Fiddles & Fifths Festival

Fiddles & Fifths

Get ready for an unforgettable weekend in Old Town Winchester as we send off summer with the Fiddles & Fifths Festival–a tribute to the great Appalachian tradition of bluegrass music and the homegrown taste of Virginia bourbon! This FREE street festival event on August 26 + 27 takes place in the heart of Old Town and brings world-class musical performances to our own backyard block party with all your local favorites.

Join us for headliner performances by acclaimed African-American string band EBONY HILLBILLIES and celebrated New Jersey septet RAILROAD EARTH, as well as local opener acts DUNLAP & MABE and LOW RIVER EXPRESS. Explore the great breweries, bars, restaurants, and retailers of Old Town Winchester. Or simply bring your friends and your fiddles downtown to busk in the open air!

Click here! for the event schedule.



Friday, August 26 – 4:00 PM – Bank of Clarke County Mainstage


Friday, August 26 – 7:00 PM – Bank of Clarke County Mainstage

The Ebony Hillbillies started out as an NYC street corner phenomenon, but their vibe and influence has extended over the years to acclaimed live performances at legendary venues like Carnegie Hall and Lincoln Center; appearances on the BBC, Good Morning America, NBC, CBS, etc., international music workshops and festivals, visual artist collaborations at museums (including The Whitney with phenom Kara Walker and The Smithsonian Museum), guest school programs, foot stomping and hand-clapping dance parties and more. While formed in the digital era, they have sold thousands of hard copies of their four CDs – Sabrina’s Holiday (2004), I Thought You Knew (2005), Barefoot and Flying (2005) and Slappin’ A Rabbit – Live! (2015) – at their shows and via their globally popular website. The Ebony Hillbillies are currently in the studio working on their next project.


Saturday, August 27 – 1:00 PM – The Monument


Friday, August 26 – 12:00 PM – Open Jam Session – Taylor Pavilion

Saturday, August 27 – 4:00 PM – Bank of Clarke County Mainstage

Jack Dunlap & Robert Mabe have been touring the country together since 2019; though collectively have performed and recorded with the likes of Larry Keel, Gina Furtado, Valerie Smith & Liberty Pike, Scythian, Rob Ickes & Trey Hensley, Bud’s Collective, The Fly Birds, Dry Mill Road, Old Town Flood, Shannon Bielski & Moonlight Drive, Tim and Savannah Finch and The Eastman Stringband, Lonesome Highway, Circa Blue and Jakobs Ferry Stragglers, to name a few. They have also graced prestigious stages such as The Kennedy Center in Washington, DC, Carnegie Hall in New York City, Lied Center for Performing Arts in Lincoln, Nebraska, The Hamilton in Washington, DC and Forbes Center for the Performing Arts in Harrisonburg, VA. Both masters of their instruments, they play a mix of original tunes, classic bluegrass numbers, jazz favorites and covers anyone would recognize. With roots planted firmly in bluegrass, they stretch their sound in ways that all audiences will enjoy and leave the performance wanting more.


Saturday, August 27 – 7:00 PM – Bank of Clarke County Mainstage

For over two decades, Railroad Earth has captivated audiences with gleefully unpredictable live shows and eloquent and elevated studio output. The group introduced its signature sound on 2001’s The Black Bear Sessions. Between selling out hallowed venues such as Red Rocks Amphitheatre in Morrison, CO, they’ve launched the longstanding annual Hangtown Music Festival in Placerville, CA and Hillberry: The Harvest Moon Festival in Ozark, AR—both running for a decade-plus. Sought after by legends, the John Denver Estate tapped them to put lyrics penned by the late John Denver to music on the 2019 vinyl EP, Railroad Earth: The John Denver Letters. Beyond tallying tens of millions of streams, the collective have earned widespread critical acclaim from David Fricke of Rolling Stone, American Songwriter, Glide Magazine, and NPR who assured, “Well-versed in rambling around, as you might expect from a band named after a Jack Kerouac poem, the New Jersey-built jam-grass engine Railroad Earth has let no moss grow under its rustic wheels.” The celebrated New Jersey septet — Todd Sheaffer [lead vocals, acoustic guitar], Tim Carbone [violins, electric guitar, vocals], John Skehan [mandolin, bouzouki, piano, vocals], Carey Harmon [drums, percussion, vocals], Andrew Altman [upright & electric bass], Matt Slocum (organ and piano), and Mike Robinson (banjo, guitar, steel) chronicle the twists and turns of this journey through eloquent songcraft, bluegrass soul, and rock ‘n’ roll spirit on their newest album, All For the Song.


The mainstage area will feature a number of local vendors supplying concessions during shows on Friday and Saturday. Additionally, Virginia distilleries will be on site selling craft bourbon to enjoy on-site.

Distillery offerings are made possible by our sponsors at Beach Bum Tanning.

Check back for a full list of participating vendors!


The VIP tent at the Mainstage offers the best seats in the house for all shows! Tables seat 8 and are located in the covered, fan-cooled tent adjacent to the stage itself.  Access the mainstage area before anyone else and beat the lines to visit your favorite vendors and distilleries, then kick back for a full evening of great music.

Tables are available for $1000/night on Friday or Saturday, or $1500 for both nights. To make reservations contact .

The VIP Tent is made possible by Buettner Tire Distributors, Ltd.


Join us in Old Town Winchester all weekend long for bourbon specials and festival deals at our local restaurants, bars, and breweries! With Old Town Spirit in effect from noon – 10 PM on both Friday and Saturday, you can sip, stroll, and strum your way through all the many offerings in town as you take in the great music of local Winchester area talents.

Check back for a full list of participating businesses!


Discount block rates are available for lodging through the historic George Washington Hotel at this link .