30 Favorite Fall Towns & Destinations

by Casey Higgins | Posted: Sep 19, 2014 | Updated: Apr 17, 2018

Comments: 28 Comments


Virginia cities and towns show off when falls color shows up. Seasonal flavors grace downtown menus while festivals celebrate the harvest, too.

We asked our Facebook followers which Virginia destinations they love most during the autumn season and their picks are included here. Chime in with your favorite by posting a comment!



Scenic Farm in the Charlottesville area. Photo by John Hulburt.

Photo by John Hulburt

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.

– Eat – Citizen Burger Bar | The Whiskey Jar | Ace Biscuit & Barbecue

– Stay – 200 South Street Inn | Omni Charlottesville | The Dinsmore House Inn

– Play – Monticello Wine Trail | Saunders-Monticello Trail | Monticello Country Ballooning

“There is nothing more fun that when my husband and I grab our friends, jump in the car, hit all of the wineries, taste, buy, have dinner and end up at Burnley Vineyard …” – Karen G.

“I love driving along Rt. 231 between Charlottesville and Madison, a beautiful winding road with lots of farms.” – Melissa M.

“Love the mountains and vineyards!” – Sally W.

“… Sitting outside at any of the vineyards enjoying great wine and breathtaking views.” – Nevin H.

“… Beauty, history, vineyards, great food and really nice people!” – Shirley H.




Downtown Salem

Downtown Salem

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, you’ll enjoy plenty of outdoor recreation and amazing views. In July 2014 Roanoke was acknowledged by USAToday.com as one of the “Ten Best Cities for Biking.”

– Eat – Blue Apron (Salem) | Local Roots (Roanoke) | The River and Rail (Roanoke)

– Stay – Brugh’s Inn of Salem | King George Inn B&B (Roanoke) | Hotel Roanoke

– Play – Virginia’s Blue Ridge Beerway | Dixie Caverns (Salem) | Roanoke Valley Greenways

“Just got back from Salem … home away from home (Germany). We love the area, close to [the] Appalachian Trail, Carvins Cove, horses, hiking, fishing and so many more outdoor activities! We got to meet deer, snakes and black bears and most important an awesome kind of people – our friends! And one day, we are going to live there for good! Just love it! ‘Cause Virginia is for Lovers!” – Carmen M.

“Roanoke I love, but pretty much would enjoy the entire state.” – Connie G.





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. In fact, Outside Magazine included Blacksburg as a “Top Ten Dream Town for Outdoor Enthusiasts” in 2001.

– Eat – The Cellar Restaurant  |  Cabo Fish Taco  |  Blacksburg Taphouse

– 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 Harvest Festival

South Boston Harvest Festival. Photo by David Hungate.

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 – Bistro 1888   |  Southern Plenty Cafe

– Stay – Charles Bass House  |  Oak Grove Plantation B&B  |  Berry Hill Resort

– Play – The Prizery  |   Southern Virginia Botanical Gardens  |  Shangrila Horseback Riding





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 | Berret’s Seafood (Williamsburg)  Two Drummers Smokehouse (Williamsburg)

– Stay –  York River Inn B&B (Yorktown) | The Williamsburg Lodge | Liberty Rose Inn (Williamsburg)

– Play – Alliance Tall Ship Day Sails | Colonial Parkway | Colonial Williamsburg

“Colonial Parkway is charming and then Howl-O-Scream in the evening. So fun!” – Laura M.

“… Driving along the Colonial Parkway and opening the windows and smelling the salt marsh and looking at all of the leaves changing colors …” – Bonnie P.

“I even have a favorite tree in Williamsburg.” – Donna R.

“Yorktown and the amazing views of the Coleman Bridge, the ships, and gorgeous walkway and sunsets!” – Terri C.

“Williamsburg! Crisp and gorgeous!” -Kimberly M.



James River Bridge

The James River Bridge from Newport News.

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 – Green House  |  Al Fresco Ristorante  |  Fin

– Stay – Marriott at City Center  |  Hilton Garden Inn

– Play – Huntington Park  |  The Mariners’ Museum & Park  |  Endview Plantation



Culpeper is a beautiful destination at the crossroads of Routes 15, 29 and 522. Visit for yourself to see why earlier this year Virginia Living magazine called Culpeper “One of Virginia’s Friendliest Towns.”

– Eat – Foti’s Restaurant  | Flavor on Main  |  Thyme Market

– Stay – Thyme Inn  |  Suites at 249  |  Hazel River Inn Bed and Breakfast

– Play – Old House Vineyards  |  Stillhouse Distillery at Belmont Farm

“Culpeper, Virginia is a beautiful town full of festivities and the Main Street is always decorated for each season and holiday. Next door to Culpeper is the Graves Mountain Lodge where the ‘Harvest Apple Fest’ is held. I never miss this event!” – Tracy C.


—– NORTON —–

Flag Rock Recreation Area

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

– Stay – Holiday Inn

– Play – Sugar Maple Bicycle Trail  |  Powell Valley Overlook  |  VA-KY Opry  |  Country Cabin



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

“Rte 13 … my visit to my grandma’s house on the Eastern Shore (Jenkins Bridge). I remember crossing the Chesapeake on a ferry … love the Eastern Shore … the wild horses … untouched land …” -Rhonda D.



Norton Sailing School. Photo by Mark Atkinson.

