Virginia cities and towns show off when falls color shows up. Seasonal flavors grace restaurant menus while festivals held in and around downtown areas celebrate all there is to love about autumn. We’ve put together a list of the top towns and destinations for experiencing an unforgettable fall in Virginia. Use this guide to get your fill of autumn-inspired foods, drinks, and acticities.
Photo Credit: Eric Kelley
The Charlottesville area is the home of the University of Virginia Cavaliers, Monticello, Ash-Lawn Highland, a plethora of wineries, and a growing craft beer scene. Close to the southern entrance of Shenandoah National Park in the foothills of the Blue Ridge Mountains, Charlottesville offers extraordinary leaf peeping opportunities around every corner.
Eat: Citizen Burger Bar | The Whiskey Jar | Ace Biscuit & Barbecue| Bizou| Public Fish & Oyster | C & O | The Local
Stay: Boar’s Head | Quirk Hotel Charlottesville | Graduate Charlottesville | The Draftsman
Play: Monticello Wine Trail | Saunders-Monticello Trail | Monticello Country Ballooning | Carter Mountain Orchard
SALEM & ROANOKE
Photo Credit: Carey Harveycutter
Salem and Roanoke are beautiful gems that teeter-totter between the southern Shenandoah Valley and the northern Blue Ridge Highlands. Tucked between the Blue Ridge Parkway and Allegheny Mountains, Roanoke offers plenty of outdoor recreation and amazing views. With over 400 miles of mountain biking trails in and around Roanoke, you’ll find new trails to conquer every time you visit.
Eat: Blue Apron (Salem) | Local Roots (Roanoke) | The River and Rail (Roanoke)
Stay: King George Inn B&B (Roanoke) | Hotel Roanoke
Play: Virginia’s Blue Ridge Cheers Trail| Dixie Caverns (Salem) | Roanoke Valley Greenways
Blacksburg is home to the Virginia Tech Hokies and it’s a sweet little mountain town (one of the best, according to Blue Ridge Country) tucked into Virginia’s Blue Ridge Highlands. The town is part of the New River Valley and has a myriad of outdoor recreation experiences, from cycling and hiking to rock climbing and paddle boarding on the New River.
Eat: The Cellar Restaurant | Cabo Fish Taco | The Blacksburg Tavern
Stay: The Inn at Virginia Tech Skelton Center | Main Street Inn | Clay Corner Inn
Play: Huckleberry Trail | The Lyric | Brush Mountain Wilderness | Beliveau Estate Winery
South Boston boasts beautiful views and outdoor recreation with three rivers: the Dan, the Staunton and the Banister, collectively, Southern Virginia Wild Blueway. Paddle along foliage-lined shores, of which 80 miles of the 100+ are designated Virginia Scenic River.
Eat: Southern Plenty Cafe | Molasses Grill
Stay: Charles Bass House | Oak Grove Plantation B&B | Berry Hill Resort
Play: The Prizery | Southern Virginia Botanical Gardens | Shangrila Horseback Riding
WILLIAMSBURG & YORKTOWN
Williamsburg and Yorktown are two points of the Historic Triangle. The third is Jamestown. In 1607, Jamestown was the site of the first English-speaking settlement. Williamsburg was the first Virginia capital, and Yorktown is where America claimed Revolutionary War victory.
Eat: Yorktown Pub | Two Drummers Smokehouse | Le Yaca| Blue Talon Bistro| Fat Canary
Stay: York River Inn B&B | The Williamsburg Lodge | Kingsmill Resort
Play – Colonial Parkway | Colonial Williamsburg | Golf at Kingsmill Resort | Busch Gardens Williamsburg
Photo Credit: The Vacation Channel, @vacationchannels
Newport News is minutes from America’s historic beginnings. Get to know this gem bounded by the James River and Hampton Roads harbor. Livability.com called Newport News one of the “Top 100 Best Places to Live,” so for sure it’s also a great place to visit.
Eat: Al Fresco Ristorante | Fin | Schlesinger’s Steaks
Stay: Marriott at City Center | Hilton Garden Inn
Play: Huntington Park | The Mariners’ Museum & Park | Endview Plantation | Virginia Living Museum
Culpeper is a beautiful destination at the crossroads of Routes 15, 29 and 522. Visit for yourself to see why Virginia Living magazine called Culpeper “One of Virginia’s Friendliest Towns.” In the fall, Graves Mountain Lodge (located outside of Culpeper) hosts their annual Harvest Apple Festival, a can’t-miss event for those that truly love everything autumn.
Eat: Flavor on Main | Grass Rootes | It’s About Thyme
Stay: Thyme Inn | Suites at 249 | Waldon Hall
Play: Old House Vineyards | Stillhouse Distillery at Belmont Farm |
Photo Credit: Brad Deel, @brad.deel
Norton is another great destination for outdoor recreation. Just climb to to the top of Flag Rock for a 1,000′ view down into the city! The vantage point is absolutely perfect for foliage photography, as panoramic views allow you to take in both Virginia and Kentucky mountain scenery.
Eat: Snack Shack | Fishtales Family Restaurant | The Wood Booger Grill | Sugar Hill Cidery
Stay: Days Inn
Play: Sugar Maple Bicycle Trail | Powell Valley Overlook | Country Cabin | High Knob Recreation Area and Lookout Tower
Photo Credit: Adam Lewis, @adamtlewis
Wachapreague is right around the mid-way point of Virginia’s Eastern Shore, on the Atlantic Ocean side, but protected by barrier islands. The pace of life is slow and the wildlife is majestic. Fall is a migratory season and the birds love the Shore as a stopover point.
