6 Summer Road Trips

A guy, a great car and a plan to hit a handful of destinations from the white sand beaches of Chincoteague to the windswept peaks of the Cumberland Mountains.

Photo by Jennifer Chase

Astronauts returning from space often remark that the experience has made them more appreciative of their home planet, and even though I’ve never flown higher than the average 737 can go, I get it. Any sort of far-flung travel has the same effect on me—it’s exciting to visit other places, but nothing looks as good as Virginia coming into view as I round that last bend and realize I’m home again. 

There’s a lot to explore here, too. Our incredible diversity of geography and culture might surprise even some natives. Consider this—the Old Dominion stretches from Assateague Island National Seashore in the Atlantic Ocean to Cumberland Gap National Historical Park, which lies further west than Detroit. 

The idea of experiencing as much of Virginia’s amazing scenery as possible this summer sparked an idea—why not drive a lap of the state and discover some roads less taken? So I did. 

Loading my family of five into an Audi Q7, we started near our home in Northern Virginia and traveled to the Eastern Shore, across Southside on Route 58, motoring west past Marion and heading north through Hot Springs, the Shenandoah Valley and then across to Middleburg. We tasted our first clam fritter sandwich and rode in a Formula 1-style racecar, buzzed over rock and through river via RTV, and listened as chamber music filled a mountain valley. And there was more. At the end of it all—seven days and more than 1,100 miles later—pulling into our driveway in the dusk of a muggy June evening, I felt that familiar contentment wash over me. Only this time, I didn’t need to leave Virginia to get it.

Do it all at once like we did, or take it one road trip at a time. But definitely go. The road is waiting. 


Where rockets fly and ponies swim.

The Route: From Virginia Beach, northeast on Route 13, 104 miles.

Virginia is increasingly a technology hub, and rocket-maker Orbital ATK in Dulles and NASA’s Wallops Flight Facility on the Eastern Shore combine to make the sleepy seaside village on Chincoteague Island an ideal destination. 

Picking up Route 13 in Virginia Beach, we take the Chesapeake Bay Bridge Tunnel (it costs $12 to cross, but only $5 to come back). Near the southern tip of the Eastern Shore is Kiptopeke State Park in Cape Charles, where we find a nice beach on the bay with very fine sand. We make a mental note to swing through here again and rent one of their three-bedroom cabins or huge six-bedroom lodges in a secluded area where kids can roam.

But we are pressing onward, which means a lunch stop in Exmore, to sample The Exmore Diner’s renowned fresh-caught local seafood. The classic diner’s t-shirts read, “Old fashion food at old fashion prices,” which is exactly what we find. The day’s catch is listed on a whiteboard—the clam fritter sandwich is a home run on the day of our visit. If the time is right, the diner serves unique drum fish ribs, which are very popular.

On our way to the Marina Bay Hotel & Suites, our home for the night, we pass the 1932 art deco Central High School building in Accomack County, which is currently for sale and which would make an incredible property when restored to its previous glory. But we don’t linger, in a hurry to get to the main event of our visit—the rocket launch.

When we get to the hotel, Hannah at the reception desk points out that the launch site, across the water on Wallops Island, is directly visible from the hotel’s private dock where guests can tie up their boats. 

Listening to the launch countdown online from the dock, the rocket ignites on schedule, a brilliant white flare in the pre-dawn darkness. More than 30 seconds later, its seismic rumble reaches us, arriving in ripples, like pulsating thunder.

Alternatively, we could have watched from Wallops Visitors Center, which is right on Route 175, the road to Chincoteague. You can’t miss it: it’s the building with a couple of old rockets displayed outside. Another good vantage point is at Chincoteague Island Waterman’s Memorial Park at the southern tip of the island. (This is what we’d have done if the launch was not at 4:44 a.m., timed when the International Space Station was scheduled to zoom overhead in orbit as the target of the Orbital Cygnus supply ship atop the Antares rocket.) All three viewing points are located within 10 miles of the launch pad.

Rockets launch from Wallops on average 5-6 times a year, depending on mission schedules. The nextone is slated for Nov. 10. Findout more by calling the WallopsVisitors Center.


The smart and stylish 76-room Marina Bay is only a year old and not only has a modern-looking breakfast area and lounge, but also has its own boat landing and slips on the dock. The hotel’s clean, fresh design is beachy without being kitschy. Special kudos for having clever room clocks that show the time on three sides, so they are readable from both beds in a double room. $150-$500 per night.