Norton’s Sailboat Charters. Photo by Mark Atkinson.

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) |  Something Different Restaurant (Urbanna)

– Stay – Camelot on the Piankatank River (Hartfield)  |  James Ross River Plantation (Urbanna)  | The Chesapeake Inn (Urbanna)

– Play – Norton’s Sailboat Charters  |  Piankatank River Golf Club  | Urbanna Oyster Festival in November



Breaux Vineyards. Photo by Steven Morris.

Breaux Vineyards. Photo by 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

“Loudoun County … for the wineries, farm tour in Oct., restaurants, views … also Bluemont Winery and Great Country Farms right across from it.” – Barbara R.



Giles County — Giles is the home of Mountain Lake Lodge, the filming site of the beloved Dirty Dancing, starring Patrick Swayze and Jennifer Grey.    “Giles County. I love the mountains and everything about Virginia.” – Clayford E.

Staunton National Trust for Historic Preservation calls Staunton “One of a Dozen Distinctive Destinations in the United States.”    “Staunton. You can see it all from there!” – Richard R.

Downtown Staunton

Downtown Staunton

Fredericksburg — Stroll through history and great boutique shopping where George Washington’s boyhood home is just a stone’s throw across the river.    “Fredericksburg downtown because [it] is full of festivities and the Main Street is always decorated for every holiday. It’s beautiful.” -Yilena I.

Nelson County From “The Walton’s” and the Appalachian Trail to craft beer, wine, and orchards, Nelson County is a fun place for fall.    “Got to hit wine country in Nelson County!” – Gary L.    “Crabtree Falls … the drive through the Blue Ridge Mountains is absolutely one to remember. Amazing sunrises and sunsets.” – Anttravese S.

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 2014.    “I like visiting Richmond in the fall, it’s so pretty and the temps are comfortable. I like hiking in Shenandoah before the crowds. come.” -Filiz R. 

Monument Avenue, Richmond. Photo by John Henley.

Monument Avenue, Richmond. Photo by John Henley.

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.    “I live in Damascus … We plan a drive to a new destination every weekend. A day trip and we can go to White Top, The Breaks, Grindstone, Bear Tree, Backbone, Hungry Mother and so on.” -Susan P.

Front Royal If you enjoy fall’s beauty from the water, head to the Canoe Capital of Virginia and paddle the Shenandoah River.    “Front Royal. Always beautiful and close to the Shennandoa [sic].” -Sally R.

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 is breathtaking in the fall with all the mountain views of the awesome fall foliage at the many overlooks.” – Marsha W.

Breaks Interstate Park

Breaks Interstate Park

Harrisonburg Virginia’s first Culinary District is found in downtown Harrisonburg. Discover something tasty while enjoying the colors of fall.    “Harrisonburg, Virginia! Stay in town for the dining and fun fall festivals and drive up to the Swift Run Gap entrance to Skyline Drive …” – Anna B.

Massanutten Situated between the Alleghenies and Shenandoah National Park is Massanutten Mountain, home of Massanutten Resort.    “Massanutten Resort! Perfect location to enjoy Shenandoah National Park … zip lines, chairlift rides …” -Sarah E.

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.    “Danville … peaceful place … moved here from New York … just love Virginia.” -Sassee L.

Millionaire's Row

Millionaire’s Row in Danville. Photo by David Hungate.

Floyd Home of the most photographed site on the Blue Ridge Parkway — Mabry Mill.    “Floyd, VA and apple picking.” – Liz B.

Woodstock — Recognized by the Arbor Day Foundation as a Tree City USA, you can count on fall’s colors to really shine in Woodstock.    “Woodstock Virginia. Most quaint little town with sweet people and beautiful mountains to hike or just sit and look at.” – Karen H.

Virginia Beach — Virginia Beach as 38 miles of shoreline, 28 miles of public beaches, and three miles of one of America’s best boardwalks, as proclaimed by Travel + LeisureNational GeographicBudget Travel, and others.    “I always liked the Cape Henry Lights … the beach is secluded enough that you can chase crab around, have a picnic, read, have your own little private view, all just minutes from the strip.” – Jason A.

Pleasure House Oysters, Chef's Table Tour

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.
“There’s not a bad view, not a bad sunset, not a bad anything in this waterside community. I love the view from the Crazy Crab, and their fried green tomatoes are awesome!” – Leigh H.

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.    “Just love Shenandoah National Park in general. Love those mountains.” -Holly D.

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.    “Shenandoah Valley: The winding roads with cider stands and harvest season goodies and crafts and of course the changing of the leaves.” – Rhoda F.

[Tweet “”… it was weird seeing mountains for the first time … I can’t seem to leave!” – M.K. #LOVEVA”]

  Which part of Virginia is your favorite for fall weekends? Leave a comment and let your voice be heard!


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MWCAdam DunfordJohn lambertL ScherrGinger Griffin Recent comment authors
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Carter Mt. many memories of apple picking w/my young son yrs ago, every fall season

Adam Dunford

Mabry Mill is in Meadows of Dan VA not Floyd!!!

John lambert

US 220 S from Monterey to Hot Springs with dinner at Warm Springs at the B&B on Grist mill Square and drinks at the Sam Sneed Tavern in Hot Springs.

L Scherr
L Scherr

Clarksville is also a beautiful place in the fall. The leaves changing along the lake line is amazing!