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- 07/19/2009 - Jesse Pilgrim Video Shoot
- 07/21/2009 - CANCELED: Deer Tick, Dawes, Dead End Armory
- 07/23/2009 - Samuel James and D. Gross
- 07/24/2009 - Jesse Pilgrim with Over a Cardboard Sea
- 07/25/2009 - Jesse Pilgrim Video Release
- 07/30/2009 - Seymour, Wand, South China and Fire on Fire $7
- 07/31/2009 - Clues (formerly The Unicorns), Goes Cube and Marie Stella
- 08/01/2009 - Wesley Hartley, Cursillistas
- 08/05/2009 - *HillyTown Presents: Boxy, Theodore Treehouse, and Haru Bangs
- 08/07/2009 - Jesse Pilgrim and Marie Moreshead
- 08/12/2009 - *HillyTown Presents: Panda Bandits, Dan Wholey, and Jesse Pilgrim
- 08/14/2009 - Brown Bird, Dead End Armory and Chriss Sutherland
- 08/19/2009 - *HillyTown Presents: Phantom Computers, Happy Machines, and Dead End Armory
- 08/21/2009 - Dead End Armory
- 08/22/2009 - Sam James Cd Release Party
- 08/26/2009 - *HillyTown Presents: White Light, Blood Warrior, and Mark Summers
- 08/28/2009 - Jesse Pilgrim, Dead End Armory and Jennifer Matthews
- 08/29/2009 - Ray Lamontagne and Rustic Overtones
- 09/01/2009 - Roomful of Guns/ Johnsons Crossroad (Moses Atwood)
- 09/10/2009 - Deerhunter
- 09/10/2009 - The Government Pop Issue 2, Dead End Armory, Tica Douglas
- 09/12/2009 - Spencer & The School Spirit Mafia Beatles Tribute
- 09/18/2009 - Anna's Ghost CD Release Party, Dead Man's Clothes and Jesse Pilgrim
- 09/19/2009 - Eric Bettencourt CD Release Show, Jacob Augustine
- 09/19/2009 - Hillytown Episode 2 Released @ Midnight
- 09/20/2009 - Chain And The Gang, BOXY, Panda Bandits, BAM BAM
- 09/25/2009 - Run On Sentence, Computer At Sea, Renee Arozqueta
- 09/29/2009 - Screaming Females, Marie Stella, Rattlesnakes
- 09/30/2009 - Wes Hartley and The Splitting Logs
- 10/02/2009 - Jennifer Matthews, Jesse Pilgrim, and Dead End Armory
- 10/03/2009 - Sufjan Stevens, Cryptacize
- 10/03/2009 - Big Bang TV, Dead End Armory, and Isobell
- 10/15/2009 - Wesley Allen Hartley and the Splitting Logs, Barn Burning, and Billy Wallace
- 10/17/2009 - HELL NO ON ONE
- 10/18/2009 - HELL NO ON ONE ALL AGES
- 10/23/2009 - Blood Warrior, Honeydew Drops, and Jesse Pilgrim
- 10/24/2009 - Andrew Bird and St. Vincent
- 11/02/2009 - Pete Yorn and Alberta Cross
- 11/10/2009 - Brother Ali
- 11/18/2009 - Minus The Bear
- 11/21/2009 - NEEDTOBREATHE, Jacob Augustine, and Marie Moreshead
- 12/04/2009 - Brown Bird CD RELEASE (MAINE), The Honey Clouds, The Plains
- 12/05/2009 - Benjamin Burgess Cd release weekend - Adam and The Waxmen, Dominic and The Lucid, Christian Cuff, and Darell Foster
- 12/06/2009 - Benjamin Burgess CD release weekend - Lady Lamb The Beekeeper, Eric Bettencourt, Jesse Pilgrim and Special Guests
- 12/12/2009 - [dog]and[pony] dvd release show! Jacob Augustine + Lady Lamb The Beekeeper, Wes Hartley + Chriss Sutherland, Marie Stella + Kris Rodgers, Jesse Pilgrim + D. Gross, Sam James, and The Loblolly Boy
- 12/18/2009 - Olas! flamenco music featuring Chriss Sutherland
- 12/20/2009 - Wesley Allen Hartley & The Traveling Trees and Sore Eros
- 12/20/2009 - Planets Around The Sun, Tempera, Prisma, Hersey State, Tin Ceilings, Computer At Sea, Crank Sturgeon
- 12/26/2009 - Ladies Night: Sara Halle Richardson, Lady Lamb The Beekeeper and Courtney Underwood
- 12/26/2009 - Wesley Allen Hartley and The Traveling Trees And the No. 9
- 01/08/2010 - Kino Proby
- 01/15/2010 - Emily Hope Price (NY) and Lady Lamb The Beekeeper
- 01/22/2010 - Metal Feathers, Spouse, and Parlour Steps
- 01/23/2010 - Roy Davis, Dave Gutter + Evan Casas, and Marie Moreshead
- 01/29/2010 - Eternal Otter Records Party!!! Aly Spaltro, TJ Metcalfe, Blaque Boose, Panda Bandits, Dana Gross, Jesse Pilgrim, and Over A Cardboard Sea
- 01/29/2010 - Ben Burgess
- 02/01/2010 - Prince Rama, Peace, Loving, Planets Around the Sun, and Theodore Treehouse
- 02/02/2010 - Lady Lamb The Beekeeper and Dilly Dilly
- 02/04/2010 - Jakob Battick and Friends, Planets Around the Sun, and Good Kids Sprouting Horns
- 02/09/2010 - Marie Stella and Metal Feathers
- 02/13/2010 - Dead Of Winter
- 02/18/2010 - Hillytown Presents: El Jezel, Phantom Buffalo, Metal Feathers
- 02/26/2010 - Pearl And the Beard, Sontiago, Dilly Dilly, and Lady Lamb The Beekeeper
- 02/27/2010 - Snoop Dogg
- 03/02/2010 - Jacob Augustine
- 03/06/2010 - Britney's Spear, Huak, and Jakob Battick
- 03/06/2010 - AMPM, Graph, Bunny's A Swine
- 03/11/2010 - P.O.S., Dessa, Astronautalis
- 03/26/2010 - Samuel James, Dana Gross
- 03/28/2010 - Coheed & Cambria
- 04/07/2010 - David Gray, Phosphourescent
- 04/10/2010 - Good Kids Sprouting Horns
- 05/10/2010 - Dr. Dog
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