We all love a good vacation. And while it’s nice to hop on a plane and jet off to a tropical beach or go on a European cities tour, that’s not always in the cards. A road trip can be a fun, affordable way to get out there and see something you’ve never seen before – or take the time to see a lot more of your favorite things. Road trips can be something as simple as a weekend away or it can be a whole week of theme-based exploring. It’s always a good time to start planning your next road trip with family, friends, or maybe even just with your camera and a good book (or two. Or ten). Start brainstorming for your next on-the-road adventure with these eight ideas for the best road trips in Virginia.

1. Music Lovers Road Trip: The Crooked Road – Virginia’s Heritage Music Trail
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If you love music, this one’s for you. The Crooked Road is a 300-mile journey along U.S. Route 58 through the heart of the Appalachian Mountains to see and hear some of the best performers of traditional country, folk and bluegrass music anywhere in the world. Beginning in the Blue Ridge and continuing down to Franklin County, your trip takes you to major music venues, including the Birthplace of Country Music in Bristol, Blue Ridge Music Center and the Old Fiddlers’ Convention and Rex Theater in Galax, The Carter Family Fold in Hiltons, The Floyd Country Store (home of the Friday Night Jamboree) in Floyd, and the Ralph Stanley Museum in Clintwood – and that’s just to name a few. Festivals and special events can be found almost year-round, along with countless other wayside attractions. Visit artisans and instrument makers along the way and discover the music that has shaped Virginia’s history. Click here to learn more about this epic trip.
2. Get In Touch With Your Southern Roots: The James River Plantations
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Route 5 from Richmond to Yorktown may only cover 63 miles, but it spans centuries. Follow the path of the James River through stunning farmlands from the city’s capital to the site of the first permanent British colony in the United States. Start in Richmond with its wealth historical museums, homes and businesses that paint a picture of life before and during and after the Civil War. Then head east out of the city to find thousands of acres of stunning farmlands and beautifully restored plantations and historical homes around nearly every bend. Sites include Sherwood Forest (home of President John Tyler), Berkeley Plantation (site of the first Thanksgiving and birthplace of President William Henry Harrison), Shirley Plantation, Evelynton (site of Civil War battles and home of Edmund Ruffin who fired the first shot of the Civil War at Fort Sumter) and Westover Plantation (built by Richmond’s founder, James Byrd). End your tour by going through Colonial Williamsburg, Yorktown and Jamestown to see where the nation got its start. Learn more about the plantations and this trip here.
3. Beach Bums and Ocean Lovers Road Trip: Virginia Beach, Chesapeake and The Eastern Shore
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Few things in the world are better than a beach and Virginia Beach is one of the best. The beach holds a Guinness World’s Record for the longest stretch of pleasure beach anywhere. With 35 miles of coastline to explore, it’s impossible to be bored. Boardwalks,, festivals and beautiful beachfront are the perfect way to start this road trip. From Virginia Beach, head east on the 18-mile Chesapeake Bay Bridge-Tunnel to the Eastern Shore of Virginia. Full of undisturbed wildlife and pristine beach habitat, the Eastern Shore is Virginia’s gem. Heading north on Route 13, you’ll find stops such as Kiptopeke State Park in Charles City, not to mention Charles City itself, a quaint town with specialty and antique shops, as well as it’s own historical sites. Follow the route up to Onancock (considered one of the best small towns in Virginia) and take a ferry to Tangier Island, a small oyster and fishing community that has retained its original old English accent for centuries. And of course, your trip wouldn’t be complete without a visit to Assoteague and Chincoteague Islands. Time it right in the summer, and you can witness the centuries old Pony Swim, as the Assoteague Island wild ponies swim to Chincoteague for a festival and fundraising auction. And whatever you do, please, please be sure to enjoy the amazing oysters, fish and other seafood that make this region one-of-a-kind.
4. The Road Trip For People Who Hate Driving: Take a Train
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If you want to get out and see Virginia, but your daily commute has utterly destroyed your desire to be in a car – try a train car instead. Virginia by Rail offers Amtrak tours starting in Manassas (Prince William County) and ending in Norfolk. Along the way, you’ll make stops in Fredericksburg and Richmond, with ample time to get out and explore incredible sites. In Manassas, visit the Manassas Museum and Ben Lomond Historic Site (featuring an historic home used as a Civil War hospital, graffiti left by Civil War soldiers and slave quarters). At the next stop, explore Occoquan, a quaint, 18th century riverfront town. In Fredericksburg, visit the Fredericksburg Museum and Cultural Center, take trolley tours and see the James Monroe Museum and Hugh Mercer’s Apothecary Shop (founded pre-Revolutionary War). From there, you’ll head to Richmond where parks, battlefields, historic homes, cemeteries and a wealth of museums are waiting to be discovered. Finally, arrive in Norfolk to see the Naval Station Norfolk, the Chrysler Museum of Art and the Norfolk Botanical Gardens. Or, check out the city by sea aboard the American Rover or Spirit of Norfolk. This is a trip that just can’t go wrong. All you have to do is sit back, relax and wait for the next stop. Here are some Virginia day trips you can take by train!

