We may be biased, but fall in Virginia is pretty magical. From the Blue Ridge Mountains to the Chesapeake Bay, when the leaves start changing, it’s hard to stay indoors. Luckily, there are many activities that are best enjoyed in the crisp Virginia air.

Apple Picking

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 in 2020 so please call ahead.

Annual Virginia Festivals

Besides the impending holiday season, there is much to celebrate in the fall. Check out the virtual Virginia Film Festival in Charlottesville or the Middleburg Film Fest (virtual and in-person), attend one of the several Oyster Festivals across the state, or enjoy a beer at any Oktoberfest celebration.

Charlottesville’s Downtown Mall

With its abundance of delicious eateries and plenty of outdoor seating, the 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. Plus, you can enjoy shopping at unique boutiques or visiting art galleries.

Photo by Jennifer Jones

Outdoor Excursions

In between summer vacations and the holidays, it can be nice to steal a quick weekend excursion with friends and family, and Virginia offers plenty of outdoor fun. Go for a trip on the James River or visit a vineyard for a horseback ride through the fields with a tour company like the Indian Summer Guide Service.

Photo by Aaron Watson Photography

Harvest Dinners & Seasonal Feasts

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

Virginia Horse Racing Events

Virginia’s horse races offer something exciting for all ages. This year you can tailgate at home and cheer on the horses while watching the virtual stream of The Foxfield Races, The International Gold Cup or the Montpelier Hunt Races.

Leaf Peeping

Capture the most beautiful part of the season as the leaves change colors. According to the Virginia Department of Forestry’s fall foliage reports, we are in peak leaf-peeping season. Go for a bike ride through the mountains, or coast down Skyline Drive to stop at an overlook and take in the scenery. The Shenandoah National Park offers plenty of local hikes and trails for all skill levels to soak in the rich colors.

Photo by Jennifer Jones

Local Markets

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) and Charlottesville City Market (voted the top farmers market in the Southeast in the American Farmland Trust’s 2019 Farmers Market Celebration), and pick up some seasonal produce, artisan jewelry or some warm freshly made food from local vendors.

UVA Football Games

Fall means tailgating season. Take your corn hole set to the backyard as you stream the game and cheer on the Cavaliers. There are plenty of local restaurants, breweries and boutiques that offer all your tailgating essentials this season with to-go boxes, such as the Wine & Country Shop. Just don’t forget your orange and blue!

Photography: Sera Petras Photography | Styling: Marisa Vrooman of Orpha Events | Venue: Alumni Hall, UVA | Catering: The Local | Desserts: Kilwins & Paradox Pastry | Beverages: The Bitty Bar, Valley Road Vineyards & Bold Rock Cider | Rentals: Orpha Events & Charlottesville Wine & Country Shop| Florals: Tourterelle Floral Design | Sunglasses: Primary Eyecare | Jewelry: Andrew Minton Jewelers | Makeup and Hair Styling: A More Beautiful You | Transportation: Mercedes-Benz of Charlottesville

Virginia Vineyard Outings & Picnics

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.

Photos: Rachel May Photography | Venue: Barboursville Vineyards | Clothing: Verdigris & Brooks Brothers | Ring: Ana Cavalheiro Fine Jewelry | Hair: Brianna B. Adams | Makeup: Gohar Makeup | Female Model: Noelle S., Modelogic | Male Model: Patrick K., Modelogic

No matter how you choose to celebrate, fall is the perfect season to explore our beautiful state. From apples to oysters and horses to ‘Hoos, autumn in Virginia has something for everyone. ~


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 CharlottesvilleFamily.com, 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 CharlottesvilleWelcomeBook.com a guide to resources for Charlottesville tourists and newcomers.

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