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Explore the Best Scenic Drives Virginia Has to Offer: A Road-Tripper's Guide from Charlottesville

Explore the Best Scenic Drives Virginia Has to Offer: A Road-Tripper's Guide from Charlottesville

Discover Virginia’s top scenic drives to see the state’s spectacular mountains, wineries, farms, and historic sites. In this guide, we reveal the essential routes like the Blue Ridge Parkway and Skyline Drive, ensuring you’ll experience the best visuals and cultural spots on your scenic drives around Central Virginia without wading through unnecessary information.

Key Takeaways

  • Virginia’s scenic drives include over 2,500 miles of byways, blending natural beauty with rich history, offering something for nature lovers, history enthusiasts, and explorers alike.
  • The Blue Ridge Parkway and Skyline Drive offer breathtaking views and cultural experiences with spots like Humpback Rocks and Shenandoah National Park, providing a glimpse into mountain life and wildlife.
  • Lesser known routes like Route 231 or Route 22, connect you to iconic historic towns and delivering the state’s most beautiful bucolic farm & estate roots.
  • We suggest a fun car with great windows - don't have one? We have a Jeep Wrangler with soft top or Chevrolet Tahoe w/ panoramic sunroof for you available as day rentals (Available within Charlottesville).

Virginia's Spectacular Scenery: A Guide to the Most Breathtaking Drives

Take a road trip and experience the natural beauty, cultural richness, and historic sites of Virginia. Its scenic byways span over 2,500 miles. Each turn presents an exquisite tapestry of landscapes to marvel at. In this guide, we are going to offer drives centered around Charlottesville and where you can find views of the best colorful foliage, mountain laurel, hiking trails, other points of interest of recreational significance.

Exploring Virginia's Lesser-Known Byways

Venturing away from Charlottesville, let’s uncover Virginia’s lesser-known byways. These secret routes hold a special journey unlike any other with magnificent landscapes and unexplored attractions – making it perfect for an exclusive road trip experience! To make it easy, we've created a guide on Google Maps to help guide you along the path you'll find in Google Maps is described below in this section. Also note, there are quite a few Virginia Wine stops along the way - please drive carefully.

Lets begin by starting at Route 53, just right off exit 121 on Interstate 64. Within the first two miles, you have two mountaintops to choose from, Carters Mountain Orchards or Thomas Jefferson's little mountain, Monticello, where you can see Jefferson's original historic structures. Just beyond Monticello, is Jefferson's vineyards, the birthplace to America's wine.

As you continue down 53, you will venture onto James Monroe Highway and see Morven Estate (owned by the late John Kluge, at one time the wealthiest American), James Monroe's Ash Lawn, Trump Vineyards (also once owned by the late John Kluge), or Blenheim Vineyards, owned by Charlottesville's own Dave Matthews. As you continue down the path you will find the Tasting Room & Taphouse at Mount Ida, the driveway alone is worth the drive, however, Mt Ida offers the first stop for a sit down lunch and beverage, along with an incredible 20 mile plus view of the valley and mountain views.

Next, we'll be traveling Virginia's original turnpike, Plank Rd, a quite crooked road. In 1850, the general assembly decided to plank the road to improve travel and benefit farms trying to get their goods to the James River. This was Virginia's original toll road, today, you will find no such tolls. However, you will have found a crafty way to arrive at two of Charlottesville's favorite offerings, Dr Ho's Humble Pie (Inventive Pizzas) and Pippin Hill Farm & Vineyards, an amazing scenic overlook from Pippin's terrace.

Jumping back in the car we will head past the historic town of Batesville, over to the Afton Mountain area. Once you cross over Virginia's scenic byway Route 151, you will begin to be within the Afton area. Here you will find Veritas Vineyards & Wineries, Afton Mountain Vineyards, or if you enjoy hiking trails, the Blue Ridge Tunnel - an engineering feat by General Claudius Crozet (opened 1858).

