May 1 | May 1 | We Are Family | Henry’s Music Hall | 9:30pm-12:30am | R&B/Pop |
| May 1 | Suffering Moses | Henry’s Stage | 9:30pm-12:30am | Blues/Rock |
May 2 | May 2 | Bubba & Dale | Patio | 2-5pm | Country |
| May 2 | Henry Gates | Anson Lounge | 2-5pm | Acoustic Covers |
| May 2 | Zach Quillen | Anson Lounge | 7-10pm | Blues/Rock |
| May 2 | Coley Williams Band | Henry’s Music Hall | 10pm-1am | Country |
| May 2 | Gator Food | Whiskey Room | 10pm-1am | Alternative |
| May 2 | BenderFunk | Henry’s Stage | 10pm-1am | Rock |
May 3 | May 3 | Dylan Andrews | Patio | 2-5pm | Country, Acoustic Covers |
| May 3 | Henry Gates | Anson Lounge | 2-5pm | Acoustic Covers |
| May 3 | Loren Griste | Anson Lounge | 7-10pm | Country/Top 40 |
| May 3 | Tidal Jive | Henry’s Music Hall | 10pm-1am | Rock/Pop |
| May 3 | Chris Williams | Whiskey Room | 10pm-1am | R&B/Jazz |
| May 3 | Purple Magnolia | Henry’s Stage | 10pm-1am | Country/Top 40 |
May 4 | May 4 | Chris Roberts | Patio | 2-5pm | Soul/Blues |
| May 4 | Gracious Day | Henry’s Stage | 9:30pm-12:30am | Acoustic Country |
May 5 | May 5 | Market Street Cowboy Band | Henry’s Stage | 9:30pm-12:30am | Country/Top 40 |
May 6 | May 6 | Chris Williams | Henry’s Stage | 10pm-1am | R&B/Jazz |
May 7 | May 7 | Gracious Day | Henry’s Stage | 9:30pm-12:30am | Acoustic Country |
May 8 | May 8 | Vynl Countdown | Henry’s Music Hall | 10pm-1am | Top 40 |
| May 8 | Suffering Moses | Henry’s Stage | 10pm-1am | Blues/Rock |
May 9 | May 9 | Bubba & Dale | Patio | 2-5pm | Country/Top 40 |
| May 9 | Molly Durnin | Anson Lounge | 2-5pm | Folk/Alternative Rock |
| May 9 | Zach Quillen | Anson Lounge | 7-10pm | Blues/Rock |
| May 9 | Vynl Countdown | Henry’s Music Hall | 10pm-1am | Top 40 |
| May 9 | Joe Wheaton | Whiskey Room | 10pm-1am | Acoustic Blues/Rock |
| May 9 | Tidal Jive | Henry’s Stage | 10pm-1am | R&B/Pop |
May 10 | May 10 | Joe Fisher | Patio | 2-5pm | Acoustic Rock |
| May 10 | Lola Grace | Anson Lounge | 2-5pm | Folk/Country |
| May 10 | Vynl Countdown | Henry’s Music Hall | 10pm-1am | Top 40 |
| May 10 | Chris Williams | Whiskey Room | 10pm-1am | R&B/Jazz |
| May 10 | Keidre Band | Henry’s Stage | 10pm-1am | Classics |
May 11 | May 11 | Spud Fisher | Patio | 2-5pm | Country |
| May 11 | Gracious Day | Henry’s Stage | 9:30pm-12:30am | Acoustic Country |
May 12 | May 12 | Market Street Cowboy Band | Henry’s Stage | 9:30pm-12:30am | Country/Top 40 |
May 13 | May 13 | Chris Williams | Henry’s Stage | 10-1pm | R&B/Jazz |
May 14 | May 14 | Gracious Day | Henry’s Stage | 9:30-12:30pm | Acoustic Country |
May 15 | May 15 | We Are Family | Henry’s Music Hall | 10pm-1am | R&B/Pop |
| May 15 | Suffering Moses | Henry’s Stage | 10pm-1am | Blues/Rock |
May 16 | May 16 | Bubba & Dale | Patio | 2-5pm | Country/Top 40 |
| May 16 | Molly Durnin | Anson Lounge | 2-5pm | Folk/Alternative Rock |
| May 16 | Zach Quillen | Anson Lounge | 7-10pm | Blues/Rock |
| May 16 | Deadbeat Club | Henry’s Music Hall | 10pm-1am | Classic Rock |
| May 16 | Me & Mr. Jones | Whiskey Room | 10pm-1am | R&B |