Mister Whippy ice cream is also open in the morning as the Lil’ Whippy coffee and doughnut shop. The cake-style doughnuts hit the spot after the hard work of cheering an early morning rocket launch.


Chincoteague is famous as the home of Misty, the horse in the children’s novel, and for its annual pony swim from Assateague National Seashore. The swim took place this year July 25. National park passes are valid.

The Eastern Shore Railway Museum in Parksley displays cars from the golden era of rail travel, including a Pullman sleeper car and a couple of cabooses.

The white sand recreational beach at Chincoteague National Wildlife Refuge is ideal for sunbathing. Parking and restrooms are available at the end of Beach Access Road, and lifeguards are on duty all summer. Entrance fee is $20 per car and passes are valid for one week.


The driving experience.

The Route: From Norfolk, west on Route 58, 163 miles.

Having returned from the Eastern Shore, we head west on Route 58 in search of race cars. Stretching the full width of the Commonwealth, Route 58 covers 511 miles from the sands of Virginia Beach to the mountainous Cumberland Gap, passing along the way the “bullrings” that helped give rise to Nascar. 

Those include small circuits like South Boston Speedway, and bigger ones like Martinsville Speedway and Bristol Motor Speedway (which someone thoughtlessly located on the Tennessee side of Bristol). It also includes Virginia International Raceway, a mighty European-style road racing circuit on the banks of the Dan River, which has earned acclaim as the site of Car and Driver magazine’s Lightning Lap sports car test, the U.S. equivalent of Germany’s Nürburgring.

Reaching Clarksville on the shores of Kerr Reservoir, we stop in at Los Bandidos Mexican Restaurant, a pair of state police patrol cars in the parking lot providing all the local endorsement we need. We are not disappointed—the Chilaquiles Mexicanos dish is an absolute winner. 

We were lured to the South Boston area by the flowing, pastoral 1,300-acre, 3.3-mile European-style road racing resort VIR and its new Formula Experiences, which offers the opportunity to ride along in an open-cockpit sports racer like the ones we’ve seen racing in the 24 Hours of Le Mans—either as a passenger riding with an expert racer or even as a driver yourself. It was our chance to pull on a fire suit and strap on a helmet, just like pro racers do on television. 

Proximity to VIR and the South Boston Speedway make Berry Hill Resort & Conference Center a perfect place to stay. Providing the best of the old South and modern travel, the stunning white Greek Revival home began as a more modest structure in 1728 before being remodeled into its current form in the 1830s. Today, guests stay in a new hotel constructed behind the antebellum Berry Hill mansion. 

Before calling it a night, we stop in at Berry Hill’s snug Darby’sTavern pub for a casual bite and a drink after the excitement of our day of racing.


The historic Berry Hill antebellum mansion is backed by a contemporary 92-room hotel with a restaurant and tavern—and the 70-foot-wide portico is a gorgeous place to relax in the rocking chairs and watch the lightning bugs emerge on the expansive front lawn. While the rooms provide all the expected modern amenities, including some with balconies overlooking the Virginia countryside, the twin Jefferson and Lafayette “Mansionettes” that flank the circular driveway convey traditional Virginia style. Also of note, you don’t have a mansion the age of Berry Hill without it accumulating some ghost stories—if you ask Rick, one of the property’s maintenance men, he’ll say, “You don’t find the ghosts, the ghosts find you.” $130-$195 per night. 


Check out the IMSA WeatherTech SportsCar Championship at Virginia International Raceway Aug. 17-19, the only mid-Atlantic stop for the premier North American sports car racing series.


Formula Experiences also offers a night ride. That means sitting shoulder-to-shoulder with the driver while tearing through the dark at 140 mph.


Stargazing and splendid nature.

The Route: From South Boston, west on Route 58, 107 miles.

Continuing west on Route 58, we head for luxury mountain resort Primland. On the way, we go through Danville, passing its Millionaires Row of mansions, which offer some of the region’s best examples of Victorian and Edwardian domestic architecture, and Martinsville, where the Smithsonian’s Virginia Museum of Natural History features life-size cast skeletons of dinosaurs that once roamed here. 

This is where we tune in to WDVA AM 1250 to listen to the Marketplace show, with callers selling car wheels and clothing in the fashion of a pre-Craigslist, over-the-air era, as they’ve done for generations in rural Virginia.

Arriving at Primland, it doesn’t take long to discern its fabulousity—it truly is difficult to overstate. The sprawling estate offers a variety of activities, including the opportunity to helicopter back to Virginia International Raceway to drive zoomy Audi sports cars on the track with Danish nine-time Le Mans race champion Tom Kristensen.

