| Event | Venue | Date/Time | |
| Avery Sunshine | City Winery - Boston
Boston, MA | Wednesday
4/8/2026
7:30 PM |  |
| Monkeys on a String - Dave Matthews and Tim Reynolds Tribute | City Winery - Boston
Boston, MA | Friday
4/10/2026
7:30 PM | |
| Toubab Krewe | City Winery - Boston
Boston, MA | Sunday
4/12/2026
7:30 PM | |
| Anders Osborne | City Winery - Boston
Boston, MA | Monday
4/13/2026
7:30 PM | |
| Grag Queen | City Winery - Boston
Boston, MA | Tuesday
4/14/2026
7:30 PM | |
| David Cook | City Winery - Boston
Boston, MA | Wednesday
4/15/2026
7:30 PM | |
| Bill Bellamy | City Winery - Boston
Boston, MA | Friday
4/17/2026
7:30 PM | |
| Paloma Diamond | City Winery - Boston
Boston, MA | Sunday
4/19/2026
7:30 PM | |
| Chris Smither | City Winery - Boston
Boston, MA | Wednesday
4/22/2026
7:30 PM | |
| Lee Ritenour | City Winery - Boston
Boston, MA | Thursday
4/23/2026
7:30 PM | |
| Emma Grede | City Winery - Boston
Boston, MA | Friday
4/24/2026
7:30 PM | |
| The Neon Queen: Mamma Mia Brunch | City Winery - Boston
Boston, MA | Sunday
4/26/2026
12:00 PM | |
| Matthew & Gunnar Nelson | City Winery - Boston
Boston, MA | Sunday
4/26/2026
7:30 PM | |
| Zuhal Olcay | City Winery - Boston
Boston, MA | Tuesday
4/28/2026
7:30 PM | |
| Will Downing | City Winery - Boston
Boston, MA | Friday
5/1/2026
7:30 PM | |
| Steam Powered Giraffe | City Winery - Boston
Boston, MA | Sunday
5/3/2026
7:30 PM | |
| Melissa Manchester | City Winery - Boston
Boston, MA | Monday
5/4/2026
7:30 PM | |
| The Messthetics & James Brandon Lewis | City Winery - Boston
Boston, MA | Tuesday
5/5/2026
7:30 PM | |
| Rey Royale | City Winery - Boston
Boston, MA | Sunday
5/10/2026
12:00 PM | |
| Sonja Morgan | City Winery - Boston
Boston, MA | Monday
5/11/2026
7:30 PM | |
| Vanessa Carlton | City Winery - Boston
Boston, MA | Tuesday
5/12/2026
7:30 PM | |
| Vanessa Carlton | City Winery - Boston
Boston, MA | Wednesday
5/13/2026
7:30 PM | |
| Lotus Land - A Tribute to Rush | City Winery - Boston
Boston, MA | Saturday
5/16/2026
7:30 PM | |
| Clint Black - In Conversation | City Winery - Boston
Boston, MA | Thursday
5/21/2026
7:30 PM | |
| Challenge Mania Live | City Winery - Boston
Boston, MA | Friday
5/22/2026
7:00 PM | |
| Challenge Mania Live: The Roast of Cara Maria | City Winery - Boston
Boston, MA | Saturday
5/23/2026
7:00 PM | |
| Stephen Lynch | City Winery - Boston
Boston, MA | Wednesday
6/3/2026
7:30 PM | |
| T. Murph | City Winery - Boston
Boston, MA | Sunday
6/7/2026
7:30 PM | |
| Alejandro Aranda | City Winery - Boston
Boston, MA | Monday
6/8/2026
7:30 PM | |
| Davide De Pierro | City Winery - Boston
Boston, MA | Friday
6/19/2026
7:30 PM | |
| Catieosaurus: Wildly Unprepared | City Winery - Boston
Boston, MA | Sunday
6/28/2026
7:30 PM | |
| Lyle Lovett | City Winery - Boston
Boston, MA | Monday
6/29/2026
7:30 PM | |
| Lyle Lovett | City Winery - Boston
Boston, MA | Tuesday
6/30/2026
7:30 PM | |
| Lyle Lovett | City Winery - Boston
Boston, MA | Wednesday
7/1/2026
7:30 PM | |
| The Christi Show | City Winery - Boston
Boston, MA | Thursday
7/2/2026
7:30 PM | |
| Babatunde HipHopera | City Winery - Boston
Boston, MA | Sunday
7/5/2026
7:30 PM | |
| Stewart Copeland | City Winery - Boston
Boston, MA | Thursday
7/9/2026
7:30 PM | |
| D.L. Hughley | City Winery - Boston
Boston, MA | Friday
7/24/2026
6:00 PM | |
| D.L. Hughley | City Winery - Boston
Boston, MA | Friday
7/24/2026
9:30 PM | |
| D.L. Hughley | City Winery - Boston
Boston, MA | Saturday
7/25/2026
6:00 PM | |
| D.L. Hughley | City Winery - Boston
Boston, MA | Saturday
7/25/2026
9:30 PM | |
| D.L. Hughley | City Winery - Boston
Boston, MA | Sunday
7/26/2026
5:00 PM | |
| The Surfaris | City Winery - Boston
Boston, MA | Thursday
7/30/2026
7:30 PM | |
| AJ Ghent | City Winery - Boston
Boston, MA | Sunday
8/9/2026
7:30 PM | |
| Lyfe Jennings | City Winery - Boston
Boston, MA | Saturday
8/15/2026
6:30 PM | |
| Lyfe Jennings | City Winery - Boston
Boston, MA | Saturday
8/15/2026
9:30 PM | |
| Southern Culture On The Skids | City Winery - Boston
Boston, MA | Tuesday
9/29/2026
6:30 PM | |
| Steam Powered Giraffe | City Winery - Boston
Boston, MA | Wednesday
9/30/2026
7:30 PM | |
| Damn The Torpedoes - Tom Petty Tribute | City Winery - Boston
Boston, MA | Sunday
10/4/2026
7:30 PM | |
| Yasmin Williams | City Winery - Boston
Boston, MA | Sunday
10/18/2026
7:30 PM | |
