Eat, Drink, Love: Ultimate Fall Itineraries for Exploring Virginia
While there's no bad time to visit Virginia, fall offers an abundance of delights beyond the stunning foliage. October marks Virginia Wine Month, with harvests of oysters, apples, cider, pumpkins, and more. On Oct. 19, Virginia Harvest Parties pop up statewide—from vineyards and restaurants to scenic beaches.
Celebrate the 50th anniversary of the iconic Virginia is for Lovers slogan (since 1969) with our eat, drink, love guide. These three itineraries turn a long weekend into a flavorful adventure, blending culinary experiences with active pursuits to keep your energy high.
Wining, Dining, and Gallery-Hopping in Richmond
Richmond, Virginia's capital and site of Patrick Henry's famous 'Give me liberty or give me death' speech, now leads revolutions in design, food, and arts. Praised by Travel + Leisure and National Geographic, it's a vibrant city base for exploring nearby wineries.
Virginia excels in viognier, an Old World white grape thriving here. Several top wineries lie within an hour's drive.
Wining
Thirty minutes southeast, Upper Shirley Vineyards overlooks the James River. Enjoy house wines at the restaurant, vineyard horseback or bike tours, and live music. Visit on Oct. 11 for Rockin' Under the Stars, pairing tunes with wine, beer, and food.
Forty-five minutes southwest in Powhatan, Skippers Creek Vineyard specializes in viognier amid 5 acres of vines. Nearby Bodie Vineyards offers simple red and white varietals. For variety, attend the Powhatan Wine Festival on Oct. 5, featuring 25 regional wineries.
End in Richmond's Scott's Addition for ciders from Blue Bee, Buskey, and Courthouse Creek, showcasing Virginia's apple harvest.
Dining
Bon Appétit dubbed Richmond “America’s Next Great Restaurant-Obsessed Town.” Try Alewife, with seafood chops by chef Lee Gregory (formerly of The Roosevelt), named among GQ's best new restaurants of 2019.
Longoven, No. 3 on Bon Appétit's 2019 list, offers artful tasting menus. Highlights include porcini ice cream paired with flourless chocolate cake.
Art
Travel + Leisure calls Richmond a potential top art destination. The Institute for Contemporary Art at VCU opens the Great Force exhibit on Oct. 5, featuring artists like Pope.L and Sable Elyse Smith.
The Virginia Museum of Fine Arts presents an Edward Hopper exhibit on Oct. 26 (65 works on hotels/motels) and Kehinde Wiley's Rumors of War statue, arriving post-NYC debut.
Where to Stay
The Jefferson Hotel blends historic luxury with opulent details like bronze alligator statues. For modern style, Graduate Hotel honors Arthur Ashe with tennis ball art.
Brews, Biking, and Country Music Roots: Roanoke to Bristol
A scenic two-hour drive from Roanoke to Bristol—birthplace of country music—winds through Appalachian towns, breweries, and trails.
Breweries
Over 20 breweries dot the route along I-81, including Roanoke's Big Lick and Bristol's Bristol Station Brews. Highlights: Blacksburg's Bull & Bones, Christiansburg's Sinkland Farms, and Abingdon's Wolf Hills.
Biking
Known as the East Coast's Mountain Bike Capital, Roanoke offers trails for all levels. Beginners love the Roanoke River Greenway; experts tackle Dragon's Back. Rentals from Roanoke Mountain Adventures or UnderDog Bikes.
Refuel at Smith Mountain Lake's chili festival (Nov. 2).
Country Music Heritage
Bristol's State Street straddles VA-TN. Visit the Birthplace of Country Music Museum (Smithsonian affiliate) for 1927 Bristol Sessions lore. Explore the Crooked Road trail, featured in Ken Burns' Country Music.
Where to Stay
Bristol Hotel offers mountain views and history. In Roanoke, historic Hotel Roanoke (Hilton Curio Collection) dates to 1882.
Oysters, Pork, and Peanuts Along Virginia's Coast
Norfolk, at the Virginia Oyster Trail and Salty Southern Route intersection, is perfect for savory adventures.
Oysters
Nearby Virginia Beach's Pleasure House Oyster farm revives the Lynnhaven variety. Tours include chef's tables in the river, supporting conservation.
Pre-Thanksgiving Oyster & South Festival at Greenbrier Farms offers shucked oysters and pumpkin picking.
Pork and Peanuts
Smithfield, pork capital, features Darden’s Country Store's farm-fresh hams and peanuts. Suffolk, Peanut Capital, boasts Planters history and Mr. Peanut statue.
Festivals
Neon Festival (Oct. 17-18) illuminates Norfolk with art and food trucks. Fall Town Point Virginia Wine Festival (Oct. 19-20) pairs 30+ wineries with music and eats.
Where to Stay
Hilton Norfolk The Main overlooks the Elizabeth River. Intimate Four Eleven York Street offers boutique charm and dining.
Plan Your Trip
Visit the official Virginia tourism website for more fall ideas and request this free travel guide to start your adventure.
