Schedule of Events

Virtual Marketplace Open 7/27 through 8/10.

Virtual Music Festival 8/1



The Bands

2:45 – 3:30 PM – The Quires

4:00 – 4:45 PM – Definitely Pinwheels

5:15 – 6:00 PM – Brassfield

6:30 – 7:15 PM – The Rumors



Check out our live event on Facebook!

How can I support?

We’d added the artist’s and presenter’s virtual tip jars to their bios below so you can send some love to the people who’s sets inspired you and got you moving and grooving at home. Support your favorite Festival vendors in our Virtual Marketplace and check out the great deals they have going on currently.

If you’d like to support the St. Matthews Street Festival directly you can reach out to the Chamber of St. Matthews to find out how.

The Quires


Sheila has been singing since she was a young girl. Once known as the Loretta Lynn of Logan County, she began her singing career singing bluegrass.  Today, she enjoys singing all types and styles of music.  When Sheila and Jack married in 1981, Jack began to learn the guitar from Sheila’s father, Jay Anderson, a well know bluegrass singer/musician in South Central Kentucky. These days, Sheila and Jack share their music with residents of Assisted Care Communities, Cancer patients in Oncology Offices, their church and church band, and on Facebook. They enjoy sharing the songs that mean the most to them, primarily from the 70’s and 80’s.  

We don’t necessarily want tips, but thanks!  Leave us a message if you like our music!  Tell us what you think we should do if you don’t!  You can contact us at 

Definitely Pinwheels


Romana Bereneth and Stephen Phillips are Definitely Pinwheels, a jazz-inspired duo based in Louisville, KY. Romana’s witty songwriting and Stephen’s keen guitar skills combine to create an exciting acoustic show whether online or in person. Both musicians possess experience across multiple genres and instruments, including swing, jazz, classical, Middle Eastern, metal and surf rock. The sound of Definitely Pinwheels is a marriage of their love for “Django style” jazz, powerful songwriting and intricate improvisation.  

Romana and Stephen originally formed Definitely Pinwheels earlier this year to continue pursuing musical goals while socially distancing from their four-piece, Bandshee. However, the two have worked closely in multiple projects since 2018. Ever hard working and driven musicians, Stephen and Romana have already recorded and published their first EP “Evil Mysterious Darlin’” available on Bandcamp and look forward to recording their first full-length album with Bandshee later this year. Definitely Pinwheels has played live streams and virtual festivals such as Aubryn’s Online Festival, SAFE, and Socially Distant Festival. The duo has been invited to play several shows and festivals in the coming months, fate willing. Whatever happens, these two will DEFINITELY be playing bold and eclectic tunes somewhere in the Bluegrass. Check out their EP “Evil Mysterious Darlin” on Bandcamp! 

Tips can be sent to Paypal via or Venmo at @Stephen-Phillips-74.


BRASSFIELD is a country vocal trio based in Nashville, consisting of brothers Bradley and Chadley Brassfield, and Chadley’s wife, Jessie Rose Brassfield. It’s certainly a family affair that makes for airtight three-part harmonies and a stellar vocal blend. Musical roots run deep for all of them. The brothers were born in Tupelo, Mississippi, where music is certainly a way of life. In the Brassfield bloodline, being a great singer is commonplace and the boys are no exception to this phenomenon. Growing up, they toured the southern US playing and singing in churches, fell in love with being on stage, and knew that they wanted to continue their career together in Nashville. That’s where they met Jessie Rose. Born and raised in Lexington, Kentucky, Jessie has spent her whole life in a musical bubble. She’s been a happy student of music from the start and the love and curiosity spreads across all genres. She’s been singing, playing piano, and writing songs for as long as she can remember. She comes from a long line of professional singers/musicians/writers, her dad being JP Pennington of the country hit-making group Exile.

Following in his footsteps, she moved to Nashville to pursue country music, met the boys, the stars aligned, and two very important things happened. Jessie and Chadley fell in love, and the trio discovered that their three unique voices came together to form a killer vocal blend. The rest is history. This in-demand trio performs all the time, sometimes seven days a week. They are the house band for The Opry Backstage Grill, where they host a hit songwriters night that has put them on the stage with many of country music’s most prolific songwriters. All three members of BRASSFIELD are songwriters themselves and are beyond thrilled to be bringing their music to life with legendary producer Paul Worley. For more information, you can find BRASSFIELD on Facebook, Instagram and Twitter at @brassfieldmusic.

Tips can be sent via Paypal to or Venmo to @brassfield-music.


The Rumors

Based in Southern Indiana, The Rumors have been performing throughout the Midwest region since 1994.  The Rumors specialize in festivals, wedding receptions and corporate events.  Covering a wide range of musical genres and eras, audiences of all ages are sure dance and sing along!  The band’s commitment to professionalism, top-notch audio and lighting equipment ensure that every live music event is a certain success.

Tips can be sent to Venmo at @TheRumors.