Virginia Road Trips:

If you’re like me and get all kinds of excited at the mere idea of a road trip, then you know the pure joy that can be had taking the wheel to get to a destination. Virginia’s southeastern corner, known widely as Hampton Roads and more locally as the 757, offers a myriad of starting points in traveling by road. However, the mere point of a road trip doesn’t have to be ending up at a set destination. The road traveled in of itself can be an excellent reason to get out there and see what Virginia has around the next bend.

Here are five roads that begin or travel through Hampton Roads that you can fulfill your wanderlust on:

1.) U.S. Route 17:

US 17 enters Virginia running from the coastal plain city of Chesapeake and ending in the Shenandoah Valley at Winchester, Virginia. While there is plenty along the route to see and do, If you begin your travels in Yorktown, stop by Yorktown Beach to take in the boardwalk there. Meander through historic Yorktown by foot. Colonial National Historical Park is here as well and it is a great opportunity to explore the historical significance of nearby Yorktown Battlefield. Mobjack Bay Coffee Roasters and Petite Cafe, located on Main Street, makes excellent sandwiches paired with your choice of coffee, beer and wine.

Another excellent option for a tasty meal is right over the Coleman Bridge in Gloucester at Scoot’s BBQ. Having won the title before for “Best BBQ restaurant in Virginia, it also has excellent crab cakes and sides. My personal favorites are the cucumber salad and signature baked beans.

Continue up Route 17 to see the beauty of rural eastern Virginia along the Chesapeake Bay. Tappahanock has a Main Street that is bustling and full of coastal charm as its namesake river flows close by. Visit the NN Burger for a juicy bite to eat. The restaurant for 10 years in a row has been ranked, “Best in Virginia” by Virginia Living magazine. With live music, specialty “freak” shakes and a dog-friendly atmosphere, the iconic state theme of LOVE in Virginia also has its largest mural painted here for an excellent photo-op.

2.) State Route 5:

Deemed an official “Virginia Byway”, it is a short drive at 55 miles. Running between Williamsburg and Richmond, it is famous for the The Virginia Capital Trail, a bike and walking trail which spans all but 3 miles of Route 5. As you start in Williamsburg, head down to Spoke + Art Provisions Co., a cafe and pit stop for bicyclists making their commute. Serving light fare featuring local artists’ work for sale, it is a relaxed atmosphere that starts you on a good note.

Travel up the winding road to take in historical sites. One cool stop is Westover Church in Charles City County, sitting on a nice bluff along Herring Creek. Constructed in 1730, this site has played a prominent role in American history, and its grounds are peaceful.

As you see the crest of the marvelous Richmond skyline at the end of the route, take a jaunt along the Riverfront Canal Walk, where numerous entertainment opportunities await. Give Bottoms Up Pizza in historic Shokoe Bottom a try while you are there to take in all of the sights. A 1st place winner of “Best Pizzeria” by Virginia Living in 2023, the eclectic menu features plenty of signature pizza dishes, such as their Chesapeake and Goat in the Garden. They also have an extensive beer and spirits menu to enjoy with your meal.

3.) U.S. Route 58:

Running the entire southern length of Virginia and for the briefest mile into Tennesseee, this 508-mile road begins right on the Virginia Beach oceanfront and ends right outside of Cumberland Gap National Historical Park. A route that takes at least a long weekend to fully appreciate, one can break it up into easier chunks for sure.

It begins to get a bit more scenic as you enter into Clarksville, as the town sits along the largest lake in the state. Enjoy a brew at Buggs Island Brewing, which has sweeping views of its namesake lake. Along with having a tasty selection of craft beers, their menu has a winner in its version of a po boy sandwich made with catfish. Between the towns of Stuart and Meadows of Dan, the route takes a sudden climb up into the mountains, where at the top one can visit the famed Lover’s Leap. From this point on, Route 58 has some truly breathtaking vistas to behold.

For those who are into the great outdoors, you have lots of options along 58 from four state parks directly on the route, as well as a national forest and recreational area. Grayson Highlands State Park is a true marvel, which has sweeping vistas. The park is known for ponies that roam wild within its parameters. Mount Rogers National Recreational Area is a particularly lovely section of 58, as you wind through thick forests and along clear mountain streams.

