Waynesboro’s calendar is packed with festivals, live music, public art, cold drinks, and plenty of excuses to eat ice cream. It doesn’t matter if you’re hiker trash in need of a cold beer, an art aficionado with paint under your nails, a craft beer snob rating every IPA out of 10, a foodie on a first-name basis with Coq au Vin, a live music fan who always knows the lyrics, or just a solid human who likes a good time—Waynesboro’s definitely where you want to be.
Riverfest | May 3 | Constitution Park
We’re kicking things off right with Riverfest 2025 – Year of the Eastern Box Turtle! Riverfest is Waynesboro’s celebration of environmental conservation and the South River. Activities include Reptile World shows, presentations by the Wildlife Center of Virginia, Stream Safari exploration, Fish and Fun Rodeo, canoe rides, kids’ arts & crafts, interactive exhibits, and more. The day ends with the Great South River Duck Race (ever seen thousands of rubber duckies race down a river? No? You should).
Wings Over Waynesboro | May 12 | Sunset Park
If you’re a local who hasn’t been living under a rock for the past year, you’ve probably heard of Sunset Park, and you may have heard of Wings Over Waynesboro, which is coming back in 2025. This year it’s bringing back all the good stuff: live music, BBQ from LFA Catering and Sooner BBQ, local beer from the Blue Ridge Beverage truck, Lucky Duck kettle corn, and Noila’s Lemonade for the N/A crowd! Come hungry, come thirsty, and bring a lawn chair—you’ll want to stay awhile.
Waynesboro Farmers Market | Every Saturday from May 10 – October 25 | Constitution Park
Fresh produce, local meat, baked treats, food trucks, activities, and live music make every Saturday morning feel more like a festival than your average, everyday farmers market. Grab a coffee, stroll the vendors, and stock up on some flavor.
Virginia Street Arts Festival | May 17- 18 | Downtown Waynesboro
Get ready to watch art come alive! Renowned muralists will be transforming three downtown walls into massive works of art right before your eyes. And as cool as that sounds, there is so much more happening during the festival that I had to write a whole separate itinerary just for that weekend. A mobile museum park, live music, interactive art experiences, community art projects, and more. Added bonus: this a DORA event, so take your drink with you while you take in some culture.
Tour the Town | May 28 | Downtown Waynesboro
If you’re lucky enough to live in Waynesboro, then you clearly make excellent life choices and should reward yourself by getting a ticket to the fourth annual Tour the Town. This unique event invites you to explore downtown Waynesboro by stopping in at 20 participating Restaurants, shops, galleries, and museums to sample their food and drinks (this is also a DORA event, so take that cocktail on the go!), score some free gifts and special discounts, and more! You can get your ticket and all the details here.
Hiker Fest | June 6-7 | Downtown Waynesboro
Celebrate the Appalachian Trail and all things outdoors during the third annual Hiker Fest. This year, we’re ramping things up a little and rolling out the red carpet for the 2025 AT thru hikers. Start your weekend by hopping off the AT on Friday, June 6 at Rockfish Gap (that’s mile 876.9, if you’re counting) for some trail magic. The Appalachian Long Distance Hikers Association and Waynesboro Tourism will be hosting a hiker feed and shuttles from 8 am – 4 pm. Once you’ve made your way into town check out some live music at Delly Up and enjoy free camping downtown.
Saturday, thru Hikers can start the day out at the Russell Museum with free breakfast and everyone is, of course, welcome at the festival. Live music all day, food, local beer and wine, free yoga practice, henna, outdoor vendors, and special presentations by Warren Doyle and Ms. Janet (plus more I’m probably forgetting). See you there!
PRISM: Waynesboro Pride | September 6 | 522 W Main Street
PRISM is Waynesboro’s inclusive, vibrant Pride celebration—complete with live music, art, food, and community love. Whether you’re out, proud, or an ally, it’s a joyful, welcoming day that shines bright in our festival lineup. Stay tuned for more details!
Outdoor Concert (and ice cream? And running?) Series
Groovin’ at the Greenway | Thursdays, May 8 – July 3 | Constitution Park
Every Thursday night, the South River Greenway comes alive with a free concert in the park. Grab a blanket or lawn chair, pack your cooler, and bring the kids (there are free kid’s activities with BRCM!) and let local bands provide the soundtrack to your summer. Also, forget cooking – there are food trucks there every week!
Wayne on Main | Last Wednesdays, May – August | In Front of the Wayne Theatre
The Wayne’s outdoor concert series always delivers and this year they’re starting the season off with everyone’s favorite, Sundried Opossum! There are also food trucks and drinks, so bring your chair and enjoy the show!
Kickin’ Back with Klines | Last Sundays, June – August | Sunset Park
It’s simple: ice cream, sunsets, live music, and good company. On the last Sunday of each summer month, Waynesboro’s favorite scoop shop heads up the hill to Sunset Park for a laid-back festival with music and treats. It’s the perfect excuse to lean into that summer sweetness.
Run the Valley Series | All Season Long | Multiple Locations
If you like your festivals with a side of exercise (it’s not for me, but cheers to those who do it!) Waynesboro’s Run the Valley series is calling you! Scenic races like the Park to Park Half Marathon and Fall Foliage 10K let you earn a post-run beer in the most beautiful way possible, and the Mad Anthony Mud Run lets you get super dirty while braving an obstacle course while dressed up like a Revolutionary War General in a dog park? It might sound out there but it’s a popular one! Plan your trip and pair it with a race!
Later in the Year
Chili, Blues, and Brews | September 13 | Lumos Plaza
Spicy chili. Craft Beer. Live Blues. What more do you need on a Saturday? This classic Waynesboro event brings the heat (literally) to downtown Waynesboro and lets you get in on the action by voting for your favorite chili!
Fall Foliage Art Show | October 11-12 | Downtown Waynesboro
This is the granddaddy of all the Waynesboro festivals. It’s been around the longest. It’s the biggest. And it’s the only one where all the streets downtown are closed for the entire weekend (which is a big deal, trust me). Every year on the second weekend in October you can come to Waynesboro to browse over 150 fine artists who descend on Waynesboro to turn it into the gallery of your dreams. Plus, there’s beer and live music. You can feed two birds with one scone (I know, I know. I heard this alternate idiom the other day and it just seems so much more…humane) on this fall weekend and catch the foliage while you attend an awesome (and free) festival in our picturesque mountain town.
Winterfest | November 29 | Downtown Waynesboro
We wrap the festivals up in Waynesboro with a holiday bash that makes Hallmark movies envious. We combined good ol’ fashioned holiday traditions like wassailing, caroling, and pictures with Santa (all while a snow machine pumps out fake snow all day to really get you in the mood) with a cookie trail, pet portraits, the Grinch, BINGO, and lots of other festivities to kick off the holiday season – unless you’re my coworker, in which case that started sometime in October …
