Fiddles & Fifths



Back for another year, it’s Fiddles & Fifths in Old Town Winchester!

Get ready for an unforgettable weekend as we send off summer with a tribute to the great Appalachian tradition of bluegrass music and the homegrown taste of Virginia bourbon! This returning event takes place in the heart of Old Town and brings a festival atmosphere that’s half world-class music mainstage, half backyard block party with all your local favorites.

Headlining this year is Grammy award-winning Nashville phenomenon The SteelDrivers, supported at the mainstage by local powerhouse Low Water Bridge Band and Richmond-based The Hashbury Collective. Grab tickets to take in all three performances at the concert area for one low price. 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!


Daytime events taking place from noon-4PM will be FREE to the public and located in indoor and outdoor venues across Old Town Winchester.

All Mainstage events will take place at the dedicated festival area located at Loudoun & Fairfax St, where the concert stage, VIP tent, vendor areas, and Mainstage HQ are located. Mainstage events require a general admission ($20 in advance/$35 day of event) or VIP ticket which can be purchased here. Kids 12 and under free!

Gates open at 3:30 pm and the concert kicks off at 4 with The Hashbury Collective, followed by Low Water Bridge Band at 6:15 and The SteelDrivers at 8:30.



A group of seasoned veterans – each distinguished in his or her own right, each valued in the town’s commercial community – who are seizing an opportunity to follow their hearts to their souls’ reward. In doing so, they are braiding their bluegrass roots with new threads of their own design, bringing together country, soul, blues, and other contemporary influences to create an unapologetic hybrid that is old as the hills but fresh as the morning dew. This is new music with the old feeling. SteelDrivers fan Vince Gill describes the band’s fusion as simply “an incredible combination”.

Specializing in a unique mix of what might be called bluegrass soul, the SteelDrivers have become one of the biggest names in progressive bluegrass after making their debut in 2005. While there’s a strong traditional streak in the SteelDrivers sound, they bring a passion to their delivery that adds a distinctive flavor, and they’re not afraid of adding a forceful grit to the music.

The SteelDrivers have been nominated for four Grammys, the Americana Music Association’s New Artist of the Year and was IBMA’s 2009 Emerging Artist of The Year. In 2015, “The Muscle Shoals Recordings” won the Grammy award for Best Bluegrass Recording.

The SteelDrivers are: Richard Bailey (banjo), Tammy Rogers (fiddle), Mike Fleming (bass), Brent Truitt (mandolin), and Matt Dame (guitar)



Forged by firelight picking, the band’s romping, stomping, country-grass Americana ain’t for the faint of heart. Since their founding in 2020, they’ve gone from barnstorming the Shenandoah Valley to festival stages along the East Coast. Venues from the Carolinas to Kentucky and, yes, Nashville, Tennessee ring with their sound and are asking for more.

They’re led by guitarist and lead singer Logan Moore’s searing melodies. The precision thump of brothers Alex and Riley Kerns’ bass and drums and their pitch-perfect vocal harmonies fill out the sound. Justin Carver’s pedal steel and banjo swirl through songs like smoke from the campfire.  And it’s all brought together with the crunch and crackle of James “Chainsaw” Montgomery’s electric guitar riffs.

From the first time you see them, your boots will be worn from kicking up dust. By the time a second chorus comes around you’ll be hooting and hollering their memorable originals alongside their die-hard fans. You’ll join a crowd who travels far and wide, bringing the party to your town. If you’re a fan of good music done right, be sure to keep a lookout for this fast-rising outfit from Clarke County, Virginia. Chances are, they’ll be blowing through your way one of these days soon.


The Hashbury Collective is a 6-piece band comprised of experienced musicians and based in the Richmond, VA area. A typical Hashbury show includes a heavy dose of Grateful Dead tunes mixed with other folk rock favorites from Dylan, The Band, Little Feat, Janis Joplin, and more.

Susan DePhillip: Lead Vocals, Guitar
Rob Lord: Vocals, Bass
John Leedes: Lead Guitar, Vocals
Todd Gravatt: Lead Vocals, Guitar
Tim Dunkum: Keyboards, Vocals
Rob Crosby: Drums, Vocals




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 and the craft bourbon area.  Access an exclusive dedicated audience area away from the crowd so you can kick back for a full evening of great music.

Tables are available for $1,000 for VIP and $1,500 for Super VIP and include additional perks. VIP TABLES FOR FIDDLES & FIFTHS 2023 ARE SOLD OUT! 


Created exclusively for Fiddles & Fifths, these cocktails are expertly crafted by some of our best local mixologists. Stop by these locations on Saturday and experience them for yourself!

8 item(s)

Top row (left to right): The Pineapple Agrodolce – Sazerac Rye, housemade pineapple shrub, Grand Marnier, St. Germaine, Bennett’s Bermuda Bitters, Luxardo cherry, & a dusting of organic coconut sugar (18th Rebellion); Strawberry Basil Bourbon Smash – Noble Oak Bourbon with muddled strawberries, basil, lemon juice and simple syrup topped with club soda and garnished with a basil sprig (Cork Street Tavern); Buster’s Spritz – Filibuster Straight Bourbon, Aperol, simple squeeze of fresh orange juice topped with prosecco (Ellie’s Pub Winchester); Bulleit Bourbon Gold Rush (The American Bar)

Bottom row (left to right): Basil Apple Cocktail – Basil Hayden Rye and apple cider (Willie Sutton’s Saloon); Bourbon Blunder – Noble Oak Double Oak Bourbon, Luxardo Liqueur, fresh-squeezed lemon juice, ring of jalapeño, egg white, Absente Rinse-Coupe Glass with jalapeño slice and manicured with Bittermens Orange Cream (The Wine Room at Taylor Pavilion); Smoke Bourbon Smash (Roma Old Town); Macado’s Mule – Bulleit Bourbon, ginger beer & lime (Macado’s)


Follow the links below to view lodging options in the Winchester area:

Hotels and Motels

Bed and Breakfasts






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