| 80s Trivia Brunch | 4-12-2025
Saturday
12:00 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Sessa | 4-15-2025
Tuesday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Lizzie No | 4-16-2025
Wednesday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Janie Barnett | 4-17-2025
Thursday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Heather Shaw | 4-18-2025
Friday
6:00 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Fabulous Feud Game Show | 4-19-2025
Saturday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| VCR | 4-20-2025
Sunday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Chad Hollister | 4-24-2025
Thursday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Pearl Scott | 4-25-2025
Friday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Dan Rodriguez | 4-26-2025
Saturday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Ariana and The Rose | 4-30-2025
Wednesday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Kyran Daniel | 5-2-2025
Friday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Sea Wolf Solo | 5-7-2025
Wednesday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| The Wildwoods | 5-8-2025
Thursday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Asher Roth | 5-9-2025
Friday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Jimmy Vivino | 5-14-2025
Wednesday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Denitia | 5-15-2025
Thursday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Ross Livermore | 5-17-2025
Saturday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Natalie Cressman & Ian Faquini | 5-18-2025
Sunday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Lauren Calve & Rachel Ana Dobken | 5-20-2025
Tuesday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Ganavya | 5-28-2025
Wednesday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Fellswater | 5-31-2025
Saturday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| California Guitar Trio | 6-2-2025
Monday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Max Muscato | 6-13-2025
Friday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Christian Johnson | 7-6-2025
Sunday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Lala Tamar & Duo Andalus | 7-8-2025
Tuesday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
| Sirsy | 8-31-2025
Sunday
7:30 PM | Haymarket Lounge At City Winery in Boston, MA | View Tickets |