Once you reach end of Route 6, you will be at the intersection of Route 250, where if you head left (west), you can drive to the top of Afton Mountain and find both the access points to Skyline Drive (operated by National Parks) and Blue Ridge Parkway. However, since we are discussing the roads less travelled, we'll be heading east on 250, and believe us, 250 is well travelled so we'll move off it fast, however, as you drive, look to your right and you might notice a home you might find in downtown Washington within the nation's capital, yes, The White House. While, we are going to let the owner remain a mystery, the home itself is a true archaeological replica of the original White House.

In the little town of Greenwood, Virginia, you can find antique shops, and the beginning of Route 810, a drive that takes you along the foothills of the Blue Ridge Mountains. Shortly down 810, is another one of Charlottesville's favorite destinations, King Family Vineyards. Now, if you're on a literal Sunday drive, King Family offers free Sunday polo in season (Editor's note: get there early and check online schedule). 810 will take you straight through the town of Crozet and off to the town of White Hall we'll head, where once again, we have choices to make. In this town, we have Stinson Vineyards, White Hall Vineyards, Grace Estate Winery, and some of our favorite hiking trails and waterfalls at Sugar Hollow, within Shenandoah national park. At the end of 810, if you head left, which is very much worth heading left, you'll head to Sugar Hollow, a stunning drive no matter the season. If you head right, you'll be on Garth Rd that can take you back to Charlottesville, however, we still have fuel in the tank and we've only just barely completed the halfway mark.

Now since you have your foot to the pedal, you might want to stretch it. When you take a left on Ridge Rd, you might notice quite a few cars parked. Those cars are for the runners, which run the 4 mile stretch of road, that is the ridge between the Moormans and Mechums Rivers. This trail/road is not only popular amongst runners, the equestrian is also a normal site. (Editor's note: Drive slowly and please do not kick up dust, the runners will thank you).

Now that you're at the end of Ridge Rd, you can take left and you'll head to the town of Free Union, Virginia, if you're going left, we are going to just get some wind in the hair for a bit on another crooked road. While there quite a few spots along the way, we're getting over to Barboursville Vineyards where you find more wine and historic structures.

Now that we are heading south down Route 20 back towards Charlottesville, of course, we need throw in a twist. Left on Turkey Sag Rd will take you over to one of our favorite scenic byway. First, we need to look out for Peters Mountain Rd off of Turkey Sag. You will notice quite a few signs that say "do not enter". Remember those signs and when you are back in cell phone range, google map search where you just were - it is rumored that this is the Vice President's nuclear bunker. You'll notice on Maps that you can drive into mountain at the top.

Now we are finishing this amazing drive with some of Charlottesville's most spectacular scenery, colorful wildflowers, and largest estates known as the Keswick area. Within this area you will find Castle Hill Cidery, Keswick Vineyards, Southwest Mountain Vineyards, and Keswick Hall - a luxurious area resort with golf course and Jean-George's Marigold.

Closing this Virginia Drive

This drive is meant to be just that, a drive. While we cannot offer an approximate time, we suggest a day given to the effort if you plan on using the entire map we've suggested at the opening. While we've suggested quite a few attractions along the way, this is in no way all encompassing of all the attractions there are or even close to the number that can be found. There are quite a few national scenic favorites.

Unveiling the Blue Ridge Parkway: America's Favorite Drive

On our Virginia road trip, the highlight is an alluring voyage down Blue Ridge Parkway - a 469-mile stretch through America’s beloved Appalachian Mountain chain. Along this drive you will find breathtaking sights such as rock formations, mesmerizing waterfalls and historic constructions. There are numerous scenic overlooks to visit including Mabry Mill which offers some of the most stunning photography opportunities and Humpback Rocks Visitor Centre where you can become acquainted with early mountain settler life, from days gone by To bewitching beauty throughout the Great Smoky Mountains at Primland Resort where immersing yourself in its lifestyle only heightens your experience. All these elements blend together to make for a memorable journey along the Blue Ridge Parkway!