But today, we opt for a slightly less dynamic motorized activity, crawling through the woods on two-person Polaris RZR recreational terrain vehicles (RTVs). The “Razors” have an astonishingly smooth and surefooted ride on trails that would have a Jeep bouncing uncomfortably. 

We chug along behind our guide Carlton (who also leads guests in upland wingshooting and driven pheasant shoots), accompanied by the “thuuub” of the Polaris’ engine. The route—a mere sampling of the resort’s more than 90 miles of trails—encompasses an amazing variety of soil, from loamy black mud to slick red river clay to the iridescent oyster-shell gleam of mica embedded in the rocks all around. 

Back at the lodge, Primland features its own astronomical observatory, which hosts what they call starwalking every night (weather permitting). We couldn’t check on the progress of the Cygnus spacecraft whose launch we’d witnessed days earlier, but we did look at the moon, Jupiter and globular nebula through the resort’s powerful Celestron CGE Pro 1400 telescope with the help of staff astronomer Lauren Peery. Primland’s altitude means there is no ambient light in the night sky, giving the view of celestial objects here a rare clarity. 


The 12,000-acre resort in Patrick County features a cedar and stone 26-room lodge, the two-story Pinnacles suite and the over-the-top Golden Eagle Treehouse—a sleek and well-appointed aerie suspended over the Dan River Gorge. Here, the stunning mountain landscape is visible from every corner of the property. The experience includes golf, spa, sport shooting and gourmet dining. The chef will even prepare any game you bag. $340-$1,080 per night.


The resort also has a smaller Celestron telescope located in the Great Hall. Guests may arrange to use it privately on the terrace to see stars that are not quite as far away.


Try Mountain Biking on the resort’s 6-mile section of the old Appalachian Trail, which ran through the property from 1936 to 1948.

Choose from three Sporting Clays courses open year-round.

The Bow and BB-Gun Shooting Range is designed to appeal to the 18 and under set.  


The best of town and country.

The Route: From Meadows of Dan, west on Route 58 to Route 16 north, 90 miles.

Setting our sights on the General Francis Marion Hotel, we resume our westward path on Route 58. 

As amazing as the rest of the Commonwealth is, the incredible abundance of natural wonders and activities available in this segment of our drive are by far the most extensive.

We learn that in Galax, the fire department carnival hosts lawn mower racing—though we miss it, we mark it down as a must-do on our next visit. 

Detouring to Cumberland Gap, the westernmost extent of Virginia, we press further on Route 58.

Along the way, we admire the beauty in Grayson Highlands State Park and the Mount Rogers National Recreation Area, which features the highest point in Virginia at 5,728 feet. Then there’s the Virginia Creeper Trail, the 34-mile rails-to-trails mountain biking and hiking path from Abingdon to Damascus. There are bike ferries to provide for one-way riders and canoe liveries for paddling in the Holston River.

Cumberland Gap National Historical Park straddles the state line with Kentucky. We park on the Virginia side and hike the Lewis Hollow Trail toward Skylight Cave. (The park’s caves are off-limits now because of White-Nose Syndrome that is killing bats at an astonishingly rapid rate.) Wildflowers are a highlight of this relatively easy 1.2-mile hike.

The impressive Pinnacle Overlook is a couple of miles hike from the cave, though it is also accessible by car from the Kentucky side, where the visitor’s center is located. The 2.4-mile road to the overlook would make an excellent training hill for road bicyclists because of the light, slow-moving automotive traffic.

From there, we head back east to Marion to spend the night in the historic Roaring ’20s-era General Francis Marion Hotel, named after the Revolutionary War hero who inspired Mel Gibson’s fictionalized character in The Patriot, as was the town itself. On the recommendation of co-owner Joe Ellis, we enjoy dinner at The Speakeasy restaurant, seated on the balcony overlooking Main Street.

We balance the display of nature at its most awesome and powerful in this region with the town’s many arts offerings. 

Marion’s stunning 1929 Lincoln Theatre is only a few doors down the street from the hotel. It features a hybrid design blending art deco and Mayan revival styles, harking to its opening as a cinema. Today, it is a venue for live performances. (There are plans to add a cinematic-grade movie screen to fill the lovely venue’s seats more frequently.) We buy handmade soap to take home with us from the theater’s gift shop, Lola’s.

