Five Ideas for a Memorable Fall Vacation in Virginia

by Patricia Keppel | Posted: Sep 25, 2018 | Updated: Sep 19, 2019

Comments: 8 Comments


Fall is truly a stunning season to visit Virginia, bringing seasonal foods, drinks, and special events that the entire family can enjoy. Plan a romantic getaway to Virginia wine, country, take the kids to a fall festival, enjoy the Great Outdoors with a hike through an iconic Virginia park…there are countless options for memorable autumn getaways, but here are five fall trip ideas that every traveler will love.


1. Solve the Corn Maze at Liberty Mills Farm in SomersetLiberty Mills Farm Corn Maze 2019

Each year, Liberty Mills Farm comes up with a new theme for their 32-acre corn maze, the largest corn maze east of the Mississippi River. The maze has four different trails, offering a variety of difficulty for all ages. After solving your chosen trail (or all four if you’re a puzzle master!), pick out the perfect pumpkin from the farm’s 8-acre pumpkin patch.

Want More Fall Fun?

Travel just down the road to Montpelier, the historic estate of fourth President of the United States James Madison and his wife Dolley, America’s “First Lady”. Take a guided tour of the home to hear about Madison’s accomplishments and struggles, then head outside to see the reconstructed enslaved community sites followed by the special exhibit “A Mere Distinction of Color”, which brings to life the powerful true stories of several individuals that were enslaved at Montpelier.

Barboursville Vineyards

Both wine and history enthusiasts alike will enjoy a stop at Barboursville Vineyards, located just across the street from the Barboursville ruins. The winery has over 25 wines available for daily tastings and offers guided tours of the winery to the public.

Continue south to Charlottesville, an historic city filled with great restaurants for the foodie travelers. Stay at the newly-opened Draftsman, a pet-friendly boutique hotel conveniently located in downtown Charlottesville.

Before heading home, stop at Carter Mountain Orchard outside of Charlottesville for their famous apple donuts and hot cider, a fitting end to your fall getaway.


2. Take in the Sights & Sounds of Southwest Virginia in Bristol, the Birthplace of Country Music

Birthplace of Country Music Museum

Bristol is known as the “Birthplace of Country Music”, hosting countless music events and live performances throughout the year, but fall combines the storied mountain music with the brilliant colors of autumn blanketing the rolling terrain. Visit the Birthplace of Country Music Museum to learn about how the legendary 1927 Bristol Sessions recordings forever changed the music industry in America.

Want More Fall Fun?

The region is also home to the Carter Family Fold, a museum and performance space dedicated to the talented country music stars. If you’re interested in learning more about the region’s musical history, continue along the Crooked Road, Virginia’s Music Heritage Trail, and take in the beautiful fall foliage as you drive through some of Virginia’s most awe-inspiring landscapes. Stop at Grayson Highlands State Park to see the wild ponies graze along the mountains, and follow the pathways up the mountain to do a section hike along the renowned Appalachian Trail. Back of the Dragon

Travel Route 16, nicknamed the Back of the Dragon, through Southwest Virginia’s prettiest mountain terrain. This scenic roadway packs 438 curves into just 32 miles of asphalt, making it a favorite route for motorcyclists and fall foliage seekers.

For even more adventure, rent ATVs at Southern Gap Outdoor Adventure and head out on the Spearhead Trails, five multi-use trail systems that afford hundreds of miles of riding through the rural mountains of Southwest Virginia.

Spend the evening at the Western Front Hotel in Saint Paul, a boutique hotel featuring a rooftop bar and an on-site restaurant that cooks up local Appalachian cuisine.


3. Experience Harvest Season in Northern Virginia’s Wine Country

Breaux Vineyards

October is the official Wine Month of Virginia, celebrating the bountiful harvest of the vineyards and the world-class products made from the grapes. Plan a trip through Loudoun and DC’s Wine Country to taste your way through some of the finest examples of Virginia wines. With over forty wineries in Loudoun County, you can create a wine-filled itinerary to suit your vacation time, whether you’re looking to fill a fall afternoon or plan a week-long trip through Northern Virginia’s bucolic wine country.

