| Date | Time | Name |
|---|
| Fri Sep 11 | 6:00p | Mark Riley Project - Summer Music at the O' |
| Thu Sep 10 | 7:00p | Line Dancing |
| Fri Sep 4 | 6:00p | Jamie Alcorn Band - Summer Music at the O' |
| Thu Sep 3 | 7:00p | Line Dancing |
| Fri Aug 28 | 6:00p | The Rhinestone Romeos - Summer Music at the O' |
| Thu Aug 27 | 7:00p | Line Dancing |
| Fri Aug 21 | 6:00p | Joker's Right - Summer Music at the O' |
| Thu Aug 20 | 7:00p | Line Dancing |
| Fri Aug 14 | 6:00p | The Hupman Brothers Band - Summer Music at the O' |
| Thu Aug 13 | 7:00p | Line Dancing |
| Fri Aug 7 | 6:00p | Shrimp Daddy & The Sharp Shooters - Summer Music at the O' |
| Thu Aug 6 | 7:00p | Line Dancing |
| Mon Aug 3 | 6:00p | Joker's Right - Summer Music at the O' |
| Fri Jul 31 | 6:00p | The Soul Tides - Summer Music at the O' |
| Thu Jul 30 | 7:00p | Line Dancing |
| Fri Jul 24 | 6:00p | The Kim Doolittle Band - Summer Music at the O' |
| Thu Jul 23 | 7:00p | Line Dancing |
| Fri Jul 17 | 6:00p | The Big Sound Small Band - Summer Music at the O' |
| Thu Jul 16 | 7:00p | Line Dancing |
| Fri Jul 10 | 6:00p | The Rhinestone Romeos - Summer Music at the O' |
| Thu Jul 9 | 7:00p | Line Dancing |
| Fri Jul 3 | 6:00p | The Hupman Brothers Band - Summer Music at the O' |
| Thu Jul 2 | 7:00p | Line Dancing |
| Fri Jun 26 | 6:00p | B.C. & Burning Love - Summer Music at the O' |
| Thu Jun 25 | 7:00p | Line Dance The Rhinestone Romeos |
| Fri Jun 19 | 6:00p | One Night Only - Summer Music at the O' |
| Thu Jun 18 | 7:00p | Line Dancing |
| Fri Jun 12 | 6:00p | Ruth Manning & The Prospectors - Summer Music at the O' |
| Thu Jun 11 | 7:00p | Line Dancing |
| Sep 1, 2024 | 6:00p | Gospel Concert |
| Sep 22, 2023 | 6:00p | The Miss Aurora Scott Quartet |
| Sep 15, 2023 | 6:00p | The Rhinestones Romeos |
| Sep 8, 2023 | 6:00p | The Mark Riley Project |
| Sep 1, 2023 | 6:00p | Joker's Right |
| Aug 25, 2023 | 6:00p | Kim Doolittle & Band |
| Aug 18, 2023 | 6:00p | The Slow Burn Blues Band |
| Aug 11, 2023 | 6:00p | The Sundries |
| Aug 5, 2023 | 6:00p | Ruth Manning & the Prospectors |
| Jul 28, 2023 | 6:00p | The Hupman Brothers Band |
| Jul 21, 2023 | 6:00p | The Sundries |
| Jul 14, 2023 | 6:00p | Mark Bezanson Band |
| Jul 7, 2023 | 6:00p | The Rhinestone Romeos |
| Jun 30, 2023 | 6:00p | Joker's Right |
| Sep 16, 2022 | 6:00p | Summer Concert Series |
| Sep 9, 2022 | 6:00p | Summer Concert Series |
| Sep 2, 2022 | 6:00p | Summer Concert Series |
| Aug 26, 2022 | 6:00p | Summer Concert Series |
| Aug 19, 2022 | 6:00p | Summer Concert Series |
| Aug 12, 2022 | 6:00p | Summer Concert Series |
| Aug 5, 2022 | 6:00p | Summer Concert Series |
| Jul 31, 2022 | 7:30p | Steph Peaks Drag Performance |