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5. Presidential Homes Tour: See why Virginia is the “birthplace of presidents”
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As you well know, Virginia is home to more presidents than any other state: seven, to be exact. Fortunately, many of the homes of these great men are still available to us today. Starting at Mount Vernon, just south of Washington, D.C., George Washington’s historic home gives a glimpse into life as it would have been in his heyday with working farms, house and grounds tours, museums and living history exhibits. A few hours south on the Northern Neck (Westmoreland County), you can see where Washington was born on the family farm founded by his great-grandfather in the 1600s. He only lived there a short time, but his boyhood home, Ferry Farm near Fredericksburg is not far away. The James Monroe Museum, on land once owned by the former president, is also in Fredericksburg and has the nation’s largest collection of memorabilia related to Monroe’s life and presidency. Head south towards Richmond and stop at Berkeley Plantation (William Henry Harrison’s birthplace) and Sherwood Forest (estate of John Tyler), both along the James River, and learn how these neighboring 9th and 10th Presidents got their start. Just outside of Richmond sits Tuckahoe Plantation, Thomas Jefferson’s boyhood home. As you head west, visit Jefferson’s retreat at Poplar Forest outside of Lynchburg before arriving in Charlottesville to visit his "crown jewel", Monticello. Not far from Monticello is Ashland-Highlands, the historic home and estate of James Monroe. Another hour or so west will take you to James Madison’s Montpelier. Mountain views and the James Madison Museum make this well worth the stop. Finally, your tour ends in Staunton off of I-64 West at the birthplace of Woodrow Wilson. Tour his birthplace and be sure to visit the Woodrow Wilson Presidential Library to learn about his early life and eventual presidency.
6. Great Outdoors Road Trip: Hiking and Camping along Skyline Drive
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Pack your tent, lace up your boots and hit the trails for a cheap road trip with priceless views. The Skyline Drive, beginning in Front Royal, is only 105 miles through the Shenandoah National Park, but the stops along the way can make it last for days. In addition to 75 scenic overlooks, the drive offers access to hikes like Compton Peak, Hogback Mountain, Big Meadows, Hawksbill, Rose River Loop and Doyle’s River Falls. Visit the National Park Service website at www.nps.gov to learn more about camping and backcountry camping permits available in the Shenandoah National Park, then get ready to take a hike. Get more info about this epic adventure here.
7. Hit the Wine Trails: You'll want to go easy on the driving for this one, but it will be so worth the trip!
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We would love to give you a simple trip idea: go here, then go there. But with more than 230 wineries across the state, how can we pick? Best to leave that up to you, and so we'll just say: pick a region, designate your driver, and get tasting. To get you started, here are a few wine trails worth the trip: Route 211 in Northwest Virginia offers seven wineries, a distillery and gorgeous scenery start to finish. Chesapeake Bay Wine Trail has nine wineries and historical stops along the way. For added incentive, a "passport" provides discounts on wine after the first seven stamps. Fauquier Wine Trail near Warrenton could keep you busy for months with 23 wineries and vineyards. Nearby, the Loudoun Wine Trail is all about boutique perfection, complementing gorgeous wines with amazing dining. In Central Virginia, the Monticello Wine Trail achieves Jefferson’s dream of a nation of drunks… wait... we mean his dream of making Virginia wines to rival those of Old World Europe. Yeah, that. Mission accomplished, sir. 30 wineries broken up into Northern, Eastern, Southern and Western trails create some of the Commonwealth’s best vintages. Richmond stays in the game with a Heart of Virginia Wine Trail featuring a $20 passport ticket that includes a glass, a trail map and tasting at all 6 wineries along the way. And there are more…so many more. If this is your idea of an ideal weekend getaway, check out VirginiaWine.org.
8. Shenandoah Valley: “The Perfect Three-Day Roadtrip” – and we quote
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The Huffington Post recently called the Shenandoah Valley "The Perfect Three-Day Road Trip Through Virginia." We really can’t argue. Whether you take three days or three weeks, there’s no shortage of sights, sounds, and experiences in this amazing part of the state. Starting in Staunton, then passing through Natural Bridge, Lexington, Hot Springs, and then ending in Roanoke, there’s hardly a better way to see and experience some of the most beautiful sites Virginia has to offer. Get some history and culture along the way with the Frontier Culture Museum, Woodrow Wilson Presidential Library and Museum, the American Shakespeare Center, Virginia Military Institute and Museum and Humpback Bridge, as well as battlefields and historical markers at every stop. Pamper yourself at the Homestead Resort or historic Hotel Roanoke. Entertain the kids (or adults who act like kids) with outrageous roadside attractions like Dinosaurland, Natural Bridge and the Virginia Safari Park. Visit the Roanoke Star or meander through the Farmer’s Market. And enjoy incredible food along every part of the journey with fine-dining and or eclectic roadside treats. We hate to seem unoriginal, but the Shenandoah Valley has so much to offer and there’s no time like the present to get out there and take advantage of it. If you need a little more convincing, here are 19 reasons you should do this one.