Want More Fall Fun?

Explore a few of Loudoun’s charming small towns during your visit to Northern Virginia. Downtown Leesburg has several impressive dining spots, including King Street Oyster Bar, The Wine Kitchen, and Tuscarora Mill. In Northern Virginia’s Horse Country, Middleburg affords a wide array of shopping, from small local boutique shops to upscale antique emporiums. After shopping, grab lunch at Market Salamander or the historic Red Fox Inn & Tavern, which dates to 1728.

Salamander Resort & Spa

For a luxury stay in Middleburg, book a room at Salamander Resort & Spa, a peaceful resort in the foothills of the Blue Ridge Mountains. If you’re thinking of staying closer to Leesburg, head to Lansdowne Resort & Spa, an upscale hotel in the heart of Loudoun Wine Country.


4. Hike the Picturesque Trails of Shenandoah National Park

20161010 Virginia Shenandoah Park

With 300 square miles of protected lands, Shenandoah National Park has seemingly endless trails for you to discover the beauty of the Blue Ridge Mountains. A few of the most popular hikes include Hawksbill Summit, a 2.2-mile hike that ends with a 360-degree view at the summit, Lewis Spring Falls Loop, a 3.3-mile trail that borders roaring waterfalls, and Old Rag Loop, a 9-mile classic for the more experienced hiker that offers expansive panoramic views. The park also contains 101 miles of the Appalachian Trail, allowing you to journey along one of the most famous hiking trails in the world.

Want More Fall Fun?

See Shenandoah National Park from your car as you travel along Skyline Drive, an historic 105-mile National Scenic Byway that traverses the park. The highway meanders along the mountaintops, providing exceptional views of the terrain. During the fall, the mountains are blanketed with fiery hues of yellows, reds, and oranges, coming alive with the bright autumn foliage.

Plan a few pit stops during your trip in the small towns bordering Shenandoah National Park, such as Front Royal, Luray, and Waynesboro. These hidden gems have tons of character and photo-worthy Main Streets lined with boutique shops and can’t-miss restaurants that give you a true taste of Virginia’s mountain regions.

Skyland Resort

If staying within Shenandoah National Park overnight, consider making reservations at Skyland. Situated at 3,680 feet, Skyland sits at the highest point along Skyline Drive, with incredible views of the Shenandoah Valley right outside your windows.


5. Enjoy a Quiet Coastal Vacation to Virginia Beach in the Off-Season

Virginia Beach sunset

Relax on Virginia’s shores without the crowds when you travel to Virginia Beach in the fall. While the air may be a bit cooler, the idyllic shores are still suitable for a cozy picnic, and you’ll find more affordable rates for beachfront rentals and hotels. Stroll the beaches at sunrise for a refreshing and peaceful morning walk; if you’re lucky, you may even spot some dolphins frolicking in the Atlantic waters.

Want More Fall Fun?

For a once-in-a-lifetime experience, book a horseback ride along the beach in the fall. The guided tours take you past several prime coastal landmarks, including the Virginia Beach Pier and the iconic Boardwalk.

Add a little luxury to your beachfront vacation with a stay at The Cavalier, a quintessential Virginia Beach hotel that was recently renovated. Don’t miss out on visiting the hotel’s private beach club, available only to guests and residents living in the neighborhood surrounding the hotel.


Where is your go-to fall vacation spot in Virginia? Share your trip ideas with us in the comments below!




Leave a Reply

Your email address will not be published. Required fields are marked *


Avatar Judith Moffitt says:

You made Virginia Beach in the fall sound so boring. But really it is one the best seasons in this area. The humidity is gone and that makes all the local nature trails much more fun to hike. And much to do in the surrounding cities as well.

This is what I would do for a fall vacation here.

Bike either First Landing State park or through Back Bay Wildlife Refuge to False Cape State Park. You can camp on the beach at either park.