It should come as no surprise that a community with the spirit to create and support gems like the General Francis Marion Hotel and the Lincoln Theatre also has the resources to come together and create recreational activities for families. That’s why they built the Park Place Drive-In movie theater, putt-putt golf, batting cage and video arcade that sits just off Main Street.


The prohibition-era General Francis Marion Hotel delivers on its promise of “Southern hospitality at its finest,” serving as the anchor of Marion’s fun and quaint downtown. The Card Room is the most unique public area, with card-themed floor tiles hinting to its speakeasy history. $120-$190 per night.


Sisters Café & Gifts in the old Piggly Wiggly supermarket building serves what we declare to be the world’s best blueberry-pomegranate smoothie.


Our Audi Q7 features a built-in LTE Wi-Fi hot spot, which proves crucial for attention-challenged rear seat occupants and their personal devices. 


Mountain roads and music.

The Route: From Marion, north on Route 16 to Tazewell, then northeast to Route 220, 190 miles.

Seeking a scenic northeastern course, we head for Garth Newel Music Center in Hot Springs by way of Route 16. 

Dubbed the Back of the Dragon, the route winds its way through 32 miles and 438 curves to Tazewell. Along the way is Hungry Mother State Park, where there is fishing, boating and more than 17 miles of hiking and biking trails.

We pass the 4,710-foot peak of Garden Mountain and enjoy the view from the nearby 3,500-foot overlook before arriving at the Back of the Dragon welcome center in Tazewell. The center’s co-owner Danny Addison is a local insurance agent when he’s not promoting visits to the snaking highway where he rides his Indian motorcycle and co-owner Larry Davidson rides a Triumph.

“The Back of the Dragon is the only place you can read your own back license plate coming into the turn while you are going out of it,” Addison boasts. Back of the Dragon is part of a network of similarly twisty nearby roads dubbed Claw of the Dragon, comprising more than 350 miles of Virginia’s best motorcycle and sports car roads. The Audi Q7is excellent in addressing these curves, by the way, even loadedwith a family of five and a week’s worth of luggage.

Just east of here lies Burke’s Garden, an amazing geographical feature resembling a volcanic crater. (It was actually created when subterranean limestone caverns collapsed.) 

The upland valley, nicknamed “God’s Thumbprint,” was George Vanderbilt’s first choice when seeking a location for the Biltmore Estate, but he was unsuccessful in convincing local landowners to sell, so he moved on to set his sights on Asheville, North Carolina.

The tiny town of Bland is also nearby, and a visit to the high school’s baseball field there could reveal the skin left from my knee in the vicinity of home plate during an away game in 1983. (I was safe, and we won the game.) 

There are more than enough great roads as we continue on our journey northward to Covington. Just a short distance up Route 220 delivers us to Falling Spring Falls, a lovely feature that was documented by Thomas Jefferson in a 1781 visit to Augusta County.

We arrive a while later in Hot Springs at the Garth Newel Music Center (the name means “New Home” in Welsh), home of the nation’s only year-round piano quartet chamber music experience. Additionally, the site hosts visiting musicians for concerts in the 200-seat Herter Hall—once an indoor training ring for Arabian horses, according to director Shawn Puller.

If the notion of classical music being played in Appalachia seems incongruous, don’t worry—you aren’t the only one to think that. “It is a horrible idea to do it here, but it wouldn’t work anywhere else,” laughs Puller.

That’s because the verdant pastures and hills that surround the property provide a kind of enforced tranquility. “There’s no better place for chamber music,” Puller adds.

We stay in the Stradavari Suite in the Manor House, enjoying the roomy bedroom, beautiful hardwood floors and a help-yourself commercial grade kitchen where we fixed breakfast the next morning from the abundant supplies provided.

For dinner, we visit the nearby Warm Springs Inn, which has a German-themed tavern. The newly-added pretzel bun burger proves to be the best item on the menu, especially when followed by the signature apple strudel and the chance to watch the sunlight fade from the rocking chairs on the front porch.


Where else can you enjoy a piano quartet house band playing classical music among the tree frogs and crickets of a pastoral 114-acre Virginia mountain venue? Garth Newel provides a musical experience unavailable anywhere else along with unmatched serenity and fabulous Manor House rooms and standalone cottages for overnight stays after the show. $120-$250 per night.


The Milk House Market, just down the road from Garth Newel, will pack picnic lunches made from locally produced ingredients. Your best bet is the Jackson sandwich—turkey, cheese, arugula and pepper jelly on a croissant—a menu standout.


