Fiddles & Fifths - Bluegrass & Bourbon Festival

09/21/2026

A big thank you to Black Shirt Bourbon Society for featuring this year’s Fiddles & Fifths Festival in their latest video!

From live bluegrass on the streets of Old Town Wi******er to tastings from Virginia distilleries, the video captures what makes this festival so special—great music, craft spirits, and a great community atmosphere.

Check it out and relive the fun from September 12! 🎻🥃

Give them a watch and a follow!

https://youtu.be/-ImHJXuPX8o?si=oSXI9qQb3wPANA1z

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09/15/2026

🎻🥃 What. A. Day. Wi******er!

A huge THANK YOU to everyone who came out for the 5th Annual Fiddles & Fifths!

Thank you to our amazing performers, distillers, vendors, volunteers, sponsors, partners, We couldn’t have done it without you!

A massive THANK YOU to everyone who came out and spent the day with us in Downtown Wi******er. Cheers! 🥃🎻❤️

Photo Credits: Lexy Sacco

09/11/2026

🥃🎻 ONE DAY AWAY! 🎻🥃

Tomorrow, Fiddles & Fifths – Bluegrass & Bourbon Festival takes over Old Town Wi******er!

🎶 Live bluegrass starting at 1:30 PM
🥃 Distilleries from around Virginia, 1–7 PM
🍽️ Food, drinks & DORA
🎟️ Free admission

Bring your friends, grab a drink, and settle in for an afternoon of bluegrass, bourbon, and good times in Old Town!

📍 Old Town Wi******er
📅 Saturday, September 12
⏰ Music starts at 1:30 PM

We’ll see you tomorrow! 🤠🥃🎶

09/09/2026

👀 Have you heard? Fiddles & Fifths is making headlines!

Thanks to The Wi******er Star for helping get the word out about this Saturday’s festival.

Give it a read then come downtown and experience Fiddles, Fifths & all the fun for yourself! 🎻🥃

On Saturday, Wi******er celebrates the fifth annual Fiddles and Fifths festival. Headlining this year's event, which is sponsored by the Wi******er Economic Development Authority in partnership with Bright Box Theater and Nick Helmut Presents, is The Creekers, one of the hottest bluegrass bands currently on the circuit.

09/09/2026

💿 Fiddles, Fifths & 33⅓s! 🥃

We love seeing our Old Town businesses get in on the Fiddles & Fifths fun!

This Saturday, while you’re downtown enjoying live bluegrass and bourbon, make sure to stop by Back to the Media - Video Games Music & Movies and dig through their fresh stack of Bluegrass, Americana, Roots, Outlaw Country and more. 🎶💿

Make a day of the music, bourbon & vinyl. 🥃💿

📍 Old Town Wi******er
📅 Saturday, September 12

🎻 Fiddles, Fifths & 33⅓s💿

Fiddles & Fifths is taking over Old Town Wi******er this Saturday, and obviously we needed to get in on the fun.

We’re moving our Bluegrass section front and center and bringing in a fresh stack of new vinyl for the weekend: Bluegrass, Americana, Roots, Outlaw Country and all the good stuff in between.

We’ve got Billy Strings, Tyler Childers, Sierra Ferrell, Molly Tuttle, Sturgill Simpson and more headed to the bins, plus plenty of used records already here waiting to be dug through.

So while you’re downtown listening to live music (and maybe sampling a little bourbon 👀🥃), wander into Back to the Media and do some digging.

Saturday, September 12 • Old Town Wi******er

Come for the fiddles. Stay for the 33⅓s.

09/09/2026

🎶 Q102 IS TURNING IT UP FOR FIDDLES & FIFTHS! 🥃

A HUGE shoutout to Shenandoah Country Q102 / iHeartRadio for being our Marketing Sponsor and helping us spread the word about the biggest bluegrass & bourbon party in town!

From the airwaves to the festival grounds, Q102 is helping bring Fiddles & Fifths to music lovers across the Valley! 📻🔥

So turn up Q102, then come turn up with us!

📅 Saturday, September 12
📍 Downtown Wi******er
🎸 Live Bluegrass • 🥃 Bourbon • 🎉 FREE Festival

Thanks, Q102, for helping us make some noise! 🤠

******erVA

09/09/2026

👖 Need a new ‘fit for Fiddles & Fifths?

Stop by Revival Vintage Co. and find the perfect vintage look to bring to the festival! 🎶🥃

Because great bourbon deserves a great outfit. 😉

📅 Fiddles & Fifths – September 12
📍 Downtown Wi******er

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09/09/2026

🍽️ Don’t wait, make those reservations ASAP!

You do not want to miss this incredible menu prepared by Village Square Restaurant and V2 Oyster Bar & Lounge for Fiddles & Fifths!

Seats are limited, so reserve your spot now and get ready for an unforgettable evening of great food, bourbon & bluegrass! 🥃🎶

📅 Friday, September 11
📍 Downtown Wi******er

09/08/2026

🥃🎶 KNOW BEFORE YOU GO!

We’re just days away from Fiddles & Fifths – Bluegrass & Bourbon Festival! Before you head downtown, here’s everything you need to know to make the most of your day:

🎟️ IS IT FREE?
YES! Fiddles & Fifths is a FREE event! Enjoy live music at the stage in front of the Shenandoah Valley Civil War Museum, 20 N. Loudoun Street.

👕 MERCH? ABSOLUTELY.
Grab your Fiddles & Fifths gear at Bright Box Theater, including T-shirts, bottle openers, glasses & more!

🅿️ WHERE CAN I PARK?
Street parking is available, along with four parking garages around the Downtown Walking Mall.
👉 More parking info: https://www.winchesterva.gov/Serv.../Streets-Traffic/Parking

🚻 RESTROOMS
Portable restrooms will be available on Boscawen Street next to the Distillery Area.

🪑 CAN I BRING A CHAIR OR TENT?
Please leave the lawn chairs and tents at home! Portable chairs and tents are not permitted so we can keep the Walking Mall clear for pedestrians.

🐾 CAN I BRING MY PET?
Pets are welcome on the Walking Mall as long as they are leashed — but non-service animals are not permitted inside Bright Box Theater or the Distillery Area. And please remember to clean up after your furry friend!

🥃 WHERE CAN I DRINK?
The Designated Outdoor Refreshment Area (DORA) will be in effect! Guests 21+ can purchase alcohol from participating venues and enjoy it outdoors within the marked DORA boundaries.

🚨 Important: Open alcohol is prohibited outside the DORA area, and alcohol cannot be carried into or out of the Distillery Area.

Learn more about DORA: https://friendsofoldtown.org/events-in-old-town/dora-information/

🎶 Now you know — all that's left is to come enjoy the festival!

📅 Saturday, September 12
📍 Downtown Wi******er
🥃 Bourbon • 🎸 Bluegrass • 🛍️ Shopping • 🎉 FREE ADMISSION

See you downtown!

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