Stinson tasting room

Photo: Stinson Vineyards

Fall in Virginia is a spectacular sight. It invites color, vibrancy and perhaps maybe even a hint of nostalgia into the air. With leaves bursting into spectacular shades and blanketing the Blue Ridge Mountain landscapes, Virginia wine country is the quintessential spot for a fall adventure. Whether you’re looking for a weekend road trip or a daytrip idea, you won’t want to miss these 6 Fall Outing Ideas in Virginia.


Apples always taste better when you pick them yourself. With local orchards like Carter Mountain Orchard in Charlottesville, Great Country Farms in Bluemont, Dickie Brothers Orchard in Roseland and Drumheller’s Orchard in Lovingston, you can pick your own peck … and bake a delicious apple pie when you’re done. Many orchards are asking for advance reservations, so be sure to call ahead.

Man picking apple in orchard


With its abundance of delicious eateries and plenty of outdoor seating, Charlottesville’s Downtown Mall, one of the longest pedestrian malls in the country, is the perfect place to spend an afternoon and enjoy the fresh fall air while you dine. You would also enjoy a day in Downtown Middleburg, known as one of the best small town experiences in America. Plus, you can enjoy shopping at unique boutiques or visiting art galleries at both. Read our comprehensive Weekend Guide to Visiting Middleburg to start planning your trip to the nation’s hunt and horse capital. 


If you love Virginia’s gorgeous fall foliage, consider leaf peeping! Choose your favorite spot and grab a camera, or simply enjoy the beauty during a hike. Try the self-guided vineyard tour at Stone Tower Winery in Leesburg, with a glass of wine in hand and a fun fact map to guide your way. Near Charlottesville, the Thomas Jefferson Trail is the perfect place to observe nature and even provides a historical overlook. The road to Carter Mountain Orchard even intersects the trail, so you can explore the stunning wooden path and visit the orchard afterwards.

Fall country roads
Truffle feast


Why wait until Thanksgiving to share a delicious meal with loved ones? Harvest season means bountiful, savory meals featuring locally sourced food and wine. One regional favorite is Barboursville Vineyards’ annual Truffle Feast.


Score some fun fall finds at a local market. Enjoy the brisk morning air at markets like the Old Town Farmers Market in Alexandria (the oldest farmers market in the country), Charlottesville City Market (voted the top farmers market in the Southeast in the American Farmland Trust’s 2019 Farmers Market Celebration) and the Farmers Market at IX, and pick up some seasonal produce, artisan jewelry or some warm freshly made food from local vendors.

Basket in a farmers market

Photo: Pippin Hill Farm & Vineyards


With harvest season upon us, it’s a great time to visit local vineyards. The weather is nice, and the wine is fresh. Make a day of it and pack a picnic for lunch. You can catch a stunning sunset at one of the picturesque locations in Virginia’s wine country. Learn more about some favorite Virginia vineyards here, and find all of your picnicking needs at our Wine & Country Shop.

Biker on a country road

Virginia offers a variety of experiences suitable for any interest. No matter which place you frequent, adventure is sure to await you. From apple picking to truffle feasts, autumn in Virginia has something for everyone. We hope you enjoy these 6 Fall Outing Ideas in Virginia, and for more local events, see our Virginia Events Calendar.  ~


Wine & Country celebrates elevated living in Virginia Wine Country. Wine & Country Life, a semi-annual life & style magazine, and Wine & Country Weddings, an annual art book celebrating elegant Virginia weddings, are complemented by the Wine & Country Shop in Ivy, VA—a beautiful lifestyle boutique that brings the pages of the magazines to life. The Shop features over 40 Virginia artisans with everything from tailgating essentials and Dubarry attire to locally made foods and award-winning Virginia wines and craft beverages for your next event. Wine & Country covers the grape-growing foothills of the Blue Ridge Mountains from Lynchburg to Leesburg, including points in between like Charlottesville and Middleburg. Ivy Life & Style Media also creates other projects, including, a collection of local resources including a popular calendar of events, family services guides and features on education, health and family day trips for parents and teachers in Charlottesville, as well as the a guide to resources for Charlottesville tourists and newcomers.