth | 6-9-2026
Tuesday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Comedy and Cabernet | 6-12-2026
Friday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Mutlu | 6-19-2026
Friday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Music Bingo | 6-20-2026
Saturday
12:00 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| R&B Sing-Along: Rey Royale and Friends | 6-21-2026
Sunday
12:00 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Jazmyn W | 6-26-2026
Friday
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 |
| 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 |
| Music Bingo | 8-15-2026
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 |
| 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 |