A Way With Words asks listeners to call with questions about regional phrases such as “bless your heart,” while the hosts debate word origins and etymologies. Favorite episode: “Naked As A Jaybird.”

Hosted by four historians, Backstory applies the lessons of the past to current events and culture. Favorite episode: “Are We There Yet? Americans On Vacation.”

Aaron Mahnke’s Lore explores non-fiction scary stories and folklore, including the witch-trial of Grace Sherwood near Lynnhaven. Favorite episode: “Dead End.”

The Tiny Desk Concerts from NPR music invite musicians to perform in-studio, representing a range of styles, from contemporary Cuban roots music to Appalachian folk songs. Favorite episode: “Anna & Elizabeth.”

With Good Reason is hosted by Charlottesville native Sarah McConnell, who explores a range of topics from animal science to art with experts. Favorite episode: “Moving Pictures.”


In good taste.

The Route: From Hot Springs, north on Route 220, 210 miles.

To reach our destination—the Red Fox Inn in Middleburg—we chart a course northward on Route 220 and then turn eastward on route 250 toward Staunton. 

Along the way, we stop in McDowell for a visit to Sugar Tree Country Store for some of Highland County’s fabulous maple syrup, direct from the source. (You can save the trip by ordering online, says owner Glenn Heatwole.)

We turn north on Route 11 so we can visit Route 11 Potato Chips in Mount Jackson before we arrive in Winchester, Virginia’s apple production capital and home of the Apple Blossom Festival each May. Winchester has many fine things to recommend it, but the city’s incredible Handley Library is truly unique and worth visiting. The library’s architecture is stunning, and the city has been a responsible steward of the 1913 Beaux-Arts facility, even as the building has been modernized and expanded over its century of operation. The copper-domed library is a must-see, and is also home to a collection of books on the history of the Shenandoah Valley that can’t be found anywhere else.

Winchester is blessed with an embarrassment of riches when it comes to restaurants, cafés and breweries, but the Cork Street Tavern is the original member of the downtown’s renaissance and always merits a stop.

From Winchester, the Red Fox Inn lies only 30 miles east, on Route 50, which provides a scenic rolling tour of the Old Dominion’s horse country and Upperville, the site of the oldest horse show in the country.

Once in Middleburg, we check in at the historic inn, which Jacqueline Kennedy Onassis once called “the coziest, most enchanting house in Virginia.” Who are we to argue with Jackie’s judgement on such matters?

While there, we enjoy the fabulous Belmont Suite. The 1728 inn has outgrown its original building, so they have added nearby houses to a campus that they call “The Stray Fox Inn,” with the Belmont Suite serving as its flagship.

Dinner in the Red Fox’s tavern is tremendous. Traditional Virginia peanut soup seems mandatory when enjoying a historic establishment such as this. It may be exclusive, but the vibe here is warm. We hear the Tavern’s hostess greeting regulars at breakfast, asking one gentleman, “Here for your coffee this morning, Mr. Cramer?”

Middleburg is full of excellent restaurants. We especially appreciate the homey Side Saddle Café, where the menus are handwritten, the waitress informs you that “Mom made the pound cake this morning,” and the walls bear autographs from visiting service members.

The National Sporting Library & Museum is another must-visit spot here, featuring the region’s deep history of country pursuits.

Not far away on Route 28 is the Smithsonian Air and Space Museum’s Udvar-Hazy Center near Dulles Airport. This is the facility where they exhibit planes too large for the D.C. museum, which means Virginia is home to the space shuttle Discovery, an SR-71 Blackbird spy plane and a Concorde SST supersonic airliner, among others.

David Delagarza


This Middleburg institution, dating to 1728, has unmatched heritage and atmosphere, especially in the downstairs tavern serving meals and drinks. Stay in the inn itself or on its campus in one of the suites at the Stray Fox Inn. Whichever you choose, take time to close your eyes and soak up the atmosphere. $225-$425 per night.


Support Middleburg’s furry population by stopping in for a cone or a dish at Scruffy’s Ice Cream Parlor, which is run by the local animal shelter as a fundraiser.


Fast Car, Tracy Chapman
Hazel Woods, Andy Jenkins
Little Red Corvette, Prince
Everything is Love, The Carters
Born to be Wild, Steppenwolf 
Life is a Highway, Tom Cochrane 
Take it Easy, The Eagles
I’ve Been Everywhere, Johnny Cash
Hit the Road Jack, Ray Charles 
Truckin’, Grateful Dead 

This article originally appeared in our August 2018 issue.

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