| May 16 | Poke the Bear | Henry’s Stage | 10pm-1am | Top 40 |
May 17 | May 17 | Spoda | Patio | 2-5pm | Alternative |
| May 17 | Loren Griste | Anson Lounge | 2-5pm | Country/Top 40 |
| May 17 | Dirt Road Disciples | Music Hall | 10pm-1am | Country/Rock |
| May 17 | Chris Williams | Whiskey Room | 10pm-1am | R&B/Jazz |
| May 17 | BenderFunk | Henry’s Stage | 10pm-1am | Rock |
May 18 | May 18 | Macelyn Batten | Patio | 2-5pm | Country Classics |
| May 18 | Gracious Day | Henry’s Stage | 9:30pm-12:30am | Acoustic Country |
May 19 | May 19 | Market Street Cowboy Band | Henry’s Stage | 9:30pm-12:30am | Country/Top 40 |
May 20 | May 20 | Chris Williams | Henry’s Stage | 10-1pm | R&B/Jazz |
May 21 | May 21 | Gracious Day | Henry’s Stage | 9:30pm-12:30am | Acoustic Country |
May 22 | May 22 | Market Street Cowboy Band | Henry’s Music Hall | 10pm-1am | Country/Top 40 |
| May 22 | Suffering Moses | Henry’s Stage | 10pm-1am | Blues/Rock |
May 23 | May 23 | Bubba & Dale | Patio | 2-5pm | Country/Top 40 |
| May 23 | Gracious Day | Anson Lounge | 2-5pm | Acoustic Country |
| May 23 | Zach Quillen | Anson Lounge | 7-10pm | Blues/Rock |
| May 23 | Market Street Cowboy Band | Henry’s Music Hall | 10pm-1am | Country/Top 40 |
| May 23 | Gator Food | Whiskey Room | 10pm-1am | Alternative |
| May 23 | Keidre Band | Henry’s Stage | 10pm-1am | Classics |
May 24 | May 24 | Nathan Davis | Patio | 2-5pm | Alternative |
| May 24 | Molly Durnin | Anson Lounge | 2-5pm | Folk/Alternative Rock |
| May 24 | Market Street Cowboy Band | Henry’s Music Hall | 10pm-1am | Country/Top 40 |
| May 24 | Chris Williams | Whiskey Room | 10pm-1am | R&B/Jazz |
| May 24 | Fuze Box | Henry’s Stage | 10pm-1am | Rock/Top 40 |
May 25 | May 25 | Joe | Fisher | 2-5pm | Acoustic Rock |
| May 25 | Tidal Jive | Henry’s Music Hall | 10pm-1am | Rock/Pop |
| May 25 | Gracious Day | Henry’s Stage | 10pm-1am | Acoustic Country |
May 26 | May 26 | Jack Triebold | Patio | 2-5pm | - |
| May 26 | Market Street Cowboy | Band | 9:30pm-12:30am | Country/Top 40 |
May 27 | May 27 | Chris Williams | Henry’s Stage | 10-1pm | R&B/Jazz |
May 28 | May 28 | Gracious Day | Henry’s Stage | 9:30pm-12:30am | Acoustic Country |
May 29 | May 29 | Chief Brody | Henry’s Music Hall | 10pm-1am | Top 40/Rock |
| May 29 | Suffering Moses | Henry’s Stage | 10pm-1am | Blues/Rock |
May 30 | May 30 | Bubba & Dale | Patio | 2-5pm | Country/Top 40 |
| May 30 | Molly Durnin | Anson Lounge | 2-5pm | Folk/Alternative Rock |
| May 30 | Zach Quillen | Anson Lounge | 7-10pm | Blues/Rock |
| May 30 | Chief Brody | Henry’s Music Hall | 10pm-1am | Top 40/Rock |
| May 30 | Joe Wheaton | Whiskey Room | 10pm-1am | Acoustic Blues/Rock |
| May 30 | Tidal Jive | Henry’s Stage | 10pm-1am | Rock/Pop |
May 31 | May 31 | Molly Durnin | Patio | 2-5pm | Folk/Alternative Rock |
| May 31 | Loren Griste | Anson Lounge | 7-10pm | Country/Top 40 |
| May 31 | Chief Brody | Henry’s Music Hall | 10pm-1am | Top 40/Rock |
| May 31 | Chris Williams | Whiskey Room | 10pm-1am | R&B/Jazz |
| May 31 | Tidal Jive | Henry’s Stage | 10pm-1am | Rock/Pop |