Skip to content

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 most loved classic music from the 50s to the 90s soulfully and compellingly interpreted by the unique voice and guitar of Jimmy Overton. No two […]

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 Travis.

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 to her grandfather will be dancing and singing along to their favorite songs.

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 invites you and your friends to embrace the serenity of the vineyard and bask in the beauty of the morning sunrise. Enhance your experience further […]

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 are so authentically Spanish that it's easy to forget you just heard him effortlessly sing a country tune in English

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 of different instruments!

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 began studying the accordion, banjo and mandolin, all of which led to opportunities to play with some of the biggest regional and international folk acts […]

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 his soulful voice and insightful original songs.

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 jam packed set of classic rock & soul covers along with some captivating originals of his own.

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 them a favorite act of venues and guests from the Midwest through the East Coast states.