June 1 | June 1 | Loren Griste | Patio | 2pm-5pm | Country/Top 40 |
| June 1 | Gracious Day | Henry’s Stage | 9:30pm-12:30am | Acoustic Country |
June 2 | June 2 | Market Street Cowboy Band | Henry’s Stage | 9:30pm-12:30am | Country/Top 40 |
June 3 | June 3 | Chris Williams | Henry’s Stage | 10pm-1am | Jazz/R&B |
June 4 | June 4 | Gracious Day | Henry’s Stage | 9:30pm-12:30am | Acoustic Country/Classics |
June 5 | June 5 | Sunny & The Honey | Henry’s Music Hall | 10pm-1am | Rock/Pop |
| June 5 | Suffering Moses | Henry’s Stage | 10pm-1am | Blues/Rock |
June 6 | June 6 | Bubba & Dale | Patio | 2-5pm | Country |
| June 6 | Jack Triebold | Anson Lounge | 2-5pm | Acoustic Guitarist |
| June 6 | Zach Quillen | Anson Lounge | 7-10pm | Rock/Blues |
| June 6 | Sunny & The Honey | Henry’s Music Hall | 10pm-1am | Rock/Pop |
| June 6 | Bubba & Dale | Whiskey Room | 10pm-1am | Country/Top 40 |
| June 6 | Kellie’s Playhouse | Henry’s Stage | 10pm-1am | Rock/Classics |
June 7 | June 7 | Spoda | Patio | 2-5pm | Indie/Rock |
| June 7 | Macelyn Batten | Anson Lounge | 2-5pm | Country/Classics |
| June 7 | Jon Hanks | Anson Lounge | 7-10pm | Country |
| June 7 | We Are Family | Henry’s Music Hall | 10pm-1am | R&B/Pop |
| June 7 | Chris Williams | Whiskey Room | 10pm-1am | Jazz/Pop |
| June 7 | Gator Food | Henry’s Stage | 10pm-1am | Alternative/Rock |
June 8 | June 8 | Joe Fisher | Patio | 2pm-5pm | Acoustic Rock |
| June 8 | Gracious Day | Henry’s Stage | 9:30pm-12:30am | Acoustic Country/Classics |
June 9 | June 9 | Market Street Cowboy Band | Henry’s Stage | 9:30pm-12:30am | Country/Top 40 |
June 10 | June 10 | Chris Williams | Henry’s Stage | 10pm-1am | Jazz/R&B |
June 11 | June 11 | Gracious Day | Henry’s Stage | 9:30pm-12:30am | Acoustic Country/Classics |
June 12 | June 12 | We Are Family | Henry’s Music Hall | 10pm-1am | R&B/Pop |
| June 12 | Suffering Moses | Henry’s Stage | 10pm-1am | Rock/Blues |
June 13 | June 13 | Bubba & Dale | Patio | 2-5pm | Country |
| June 13 | Jack Triebold | Anson Lounge | 2-5pm | Acoustic Guitarist |
| June 13 | Zach Quillen | Anson Lounge | 7-10pm | Rock/Blues |
| June 13 | Soulfish | Henry’s Music Hall | 10pm-1am | Classics/Pop |
| June 13 | Bubba & Dale | Whiskey Room | 10pm-1am | Country/Top 40 |
| June 13 | Keidre Band | Henry’s Stage | 10pm-1am | Classics/Oldies |
June 14 | June 14 | Molly Durnin | Patio | 2-5pm | Alternative Rock/Folk |
| June 14 | Macelyn Batten | Anson Lounge | 2-5pm | Country/Classics |
| June 14 | Joe Wheaton | Anson Lounge | 7-10 | Folk |
| June 14 | Deadbeat Club | Henry’s Music Hall | 10pm-1am | Soft Rock/Top 40 |
| June 14 | Chris Williams | Whiskey Room | 10pm-1am | Jazz/R&B |
| June 14 | We Are Family | Henry’s Stage | 10pm-1am | R&B/Pop |
June 15 | June 15 | Chris Roberts | Patio | 2pm-5pm | Folk |
| June 15 | Gracious Day | Henry’s Stage | 9:30pm-12:30am | Acoustic Country |