| Jul 30, 2022 | 6:00p | Summer Concert Series |
| Jul 30, 2022 | 2:00p | Annapolis Skippers Performance |
| Jul 22, 2022 | 6:00p | Summer Concert Series |
| Jul 15, 2022 | 6:00p | Summer Concert Series |
| Jul 9, 2022 | 9:00a | Pride Day |
| Jul 8, 2022 | 6:00p | Summer Concert Series |
| Jul 3, 2022 | 3:00p | Fundraising Benefit for Ukraine LGBTQ+ NGOs |
| Aug 7, 2021 | 5:30p | Country Music Weekend- The Rhinestone Romeos |
| Aug 6, 2021 | 6:00p | Summer Concert Series- The Sundries |
| Aug 1, 2021 | 6:30p | Natal Day- Callehan |
| Aug 1, 2021 | 2:00p | Natal Day- Sarah Pound & John Ebata |
| Jul 31, 2021 | 1:00p | Kids Event and Annapolis' Got Talent |
| Jul 30, 2021 | 7:00p | Natal Day- Tide and Timbre |
| Jul 30, 2021 | 4:00p | Natal Day- Tap Room Growlers |
| Jul 23, 2021 | 6:00p | Summer Concert Series |
| Aug 28, 2020 | 6:00p | Rhinestone Romeos |
| Aug 21, 2020 | 6:00p | Electric Vegas |
| Aug 14, 2020 | 6:00p | The Dogs of Summer at the O |
| Aug 7, 2020 | 6:00p | The Clamdiggers |
| Jul 31, 2020 | 6:00p | Hupman Brothers Band |
| Jul 24, 2020 | 6:00p | Mark Bezanson Trio |
| Jul 17, 2020 | 6:00p | Whisky Creek at the O |
| Aug 30, 2019 | 6:00p | Annapolis Community Band |
| Aug 24, 2019 | 1:00p | Theresa Porter |
| Aug 23, 2019 | 6:00p | Brian Wambolt |
| Aug 16, 2019 | 6:00p | Idle Threats |
| Aug 9, 2019 | 6:00p | Lost Vegas |
| Aug 3, 2019 | 2:00p | HMCS Acadia Sea Cadets |
| Aug 3, 2019 | 11:00a | Natural Art Festival |
| Jul 27, 2019 | 1:00p | Bob Marshall |
| Jul 26, 2019 | 6:00p | Joker's Right |
| Jul 20, 2019 | 1:00p | HMCS Acadia Senior Band |
| Jul 19, 2019 | 6:00p | Clamdiggers |
| Jul 13, 2019 | 1:00p | Caroline Bosley |
| Jul 12, 2019 | 6:00p | Justin Wood |
| Jul 6, 2019 | 7:00p | John Muirhead |
| Jul 5, 2019 | 6:00p | Kings of Obscurity |
| Jun 7, 2019 | 5:30p | Barbecue & Music Fundraiser |
| Aug 18, 2018 | 1:00p | Michael Robertson |
| Aug 17, 2018 | 6:00p | Ida Red |
| Aug 10, 2018 | 6:00p | Justin Wood |
| Jul 28, 2018 | 1:00p | HMC Acadia Cadets |
| Jul 27, 2018 | 6:00p | Zakary & The Valley Vipers |
| Jul 27, 2018 | 3:00p | Textopia |
| Jul 21, 2018 | 1:00p | Theresa Porter |
| Jul 20, 2018 | 6:00p | Rhythm Rogues |
| Jul 20, 2018 | 1:00p | The Lorax |
| Jul 14, 2018 | 1:00p | HMC Acadia Cadets |
| Jul 13, 2018 | 6:00p | Phil DeMille & Hourglass |
| Jul 7, 2018 | 1:00p | Bob Marshall |
| Jul 6, 2018 | 6:00p | Idle Threats |
| Jul 1, 2018 | 2:00p | Shakespeare by the Shore |
| Jul 1, 2018 | 10:30a | Shakespeare by the Shore |
| Jun 24, 2018 | 8:30a | Walk, Run, Ride Don't Hide |
| Jun 2, 2018 | 1:00p | James Gordon |
| Jun 1, 2018 | 6:00p | Duncan J.Draper, Gregg Mazel, Taren Yelle play Jazz |
| Jun 30, 2017 | 2:00p | Music |
