Waynesboro’s calendar is stacked with festivals, live music, public art, cold drinks, and brook trout. Are you… Hiker trash chasing a cold beer? An artsy type with paint under your nails? An IPA critic with strong opinions? A self-proclaimed foodie? A parent desperately looking for something new and different for your kid? Or just a normal human who likes a good time? Don’t worry, you’ll fit right in right here in Waynesboro during…FESTIVAL SEASON.
Riverfest | May 2 | Constitution Park
We’re kicking things off right with Riverfest 2026 – Year of the Brook Trout! If you don’t know what that means, then keep reading, you’ve obviously never been to Riverfest. 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).
Waynesboro Farmers Market | Every Saturday from May 9 – October 31 | 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 local goods.
Virginia Street Arts Festival | May 16- 17 | Downtown Waynesboro
Get ready to watch art come alive! Renowned muralists will be transforming six 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, guided art tours, and more. Added bonus: this a DORA event, so take your drink with you while you take in some culture and listen to live music.
Tour the Town | May 27 | 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 fifth (I can’t believe this has been around for five years!) 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! Stay tuned for more info and tickets!
Hiker Fest | June 5-6 | Downtown Waynesboro
Celebrate the Appalachian Trail and all things outdoors during the fourth annual Hiker Fest. This year, we’re ramping things up a little and rolling out the red carpet for the 2026 AT thru hikers. Start your weekend by hopping off the AT on Friday, June 5 at Rockfish Gap (that’s mile 876.9, if you’re counting) for some trail magic sponsored by McKee. 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 get some dinner 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. See you there!
PRISM: Waynesboro Pride | September 5 | 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!
Chili, Blues, and Brews | September 12 | Lumos Plaza
Think your chili recipe could win it all? Time to find out. The Virginia Chili Blues & Brews Festival is basically a full day of people taking chili very seriously, plus live blues and plenty of cold beer to keep things interesting. You’ll get to sample your way through a whole lineup of teams competing for bragging rights and prizes. Come hungry, pace yourself, and don’t be surprised if you leave convinced you should enter next year.
Outdoor Concert (and ice cream? And running?) Series
Groovin’ at the Greenway | Thursdays, May 7 – July 2 | 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 there are also food trucks and drinks, so bring your chair and enjoy the show! Stay tuned for the line up!
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 (in February, so plan ahead) lets you get super dirty while braving an obstacle course while also 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
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. 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 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 28 | 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, Princesses, the Grinch, BINGO, and lots of other festivities to kick off the holiday season – unless you’re my coworker, in which case that starts sometime in October…