Eat: Wachapreague Island House Restaurant
Stay: Teasers Fisherman’s Lodge | Wachapreague Inn
Play: Foxy Lady Charters | Daytrippers
Deltaville Tap & Raw Bar, Photo Credit: Latisha Boone
Middlesex County is a great place to enjoy the bounty of the Chesapeake Bay. Bring your appetite for seafood and beautiful water views when you venture this way.
Eat: Merroir (Topping) | The Table at Wilton (Deltaville) | Deltaville Tap & Raw Bar (Deltaville)
Stay: Ivy Cottage on the Piankatank River (Hartfield) | The Dockside Inn (Deltaville) | The Chesapeake Inn (Urbanna)
Play: Norton’s Sailboat Charters | Piankatank River Golf Club | Urbanna Oyster Festival in November
Photo Credit: Steven Morris
Coined DC’s Wine Country, Loudoun County must have the greatest number of wineries of any Virginia county. At last count, there were more than 40!
Eat: Clyde’s Willow Creek Farm (Broadlands) | Grandale Restaurant (Purcellville) | The Restaurant at Patowmack Farm (Lovettsville)
Stay: Goodstone Inn (Middleburg) | Lansdowne Resort (Leesburg) | Salamander Resort (Middleburg)
Play: Catoctin Creek Distilling Company (Purcellville) | DC’s Wine Country
MORE TO LOVE
Alexandria— Located on the Potomac River within eyesight of Washington, D.C., Alexandria is a stunning Virginia destination, especially in the fall. Take a walk through Old Town Alexandria, founded in 1749, and enjoy the preserved 18th and 19th century architecture of the residences, the picturesque cobblestone streets, and the boutique shops and restaurants that line the street. Follow King Street all the way to the waterfront and catch a glimpse of the nation’s capital across the scenic river.
Giles County — Giles is the home of Mountain Lake Lodge, the filming site of the beloved Dirty Dancing, starring Patrick Swayze and Jennifer Grey.
Staunton — National Trust for Historic Preservation calls Staunton “One of a Dozen Distinctive Destinations in the United States.”
downtown staunton, Photo Credit: Jeff Bramwell
Fredericksburg — Stroll through history and great boutique shopping where George Washington’s boyhood home is just a stone’s throw across the river.
Nelson County — From “The Walton’s” and the Appalachian Trail to craft beer, wine, and orchards, Nelson County is a fun place for fall.
Richmond — In case you’ve missed what travel resource Frommer’s has said about Richmond … “While you weren’t looking, Richmond got cool.” Visit and see for yourself why it’s a top destination for fall.
Photo Credit: Adam Lewis, @adamtlewis
Damascus — This outdoor paradise has one of America’s rails-to-trails gems — the Virginia Creeper Trail. Bring your bike or rent one for a leisurely ride through the foliage.
Front Royal — If you enjoy fall’s beauty from the water, head to the Canoe Capital of Virginia and paddle the Shenandoah River.
Dickenson County — Home to the “Grand Canyon of the South,” the Russell Fork River, which divides Pine Mountain to create the largest canyon east of the Mississippi.
Breaks Interstate Park, Photo Credit: Cathy Anderson, @cathyandersonphoto
Harrisonburg — Virginia’s first Culinary District is found in downtown Harrisonburg. Discover something tasty while enjoying the colors of fall.
Massanutten — Situated between the Alleghenies and Shenandoah National Park is Massanutten Mountain, home of Massanutten Resort.
Danville — Danville is called the “Last Capital of the Confederacy” as Confederate President Jefferson Davis occupied a bedroom at Sutherlin Mansion for a week prior to Confederate surrender at Appomattox.
Floyd — Home of the most photographed site on the Blue Ridge Parkway — Mabry Mill.
Mabry Mill, Photo Credit: Beverly Smith
Woodstock — Recognized by the Arbor Day Foundation as a Tree City USA, you can count on fall’s colors to really shine in Woodstock.
Virginia Beach — Virginia Beach has 38 miles of shoreline, 28 miles of public beaches, and three miles of one of America’s best boardwalks, as proclaimed by Travel + Leisure, National Geographic, Budget Travel, and others.
Pleasure House Oysters: Chef’s Table Tour, Virginia Beach
Reedville — An historic 1860s fishing village, Reedville was actually the wealthiest town per capita in the U.S. into the early 1900s thanks to its commercial fishing industry.
Shenandoah National Park — Encompassing nearly 198,000 acres, SNP has four entrances into it via Skyline Drive. Pick one (or all!) of the 75 overlooks for a beautiful photo opp.
Shenandoah Valley — “The Big Valley,” “The Great Valley,” “The Breadbasket of the Confederacy,” … the Shenandoah Valley has been known by many names. I just call it home.
Which part of Virginia is your favorite for fall weekends? Leave a comment and let your voice be heard!
J. D. Cave
The ‘Cabin Capital of Virginia’ , Luray-Page County, boasts over 400 unique cabins which provide an amazing experience Lots to see and do or just relax on the porch/deck. See ShenandoahWoods.com.