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Jimmy O

At the winery 2300 Whipper In Lane, Keswick, VA, United States

For over 45 years, Virginia entertainment icon “Jimmy O” has had a mission. His motto, Preserve Endangered Music, says it all. Hear the greatest, the frequently unexpected, and always, the […]

Ian Vest

At the winery 2300 Whipper In Lane, Keswick, VA, United States

Ian Vest is a 26-year-old country singer/songwriter who hails from Southwest Virginia. Ian has a throwback style of country music that is reminiscent of those like George Strait and Randy […]

Cake Fight

Cake Fight is a fun, energetic modern pop and classic rock cover band that plays everything from Dua Lipa to Devo to the Doors. So, everyone from your teenage niece […]

Vinyasa in the Vines

At the winery 2300 Whipper In Lane, Keswick, VA, United States

Experience the perfect fusion of yoga and nature with a tranquil Vinyasa in the Vines session at Southwest Mountains Vineyards. Led by certified yoga instructor Brian Franke, this invigorating class […]

Chris Rentch

Chris Rentch, a talented Virginia native, captivates audiences with his smooth vocals and repertoire of Country and Americana songs from various eras.

Regan & Westlyn

At the winery 2300 Whipper In Lane, Keswick, VA, United States

Regan & Westlyn is a music duo (guitar/piano/vocals) whose repertoire includes a mix of pop/rock, singer/songwriter tunes, jazz standards, originals, and a bunch of other stuff we just like. 

Paulo Franco

At the winery 2300 Whipper In Lane, Keswick, VA, United States

Paulo Franco plays original songs (and covers) in both English and in Spanish.  He switches his voice from country twang, to rock anthem, to Spanish troubadour with ease.  His vocals […]

Gina Sobel & Matt Draper

Multi-instrumentalist duo Gina and Matt bring their high-energy Americana, blues and acoustic jazz to the stage. Get ready for fun, creative covers as well as compelling original tunes, and lots […]

Matty Metcalfe

At the winery 2300 Whipper In Lane, Keswick, VA, United States

Matty Metcalfe is a classically trained pianist and guitarist whose musical interests in his teenage years branched out towards jazz, blues, pop and ‘world’ music. During that time, he also […]

John Kelly

At the winery 2300 Whipper In Lane, Keswick, VA, United States

John Kelly is a Charlottesville-based singer-songwriter with more than two decades of solo acoustic performing experience. Now a regular on the Central Virginia singer-songwriter circuit, John has become known for […]

Danny Jams

At the winery 2300 Whipper In Lane, Keswick, VA, United States

Danny Jams is a one-man band that grooves like no other. Based in Richmond, VA as a full time performer, Danny is a multi-instrumentalist singer and songwriter that performs a […]

Bomar & Ritter

At the winery 2300 Whipper In Lane, Keswick, VA, United States

Mary Bomar & Bob Ritter have been performing together for over 34 years.  Their style of acoustic singer/songwriter, folk rock and pop music, and their easy-going stage manner has made […]