Fiddles & Fifths - Bluegrass & Bourbon Festival

12/30/2025

📅 September 12, 2026 ~ Save the Date for the 5th annual Fiddles and Fifths Bluegrass and Bourbon Festival!

Stay tuned for more details… you won’t want to miss this event!

09/12/2025

09/12/2025

Tomorrow!

09/12/2025

The Cider House (@winchester_cider_house ) has a specialty menu for Fiddles & Fifths! Make sure you check them out! 🎉🎉🥃🔥

09/11/2025

Come see us this Saturday, September 13th, during Wi******er’s Fiddles & Fifths - Bluegrass & Bourbon Festival! We’ll have our Bourbon Barrel Vienna Lager on tap, plus co****le set up outside. And of course, downtown will be full of great music and bourbon tastings all day long.

09/11/2025

09/10/2025

Need a quick update to all the details for Saturday? See below! 🎉🎉🥃

Is there a ticket cost?
• No, this is a FREE, family-friendly (at your discretion) event! All music will be at a stage in front of the Shenandoah Valley Civil War Museum, 20 N. Loudoun Street, Wi******er, VA 22601.

Will there be merchandise to purchase?
• Yes! You can purchase Fiddles & Fifths merch at the Bright Box Theater, including T-shirts, bottle openers, glasses, and more.

How does the Distillery Area work?
• The Distillery Area is a non-ticketed area. Anyone older than 21 years old is welcome to visit the Distillery Area. IDs will be checked by Security at the front gate.

Where can I park?
• Street parking is available, plus there are four parking decks around the downtown Walking Mall open during the event.

More parking info here: https://www.winchesterva.gov/Serv.../Streets-Traffic/Parking

Where are the restrooms?
• Portable restrooms will be available on Boscawen Street next to the Distillery Area.

Can I bring my own chairs or tents?
•No portable chairs or tents are allowed to keep the Walking Mall clear for pedestrians.

Can I bring my pet?
• Non-service animals are not allowed inside Bright Box Theater or the Distillery Area. All pets must be leashed while on the Walking Mall. Please be kind and clean up after your pet!

Where is alcohol allowed?
• The Designated Outdoor Refreshment Area (DORA) program will be in effect. Patrons 21+ can purchase alcohol from participating venues and enjoy it outdoors within the marked DORA boundaries.

Open alcohol outside the DORA area is prohibited. No alcohol is permitted to be carried in or out of the Distillery Area. Learn more about DORA here: https://friendsofoldtown.org/events-in-old-town/dora-information/

09/10/2025

🥃 Lots of local restaurants are participating this Saturday in crafting bourbon & southern-inspired drinks and culinery delights for Fiddles & Fifths! 🥃

09/09/2025

Playing a special Busking set for Fiddles and Fifths this Saturday 9/13 from 3-5:30pm towards the North Side of the walking mall!

09/08/2025

Only 🔥5🔥 days away! Join us for this FREE EVENT in Old Town Wi******er VA for , @brennanedwardsmusic , and Reno & Dunlap!

Over 10 distillery partners from throughout the Shenandoah Valley and beyond will be on site!

09/07/2025

FREE EVENT for this year’s 2025 Fiddles & Fifths Bluegrass & Bourbon festival!

See you in Old Town Wi******er Saturday September 13th! 🥃🥃🥃

09/06/2025

SOLD OUT!

We have currently sold all of our seats for the Heaven Hill Bourbon Dinner on Friday, September, 12th! We can create a wait list if anything changes!

Cheers! 🥃