June 16 | June 16 | Market Street Cowboy Band | Henry’s Stage | 9:30pm-12:30am | Country/Top 40 |
June 17 | June 17 | Chris Williams | Henry’s Stage | 10pm-1am | Jazz/R&B |
June 18 | June 18 | Gracious Day | Henry’s Stage | 9:30pm-12:30am | Acoustic Country |
June 19 | June 19 | Market Street Cowboy Band | Henry’s Music Hall | 10pm-1am | Country/Top 40 |
| June 19 | Suffering Moses | Henry’s Stage | 10pm-1am | Rock/Blues |
June 20 | June 20 | Bubba & Dale | Patio | 2-5pm | Country |
| June 20 | Molly Durnin | Anson Lounge | 2-5pm | Alternative Rock/Folk |
| June 20 | Zach Quillen | Anson Lounge | 7-10pm | Rock/Blues |
| June 20 | Market Street Cowboy Band | Henry’s Music Hall | 10pm-1am | Country/Top 40 |
| June 20 | Kellie’s Playhouse | Whiskey Room | 10pm-1am | Rock/Classics |
| June 20 | Keidre Band | Henry’s Stage | 10pm-1am | Classics/Oldies |
June 21 | June 21 | Joe Fisher | Patio | 2-5pm | Acoustic Rock |
| June 21 | Macelyn Batten | Anson Lounge | 2-5pm | Country/Oldies |
| June 21 | Jon Hanks | Anson Lounge | 7-10pm | Country |
| June 21 | Market Street Cowboy Band | Henry’s Music Hall | 10pm-1am | Country/Top 40 |
| June 21 | Chris Williams | Whiskey Room | 10pm-1am | R&B/Jazz |
| June 21 | Token Mary | Henry’s Stage | 10pm-1am | Classic Covers/Pop |
June 22 | June 22 | Spud Fisher | Patio | 2pm-5pm | Country/Folk |
| June 22 | Gracious Day | Henry’s Stage | 9:30pm-12:30am | Acoustic Country |
June 23 | June 23 | Market Street Cowboy Band | Henry’s Stage | 9:30pm-12:30am | Country/Top 40 |
June 24 | June 24 | Chris Williams | Henry’s Stage | 10pm-1am | Jazz/R&B |
June 25 | June 25 | Gracious Day | Henry’s Stage | 9:30pm-12:30am | Acoustic Country |
June 26 | June 26 | Token Mary | Henry’s Music Hall | 10pm-1am | Pop/Classics |
| June 26 | Suffering Moses | Henry’s Stage | 10pm-1am | Rock/Blues |
June 27 | June 27 | Bubba & Dale | Patio | 2-5pm | Country |
| June 27 | Gracious Day | Anson Lounge | 2-5pm | Acoustic Country |
| June 27 | Zach Quillen | Anson Lounge | 7-10pm | Rock/Blues |
| June 27 | Sill Crow | Henry’s Music Hall | 10pm-1am | Folk/Rock |
| June 27 | Bubba & Dale | Whiskey Room | 10pm-1am | Country |
| June 27 | Sunny & The Honey | Henry’s Stage | 10pm-1am | Rock/Pop |
June 28 | June 28 | Spoda | Patio | 2-5pm | Indie/Rock |
| June 28 | Molly Durnin | Anson Lounge | 2-5pm | Alternative Rock/Folk |
| June 28 | Kelly Sanchez | Anson Lounge | 7-10pm | Folk/Soft Rock |
| June 28 | Take the Lead | Henry’s Music Hall | 10pm-1am | Classic Rock/Early 2000’s |
| June 28 | Chris Williams | Whiskey Room | 10pm-1am | R&B/Jazz |
| June 28 | Sunny & The Honey | Henry’s Stage | 10pm-1am | Rock/Pop |
June 29 | June 29 | Brandon Simmons | Patio | 1pm-4pm | Classics/Pop |
| June 29 | Gracious Day | Henry’s Stage | 9:30pm-12:30am | Acoustic Country |
June 30 | June 30 | Market Street Cowboy Band | Henry’s Stage | 9:30pm-12:30am | Country/Top 40 |