If you see the road all the way to its end in Tennessee, check out the quaint, laid-back Gap Creek Coffee House and Cafe in Cumberland Gap. Its college town-vibe serves up excellent frappachinos and hearty sandwiches. Bonus: For even more variation, US Route 58 Alternative in Western Virginia goes a bit more to the north than its counterpart, offering 87 miles of mountainous charm. If celebrating Bigfoot is your thing, the city of Norton has its ode to the legendary creature with its own statue on the gorgeous Flag Rock Recreation Area. Nearby, Wood Booger Grill serves up American fare with a big dose of fun in the spirit of Bigfoot. Jefferson National Forest stretches its glorious majesty through the town. The High Knob Observation Tower within the forest provides lovely views a hundred miles in all directions.

4.) Colonial Parkway:

A 24-mile stretch of road that stretches between Yorktown and Williamsburg, this beautiful drive is sandwiched between the York and James Rivers. Contained within Colonial National Historical Park, the byway connects Yorktown Battlefield with Historic Jamestown.

As you stroll along the bluffs of Yorktown, visit Indian Field to relax on the sand or beachcomb. Colonial Williamsburg is right in the middle of the parkway, so you have lots of dining and leisure choices there. Stop by Duke of Gloucester street to grab a coffee and pastry at Aroma’s. While you’re there, one can absorb the colonial history in a walkable, picturesque area. The College of William and Mary, founded in 1693, is also here and is the second oldest university in the United States. Continue on down the parkway, where you see it to its end in Jamestown. Billsburg Brewery is here right by the James City County Marina. One of the most visually pleasing spots of any brewery in the area with more than a dozen craft brews to choose from, the sprawling grounds offer a multitude of lounge areas, food trucks and sometimes live music. As a bonus, one could catch a ferry a half mile away from the parkway’s end across the James to Surry County and continue the adventure.

5.) US Route 60:

A 300-plus mile route, you can get both the ocean and the mountains covered with this road. Starting in Virginia Beach and reaching the West Virginia border in Allegheny County, Route 60 has many beautiful stops to behold. Whether one would prefer an urban vibe, a more natural setting or a mix of the two, this road has you covered. In Virginia Beach, First Landing State Park is a unique experience that contains a maritime forest, rich cypress grove swamps and a near pristine beach to comb. You will have spectacular views of the Chesapeake Bay crossing the Lesnar Bridge, and is a great alternative to the often traffic-jammed, heavy construction that is I-64 if you’re looking to cross the Hampton Roads Bridge Tunnel (it is part of the interstate when you cross over into Hampton). Route 60 runs through neighboring Norfolk through the Oceanview section of the city, where you have plenty of places to grab a bite.

Driving north into Newport News, you can visit the Noland Trail, an urban oasis that is 5 miles long, heavily forested and nestled along expansive views of the James River. Subway Station is an old-school sandwich shop beloved by locals and college students at nearby Christopher Newport University that is close by if you get hungry after your hike.

Although punctuated with many bustling urban sections, Route 60 gets very scenic and picturesque north of Richmond. A two-lane highway in some parts as it rises in elevation, the road can be at times very rural and lacking in conveniences, so make sure you have a full tank of gas.

James River State Park in Gladstone is worth checking out. A designated International Dark Sky Park, skywatchers of all levels of interest can behold the wonder of the celestial skies here. From here, you have opportunity to experience the wonderous natural beauty that is the Blue Ridge Mountains. Photo-worthy stops are plentiful from Rockfish Gap on northwestward.

Lexington is a mountain town worth exploring, and it has two noteworthy colleges steeped in history: Washington and Lee University and Virginia Military Institute. A good pit stop isSweet Treats Bakery for custom coffee and their signature cakes if you are sight-seeing in town.

Road trips in Virginia, starting right in the 757 region, give plenty of compelling reasons to explore the diverse geography Virginia has to offer by car. Here’s to these adventure-filled roads (more) or less traveled !