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Top 15 Things to Do in September and October Near Waynesboro

The Waynesboro events calendar is full of fun things to do in September and October. You will find everything from festivals to dancing to cars to bike rides. Plan your Iris Inn getaway around one of these fun activities.

Steal the Glass at Stable Craft Brewing, Wednesday, September 6, 4pm-9:30pm – So the name of the event is a little misleading. You will not actually be stealing anything. The brewery is giving away stoneware mugs with any beverage purchase. The camping themed mug encourages you to “Get Out” and enjoy the outdoors. Items like mugs are fantastically practical souvenirs because you will use them instead of letting them gather dust on a shelf. An added bonus is that you will think about your trip every time you use it. The brewery serves hand-crafted beer, wines, ciders, and sodas in a biergarten-style atmosphere.

  1. Salsa and Bachata Lesson and Dance, Friday, September 8, 5pm-9:30pm – Stable Craft Brewing loves having events at the brewery. Join them for a free salsa and bachata lesson from 5-6pm, then dance the night away while enjoying dinner and drinks under the stars. You will be burning calories while you dance so go ahead and order the scrumptious beer cheese dip.
  2. Valley Veterans Ride for Heroes, Saturday, September 9, 8:30am – Bring your bicycle and challenge yourself to one of five distances: two gravel loops of 19.5 or 45 miles, and three road loops totaling 26, 43, or 64 miles. The scenic routes traverse rolling hills and may include up to 3,905 feet of climbing. The ride benefits Boulder Crest Retreat which works to enhance the holistic well-being of military personnel, veterans, first responders, and their families. The event is hosted by Stable Craft Brewing. Enjoy a cold beer after finishing your ride.
  3. Kitchen Takeover with Chef Curtis Wright, Friday, September 15, 6pm-8pm – For one night only, The City Foxes (wine bar and market) and Smokehouse Cafe (soul food BBQ fusion restaurant) will join forces for a kitchen takeover. Watch as Chef Curtis shares his culinary techniques while creating a full meal for attendees. The $70 fee includes a pre-fixe menu and wine pairings.
  4. Margarita 5K, Saturday, September 16, 9am – If you are a runner, you know how much fun it can be to run in a new place. If you are not a runner, come see what the fun is all about. The 3.1-mile course is walker and dog friendly so you can bring the whole family. All participants receive a performance race shirt, a finisher glass, and a margarita (for those over 21). Get in a little exercise then hang out at the after party. You will still have the whole afternoon to explore something else in Waynesboro. Or you can take a nap and head back out for evening festivities. The 5K is sponsored by Plaza Antigua in honor of National Hispanic Heritage Month.
  5. Virginia Chili Brews and Blues, September 16, 12pm-9pm – The 13th annual Virginia Chili Brews and Blues is sure to satisfy your taste buds. Chefs can start checking in for the festival at 8am. Once they have their table set up, they can start cooking. This is a true test of culinary skills since nothing can be pre-cooked. Samples will be collected for the judges at 3:30pm with public tastings beginning at 4pm. The cost to enter as a chili chef is $100 but the top prize is $1,000! Not a chef but really enjoy eating chili? General admission tickets start at $20. The gates open at 12pm and there will be live music from 2pm-9pm. Bring your dancing shoes and an empty stomach.
  6. African American Heritage and Multicultural Festival, Saturday, September 16 AND Sunday, September 17, 10am-6pm – Now in its 31st year, this is the oldest festival of its kind in the Shenandoah Valley. The festival is held at Gypsy Hill Park in Staunton and features storytellers, musicians, entertainers, vendors, food trucks, and activities. This year they are excited to partner with Waynesboro, Staunton, and Augusta County schools to have students and families share stories, traditions, and music. The festival is free to attend.
  7. Coyner Springs Kite Fly, Saturday, September 23, 10am-3pm – Tap into your inner child and go fly a kite. There will be kite demos, kite giveaways, and kite sales. Watch people try to run with a Bol Kite strapped to their back; it is hilarious and a tough workout. The family-friendly event has lots of fall activities like hayrides and pumpkin painting. The event takes place in Coyner Springs Park in Waynesboro.
  8. Grottoes Bluegrass Festival, Friday, October 6, 12pm-9pm AND Saturday, October 7, 10:30am-9pm – The festival held at Grand Caverns Park in Grottoes is so popular it is held twice a year. The festival boasts nine different artists each performing twice over the weekend. Bring a lawn chair or blanket and sit back to enjoy the tunes.
  9. Shenandoah Valley British Car Festival, Saturday, October 7, 9am-3:30pm – Now in its 41st year, this is one of the oldest car shows on the East Coast. This year’s theme is “Back to the Future.” British classic cars, British motorcycles, and British DNA and kit cars will all be displayed on the tree-lined grounds of Ridgeview Park. Get up close and personal with the cars while asking questions and taking photographs. There will be onsite food vendors and lots of door prizes. Part of the proceeds of ticket sales will benefit the Blue Ridge Area Food Bank.
  10. Fall Foliage 5K and 10K Race, Saturday, October 14, 8am – Did you enjoy the Margarita 5K in September? Come back for another Waynesboro race. This time you have the option of a 5K (3.1 miles) or 10K (6.2 miles). The course map runs through Waynesboro neighborhoods and along the South River Greenway. Runners will receive a race day t-shirt and entrance to the post-race party. After the race, check out the Fall Foliage Art Show downtown.
  11. Waynesboro Fall Foliage Art Show, Saturday, October 14, 10am-5pm AND Sunday, October 15, 12pm-5pm – The streets of downtown Waynesboro are transformed into an art gallery for the 52nd Annual Fall Foliage Art Show. The festival boasts the creative talents of 150 artisans. Attendees will see and be able to purchase paintings, printmaking, woodwork, pottery, glass, jewelry, sculpture, and mixed media. A juried exhibit titled Emerge 2023 will be hosted inside the Shenandoah Valley Art Center. The festival also features gourmet food trucks, craft beer, and live music. Spend the day or the weekend immersed in Shenandoah Valley art. Admission to the festival is free.
  12. Symphonic Poems, Saturday, October 14, 7:30pm-9:30pm AND Sunday, October 15, 3pm-5pm – The Waynesboro Symphony Orchestra kicks off its 2023-24 season with two special performances featuring guest violinist, Anton Miller. The performances will include Finlandia, Op. 26 by Sibelius, Symphonie espagnole, Op. 21 by Lalo, Tod und Verklärung, Op. 24 by Strauss, and “Les Préludes” by Liszt. Saturday’s performance will be held at the First Presbyterian Church in Staunton. Sunday’s performance will be at the First Presbyterian Church in Waynesboro. Both performances are free to attend with donations gladly accepted.
  13. Murder on the Orient Express, Thursday, October 26 through Sunday, October 29 – Visit the Wayne Theater for a live performance of Agatha Christie’s classic tale. The historic Wayne Theater opened in 1926 as a vaudeville house. It was closed for years after a fire in 1980 but then historically renovated in 2016 and reopened as a performing arts center.
  14. Waynesboro Farmers Market, every Saturday until October 28, 9am-1pm – Fresh vegetables, live music, and food trucks, oh my! Head to Constitution Park for a family-friendly morning of fun. Farmers markets are a great way to experience the local vibe of an area you are visiting.