We kinda have a desperate need for travel right about now. The best part about writing for Only In Your State is discovering for ourselves all of the amazing things that Virginia has to offer! Many of them have been right under our noses for years and we just didn’t know. How many of these trips have you taken? Tell us about your favorite road trip ideas, and should you happen to take one of these, we want to know all about it!

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Best Road Trips in Virgina

Tori Jane | October 26, 2021

What are some must-visit attractions in Virginia?  

Virginia is grossly underrated, if you ask us! It’s a place that’s particularly rewarding for two groups: history buffs and nature enthusiasts. And if you’re both, well, that’s just peachy! Visit colonial Williamsburg for a glimpse into our nation’s past, where plenty of the 18th-century buildings are still standing. It was the capital of Virginia from 1705 until well past the Revolution. Of course, those with an interest in US history (or just the nation in general) should definitely visit Arlington National Cemetery, where several former US Presidents have been laid to rest, as well as prominent historical figures and military folk. Mount Vernon, George Washington’s home from 1754 until his death 45 years later, is also an absolute must-see. If you’re an art lover (and even if you’re not, honestly), you should check out the Virginia Museum of Fine Arts, in Richmond.  

Where are some beautiful places to visit in Virginia? 

We saved the must-see natural wonders for this paragraph! Virginia is a breathtaking state, and there are plenty of natural wonders that cannot be missed. The Natural Bridge of Virginia is an incredible historic area that towers more than 200 feet high and 90 feet in length. It’s exactly what it sounds like – a natural bridge – and it’s a part of the National Register of Historic Places. It became a state park in 2014. Also worth checking out is Shenandoah National Park, which is home to some of the best hiking in the entire state – if not the country! Virginia Beach is another natural must-see. This beach is among the most popular in the country, though, so plan accordingly – there does tend to be crowds. The Luray Caverns are an incredible experience that must be lived to be fully understood, and there’s also the incredible wonder of Great Falls Park. For more of our favorite must-see wonders in Virginia, check this list out.  

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