| 1995 | 1996 | 1997 | 1998 | ||||
|---|---|---|---|---|---|---|---|
| folk duo | Atwater Donnelly | bluegrass | Old Cold Tater | bluegrass | Northern Lights | afro-pop | Wildest Dreams |
| brass | Epic Brass | singer | Brooks Williams | country | John Lincoln Wright | ||
| Peruvian | Inca Son | Cajun | Boogaloo Swamis | Irish folk | Cathie Ryan | ||
| classical | Vox One | western swing | Western Omlette | blues | Boston Baked Blues | ||
| afro-pop | Wildest Dreams | military band | USAF Band of Liberty | ||||
| blues | Megawatt Blues Crushers | New Orleans | Hot Tamale Brass Band | ||||
| big band | Something Cool | Latin folk | Sol y Canto | ||||
| Celtic folk | Woods Tea Co. | bluegrass | Northern Lights | ||||
| 1999 | 2000 | 2001 | 2002 | ||||
| Peruvian folk | Inca Son | pops | Air Force Band of Liberty | Beatles | Beatlejuice | a capella | Five O’Clock Shadow |
| Cajun | Boogaloo Swamis | African | Mamadou Diop | klezmer | Klezperanto | fiddle/rock | Drowsey Maggie |
| blues | Megawatt Blues Crushers | blues | Troy Gonyea | swing | Swing Legacy | swing | Happy Feet Orchestra |
| bluegrass | Northern Lights | Native American | Bill Miller | American roots | Tarbox Ramblers | Gypsy | Kakalla |
| gospel | Evelyn McDonald | folk duo | Atwater Donnelly | brass quintet | Innovata Brass | bbq rock | Trailer Park |
| Beatles | Beatle Juice | Acadian folk | Chanterelle | folk/rock | Jake Armerding | ||
| brass | Quintessential Brass | folk rock | Jake Amerding | Acadian folk | Chanterelle | ||
| gospel | Evelyn McDonald | blues | Blues Bros cover | folk duo | Atwater-Donnelly | ||
| 2003 | 2004 | 2005 | 2006 | ||||
| reggae | Dub Station | fiddle/rock | Crazy Maggie | Celtic rock | The Kissers | blugrass/jazz | Jaded Mand/Pent Jazz |
| rock | Drowzy Maggie | Polka | East Side Groove | alt country | Cigar Store Indians | Celtic rock | The Kissers |
| Dixieland | Ancient Mariners | Dixieland | Ancient Mariners | Cajun | Boogaloo Swamis | sing /song | Sarah Borgess |
| fiddler | Joyce Anderson | fiddle/folk | Joyce Anderson | sing/song | Carla Ryder Band | blues/rock | Megawatt Blues Crushers |
| Cajun rock | Cake Walk | Celtic rock | Johnny Come Latelies | Neil Young | Rust Never Sleeps | cover rock | Sofa Kings |
| sing/song | Carla Ryder | Neil Young | Rust Never Sleeps | country | Almost Cowboyz | Celtic rock | Down Dog |
| pop trio | Maeve | bbq rock | Trailer Park | western swing | Bagboys | cover rock/pop | Rte 97 North |
| bbq rock | Trailer Park | eclectic | Rani Arbo and daisy mayhem | Latin | Grupo Fantasia | rock | Averi |
| 2007 | 2008 | 2009 | 2010 | ||||
| Latin | Grupo Fantasia | rock, R&B | Orville Giddings | brass quintet | Quintessential Brass | neo-soul/ retro R&B | Soul Alley |
| R&B | Sweet Willie D | Neil Young | Rust Never Sleeps | bluegrass | Hot Day at the Zoo | Roots, rock & blues | Porch Rockers |
| folk | Goodhues | cover rock | Don't Call Me Shirley | tween rock | Michael & Marisa | Contemporary & original R&R | Under Atoms |
| soul | Soul Ambition | opera | Darby Tench is Opera! | blues | Alley Blues | 60s–70s pop/soul | Jenny Dee & the Deelinquents |
| pop/ rock | Chad Perrone | Beatles | Rte 97 North | R&B, soul | Jesse Dee | Americana | Girls Guns & Glory |
| contest | Battle of the Bands | Delta Blues | Erin Harpe | ||||
| 60s–70s pop/soul | Don’t Call Me Shirley | ||||||
| 2011 | |||||||
| Woman-fronted Blues | The Dirty Mac Blues Band |
| Roots, rock quartet | Porch Rockers |
| Delta Blues | Erin Harpe |
| Folk/Rock | The Goodhues Band |
| Credence Clearwater Revival cover band | Bad Moon Rising |
| 80s–90s rock | Five O’Clock Somewhere |