Destination Downtown Waynesboro

10/08/2026

The Waynesboro Winterfest Cookie Trail is back!! Kick off the holiday season with the Cookie Trail! Get your ticket now (limited tickets available) and pick up your Winterfest Cookie Trail bag on November 28 starting at 11 am at the DDW Info Booth, 503 W Main Street. Stroll around Downtown Waynesboro and pick up individually wrapped holiday cookies at 13 different businesses while you shop, sip, and dine and end up with a baker's dozen of delicious holiday cookies! ❄️🎄🍪 Tickets usually go fast, so you can grab yours now at the link!

Kick off the holiday season with the Winterfest Cookie Trail! Get your ticket now (limited tickets available) and pick up your Winterfest Cookie Trail bag on…

10/05/2026

Virginia Fall Foliage Art Show is taking over downtown this weekend October 10 & 11! Come out from 10 am - 5 pm and see over 160 artists! Have some cool vintage pics of downtown or the Show? We'd love to see them!🍂

Do you have any old photos of Downtown Waynesboro? Downtown Waynesboro during the Virginia Fall Foliage Art Show? We'd love to see them!

09/26/2026

It’s Waynesboro PRIDE!!🏳️‍🌈
We’re in downtown Waynesboro beside The Russell Museum! Live music with McHale and Justina starts at 2pm and The Hot Mamas will be on at 4pm! Free face painting with Jamie Paints starts at 1pm! Come decorate a shirt, browse some local artisans, and grab an adult beverage from one of our downtown restaurants because it’s a DORA day!🏳️‍⚧️🏳️‍🌈

09/25/2026

Meet Josh Poole, author of the Shards of Acrilon, tomorrow at Stone Soup Books from 12:30-3:00pm during PRISM!

It's going to be a beautiful day so bring a chair to watch McHale and Justina from 2-3:30 pm and The Hot Mamas from 4-6pm outside of The Russell Museum! We'll also have free face painting with Jamie Paints, a t-shirt sale and customization table, local artisan and education vendors, and more! This is also a DORA event, so go over to Delly Up and grab a drink while you enjoy a colorful day at PRISM! 🏳️‍🌈🏳️‍⚧️

Come meet the author of The Shards of Acrilon, Josh Poole, as he signs copies of his debut novel Saturday, September 26th, during the Prism Festival!

"The Shards of Acrilon is an unforgettable story of bonds forged in adventure. Ivan and Quinn are on a mission to break an ancient curse that shrouds the kingdom in a fog of forgetting. Their courage soon inspires others to join their quest, and together, the band of unlikely heroes faces fearsome adversaries. Their legendary feats would echo through the ages, if only they could be remembered. This tale of lost histories and the stories that shape us casts a spell that captivates to the very last word." — Rena Priest, Washington State Poet Laureate (2021-2023)

09/22/2026

🏳️‍🌈It's time for PRISM!!! Come downtown to The Russell Museum and the parking lot beside it this Saturday from 12-6!
🏳️‍🌈Live music with McHale and Justina at 2:00 pm and The Hot Mamas at 4:00 pm!
🏳️‍⚧️FREE face painting with Jami Paints from 1-5:00 pm!
🏳️‍🌈T-shirt customization table! Bring your own t-shirt or get a PRISM t-shirt and we'll have all the supplies to customize it! A $10 donation to DDW is appreciated!
🏳️‍⚧️Artisan vendors and educational booths!
🏳️‍🌈This is a DORA event! Bring your camp chair and grab a drink from Delly Up, The River Burger Bar, Royal India Palace, Waynesboro, VA, or Benny Stivale's!
🏳️‍⚧️And MORE!
Come as you are and leave feeling seen!

09/09/2026

PRISM is just over two weeks away on Saturday, September 26, 2026 from 12 -6pm! We are still looking for artisans and educators to set up! This is a completely free event and there is no cost to attend in any capacity including setting up a booth. We're also looking for volunteers! Please DM us if you're interested in doing either! See you there!

🏳️‍🌈🏳️‍⚧️

09/01/2026

PRISM is coming up on September 26! This year it will be from 12-6pm beside The Russell Museum with live music out front! Here's what's going on!
🏳️‍🌈Live music with McHale and Justina at 2:00 pm and The Hot Mamas at 4:00 pm!
🏳️‍⚧️FREE face painting with Jami Paints from 1-5:00 pm!
🏳️‍🌈T-shirt customization table! Bring your own t-shirt or get a PRISM t-shirt and we'll have all the supplies to customize it! A $10 donation to DDW is appreciated!
🏳️‍⚧️Artisan vendors and educational booths!
🏳️‍🌈This is a DORA event! Bring your camp chair and grab a drink from Delly Up, The River Burger Bar, Royal India Palace, Waynesboro, VA, or Benny Stivale's!
🏳️‍⚧️And MORE!
Come as you are and leave feeling seen!

We do need volunteers! If you're interested please DM us!

***This event is 100% free and does not have a vendor fee. Destination Downtown Waynesboro NEVER accepts vendor fees online. Please be aware of those trying to secure vendors for this event and are charging a fee***

07/11/2026

The show will go on! Come see us Waynesboro Parks and Recreation’s GloW show and get some light up cups, glow sticks, and decorate a t-shirt!

All proceeds go towards helping us bring Waynesboro amazing programming like Winterfest, the Virginia Street Arts Festival, and more!

07/10/2026

We'll be at GloW Waynesboro tomorrow with Waynesboro Parks and Recreation! Come see us to decorate a t-shirt and pick up a color change cup with a light and glow sticks. We had a great time last year! We'll also have a water station!

Proceeds go to Destination Downtown Waynesboro so we can have fun events like Prism (September 26) and Winterfest (November 28) and support and promote Downtown Waynesboro!

06/30/2026

This is for you, downtown Waynesboro! Get new awnings, signage, paint, or other improvements!

Give your building the makeover it deserves with the Building Improvement Grant💅 Eligible businesses in Downtown and Rockfish Gateway can receive up to $5,000 in reimbursable grant funds for projects like:
🎨Paint
🏬New awnings
🪧Signage
🌿Landscaping and hardscaping

Learn more, check your eligibility, and apply at https://waynesborobusiness.com/local-business-resources/building-improvement-grants/