Fall in Waynesboro comes with a packed calendar. Festivals, live music, art, food, and plenty of reasons to get out and enjoy the season are all coming up. Grab your calendar and start making plans because there’s a lot happening around here this October!

Apple Days Arts & Crafts Show – Willow Oak Plaza, October 3 from 10-5pm & October 4 from 12-4pm

Head to Willow Oak Plaza Saturday, October 3rd and Sunday, October 4th for Waynesboro’s annual Apple Days Festival. Be sure to get famous apple turnovers and a bushel of apples from a local orchard while browsing homemade jewelry, local artisan items, crafts, and treats.

Shenandoah Valley British Car Club Annual Car Show – Ridgeview Park, October 3 starting at 8am

One of the oldest car shows on the East Coast, the SVBCC British Car Festival remains a favorite car gathering in the Shenandoah Valley! Cars of all conditions are encouraged to be displayed. Festivities begin with donuts and coffee on Saturday, October 3rd among the massive trees and lovely views of Ridgeview Park in Waynesboro. British Classics, British Motorcycles, as well as British DNA Kit Cars are welcome! There will be an on-site food vendor, prizes, car displays, and a wandering band of pipers!

Wine Over Waynesboro – Sunset Park, October 3 from 4-7:30pm

Join The City of Waynesboro Parks and Recreation for a fun day of live music, local wine, food, and a beautiful place to watch the sunset! Bring a picnic blanket or lawn chair and find the perfect spot to hang out or to have your picnic. There will be 7 wineries offering two wine tasting each for $20 with a souvenir Wine Over Waynesboro tasting glass included. Each individual winery will also sell bottles and glasses of wine. Sooners BBQ food truck will be there as well.

Well-behaved, leashed dogs are welcome at this event.

Sunset Park will be open to the public during this event.

Carpooling is encouraged as parking is limited at Sunset Park. There will be overflow parking areas and a shuttle.

Live Music Lineup
4:00pm to 5:30pm Liz Barnes and Barbara Martin
6:00pm to 7:30pm Queen City Porch Swingers

In partnership with Common Wealth Crush

Fall Foliage 5k/10K – Constitution Park, October 10 starting at 8am

Start your day with a run before the Fall Foliage Art Show! Saturday, October 10th, take a brisk fall run through the charming neighborhoods of Waynesboro, Virginia and along the South River Greenway. Take in the beauty of fall along the South River with the smell of crisp, fall leaves under your feet. The Fall Foliage 5K/10K includes a race day t-shirt, fully stocked aid stations, and a post-race party with food and drink. There is still time to register, prices go up after October 7.

Fall Foliage Art Show – Downtown Waynesboro, October 10 & 11 from 10am – 5pm


Join Shenandoah Valley Art Center for the 55th annual Waynesboro Fall Foliage Art Show! On Saturday and Sunday, October 10th & 11th, 160 fine artists will fill the streets of historic downtown Waynesboro. Spend a gorgeous fall weekend celebrating the arts in the Shenandoah Valley! Collaborate on the community art project, view creative work from painters, potters, jewelers, sculptors, carvers, and weavers, enjoy local craft beer, live music, and so much more. No admission fee, and plenty of free parking.

Holiday Kick Off and Small Business Saturday at Winterfest!

November 28th, details coming soon!