* Ranked in top 50 Gifted Singer-Songwriters You MUST Know by Riff Journal   
* PARADOX Voted BEST ALBUM of 2019 in Cleveland Scene Magazine   
* Music Connection Magazine 2019 Album Review of PARADOX 


“If you don't believe an acoustic solo performance can fill a room with raw power, and intelligence concurrently, you haven't experienced Diana Chittester”   

Diana Chittester has been building a reputation as one of the area’s most gifted guitar players, intimate songwriters, and forceful vocalists over the past decade, releasing a series of albums that display her growing confidence and ability to communicate feelings that are deeply personal yet universal. 

Diana has shared the stage with Lyle Lovett, Gin Blossoms, The Accidentals, Joan Osborne, Peter Mulvey, Chris Trapper, Lisa Loeb, and Colin Hay; performed at venues across the eastern U.S. and Canada including Kent State Performing Arts Center, City Winery DC, Showplace Performance Centre, Evening Muse, Cain Park, Music Box Supper Club, and The Ark; performed on Woodsongs Old Time Radio Hour and Songs at the Center which airs on PBS.

"Like Michael Hedges and Ani DiFranco, Chittester is a master guitarist who employs open and alternate tunings—and provides her own percussion on the body of her instrument." 

Dubbed a “Guitar God” by Skinny Devil Magazine and “a complex guitar acrobat” by ArtVoice Magazine, in 2017 she was invited to perform on the "Cellar Sessions" series recorded live at City Winery in NYC. 

 "Cleveland artist Diana Chittester has a high-register vocal tone that’s a good match for her often uke-fueled material, which is captured by production that allows every word to come through loud and clear. We like the subtle versatility in this artist, as well. She can be spry and upbeat, sounding almost like a Disney princess on the inspirational “Freedom,” then she can shift to a heavier, bluesy, slide guitar-infused “In The Middle” before delivering a touching, heart-tugging, grown-up ballad, “Paradox,” wherein she muses thoughtfully on the nature of love, trust and fidelity. Chittester’s natural versatility and wide vocal range are captivating."  


Diana Chittester brings emotional testimonies meant to challenge perspectives and the definition of reality with her latest full-band release, PARADOX. The 6-song EP has hit the Americana Music Charts, receiving national airplay from over 50 stations across the US and Canada. The first track "Freedom" made its way onto popular Spotify playlists including American Top 40's. 

“...with its powerful vocals, [Paradox] recalls Tigerlily-era Natalie Merchant”



► Since 2021, received over $65,000 in grant funding to teach art-based curriculum to prepare high school students for higher education, or a career path, as a professional artist in the music industry 
► Accepted as a Teaching Artist with the Ohio Arts Council in 2020 

► Paradox (2018) won 2019 Best Local Album in Cleveland Scene Magazine 
► Named one of the “Top 50 Gifted Singer-Songwriters You MUST Know” by Riff Journal in 2019 
► Official music video for Paradox was selected for the 43rd Cleveland International Film Festival Official Film Selection
► Diana Chittester opened for Lyle Lovett, 2019
► The Diana Chittester band opened for Gin Blossoms, 2019
► Tour with Chris Trapper (of the Push Stars), 2018 
► Special guest performer, Rock & Roll Hall of Fame Induction Celebration, 2018 
► 1st Place Winner: “Rock Like Rosetta [Tharpe]” Competition, 2018 
► “Freedom” featured on multiple Spotify playlists, May 2018 
► Featured performer at Cleveland's first contemporary music festival, LaureLive, 2016

DOWNLOAD Promo Headshot Photo by: Every Angle Photography 670 KB 
DOWNLOAD Promo w/ acoustic guitar Photo by: Every Angle Photography 1.06 MB 
Stage Plot - SOLO

media quotes

“If you don't believe an acoustic solo performance can fill a room with raw power, elegance and intelligence concurrently, you haven't experienced Diana Chittester” 

       - Jennifer Conn (The Devil Strip)

"Like Michael Hedges and Ani DiFranco, Chittester is a master guitarist who employs open and alternate tunings—and provides her own percussion by rapping on the body of her instrument." 
      - (from Colin Hay review)

“Diana really connected with the audience with her lyrics, guitar playing and great
energy. Her storytelling & explanations of her songs resonated thoroughly, receiving a
great ovation & an encore for her opening set, which I haven’t seen before.”
     – Arnie Ivsins (Barrie Folk Society, Canada)

  “An intelligent and articulate artist”
     – Music Connection Magazine

  “Demonstrated prowess on the guitar and [a] penchant for wrenching vocals.”
     – Cleveland Plain Dealer

  “She is one woman, one guitar, and no gimmicks…and she is one of THE most
important artists on the scene in years, and one to watch closely for years to come.
And, for guitarists, one to study closely…”
     – Skinny Devil Magazine : Guitar Gods: LIVE

   “A complex guitar acrobat”
     – ArtVoice Buffalo

   “Her lyrics both delve into stories and are fearless in its questioning with an intense
guitar style backing it up”
     – Her Society, Joy 94.9 (Australian Radio)