Do a photowalk (or just a regular walk if you are not a photographer) through Back Bay and Pleasure House Point (With a finish at the Lesner Bridge to shoot the lights under the bridge.

Walk along the boardwalk at sunset or sunrise.

Go on the boat trip of a lifetime with Captain Erik Moore,, and see Nanny’s creek or the North Landing River. Be sure to go at dawn or sunset for great photos.

Check out the concerts at the Sandler Center or the Veterans United Home Loans Amphitheater at Virginia Beach (which has concerts through October). You might also find a play to catch at the Little Theater of Virginia Beach. Or hit the Comedy club or maybe attend an open mic at . Do a reading yourself where you can be anonymous.

And a visit to the aquarium is always fun. Or bring your skateboards to Mount Trashmore for a great skate park.

Take the chance to eat good ethnic food. We have Columbian, Korean, Indian, Thai, Italian, and much more. Come try something you have never tried before.

Also in easy reach by car while you are here:

Norfolk Botanical Gardens (Roses in bloom in October)
Chrysler Museum (Make sure to check out the daily glass blowing exhibition)

Or take a day for History and check out Williamsburg (They decorate for Halloweeen), Jamestown, Yorktown. Maybe even stop by Busch Gardens for Hallowscream.

Avatar Evelyn Rollins says:

what is best time to plan a trip to VA for fall foliage and wbere? We prefer mountains but have seen smokeys a lot but never been to VA. We are also interested in historical areas especially civil war battlefields or musuems. It is just my husband and mysefflf plus 2 small Yorkie dogs that always travel with us. We live in S FL and would love to spend time in cool/crisper weather with great scenary, creeks, views, and lots of history

Avatar I. H. T. says:

Great scenery in Shenandoah National Park (entry fee, of course). Winchester area has plenty of Civil War museums (and Middletown too has one big one). Belle Grove plantation has early American history and Civil War history also…a major battle there). Winchester…Plenty of battlefields… 3 major battles, about 77 battles total if you also count some lesser battles called “skirmishes”. French & Indian War history and Revolutionary War history in Winchester. History, history, history. Nicely restored and maintained historic architecture throught the heart of Winchester. Walking tours and trolley tours both. Check in first with the visitor’s center on Pleasant Valley Road. They will help you.

Avatar Gypsea says:

Peaks of Otter, when calling to reserve they can give you an idea of the best time to stay. Also it’s about 1 to 1 1/2 hours from Appomattox if you want to see the surrender site.

Avatar Judith Moffitt says:

I would do the Skyline Drive and stop at various places along the Shenandoah Valley. There are lots of battlefield areas in the valley as it was highly fought over. I would end up north at Winchester and then cross over into West Virginia to Harper’s Ferry and then again across the river to Md. To Antietam.

Avatar Sharon says:

Mid October showcases the fall colors and apple picking. There is a great orchard Dickie Brothers close to the beautiful Crabtree Falls and a swinging bridge walk with creek views. All close to the parkway access. A nice route to travel would be going towards National D Day Memorial, many other historical stops along the way, Peaks of Otter, Smith Mountain Lake State Park, Shenandoah National Park. So many wonderful areas to explore.

Avatar Alexandra Roche says:

Peak fall foliage in the mountains last year was around the beginning of November. Charlottesville is gorgeous that time of year and they have Monticello, some other presidential homes, and plenty of history in the area along with great wineries and outdoor activities. Williamsburg/Yorktown are great areas for history, and you’re also close to Norfolk and Virginia Beach which both have a ton of things to do! Lots of breweries if you’re into that.

Avatar Mike says:

I can think of two options. You can go to Bedford and hike the Peaks of Otter and then take in Poplar Forest (Thomas Jefferson’s summer home), go to nearby Appomattox and even consider the D-Day memorial. Or go to the Shenandoah Valley. Hike Hawksbill, take in Montpellier where James Madison wrote the Constitution and go to New Market battlefield. You can’t wrong with either!