Journeying Through Virginia's Shenandoah National Park on Skyline Drive

The Shenandoah National Park in Virginia offers a stunning Skyline Drive, a national scenic byway, measuring 105 miles of breathtaking vistas and most spectacular scenery. It is an ideal destination for nature lovers providing wild safari experience with herds of deer, eastern black bears, as well as various types of songbirds set against the majestic backdrop of the Blue Ridge Mountains along the route. Easily accessible from four main points on Rt 66 near Front Royal or Rt 64 at Rockfish Gap makes this drive perfect for any road trip plan plus visitors can opt to stay longer by staying either at Skyland Lodge, Big Meadow or Lewis Mountain cabins available nearby. The park’s beauty changes seasons throughout spring to late summer & fall bringing out Enchantment making each visit different than before offering blooming azaleas April onwards until mid November where vibrant foliage paints landscape till then.

Coming from Charlottesville, we suggest using Interstate 64, and getting off at Exit 99. Here you can enter the national park (or the Blue Ridge Parkway) at Skyline drive's most southern entrance. Entrance fees today are $30.00 for 1 car. Driving north, the speed limit is on average around 35mph and too many scenic overlooks to mention. There are two exits from Skyline to get off of easily for Charlottesville based guests, 33 and further north is 211.

Skyline driveundefined

Our suggestion, is getting off at 211 where you can easily go east or west. If West, you can head down to the historic town of Luray and visit Luray Caverns - known for its walkable caves and antique car museum. If you head east, you head down the mountain until you reach Route 231.

At the beginning of Route 231 is the town of Sperryville, Virginia, another iconic spot for stopping looking at shops or lunch options. Continuing down 231 will take you along the base of the Blue Ridge Mountains on another crooked road drive through some of Virginia farmland. This route will take you straight to the town of Madison and past one of the most iconic Virginia hikes, Old Rag Mountain.


As we bid farewell to our tour through Virginia’s scenic drives, it is easy to be captivated by the natural grandeur of this region and its profound historical roots. From the Blue Ridge Parkway down to unknown back roads, each journey provides a unique understanding of all that makes up the Commonwealth. A vivid testament to the state’s visual splendour, these paths are like no other road trip destination.

So why not gear up your car for an incredible outing? Whether you’re into history or nature or want some cultural insight – there truly is something here for everyone! Come explore with us as we take in Virginian landscapes full of culture and beauty, let the path guide you along on your next adventure!

Click this link to see our suggested route around Charlottesville that we call 'The Road Less Traveled'

Frequently Asked Questions

What are the most scenic routes and stops in Virginia?

Planning a trip to Virginia? Look no further! The Colonial Parkway, Skyline Drive, Blue Ridge Parkway, and George Washington Memorial Parkway are all great routes with stunning views. Mount Vernon, Colonial Williamsburg, Yorktown battlefield, Monticello, Floyd country store, are all great attractions filled with history, bringing a great number of visitors to Virginia. Any local visitor center will have guides on Virginia, roads, wines, and historic sites or you can visit for information across the state.

What mountains do you drive through in Virginia?

Driving through Virginia’s Blue Ridge Mountains is an awe-inspiring adventure along the breathtaking Skyline Drive and scenic Blue Ridge Parkway. Both of these routes, touted as some of America’s finest mountain drives, offer a fantastic journey full of captivating sights to explore for all who venture out into this picturesque area. Virginia is also home to the Appalachian mountain chain, running from Georgia to Maine.

When is the best time to visit Virginia?

Spring offers the most colorful wildflowers while late September is the beginning of fall foliage. However, these are also the busiest and priciest seasons. If you want to skip the lines, save dollars on lodging, we suggest coming from late November to early Spring.

What is the famous road in Virginia along the Blue Ridge Mountains?

The Blue Ridge Parkway is renowned as a scenic drive along the mountainous region of the Blue Ridge Mountains, with its course extending from Virginia all through to North Carolina. It’s an ideal route for taking in awe-inspiring views while cruising down one of America’s best road trips!

Where can I get information more information on rental vehicles, vacation rentals, or Charlottesville?

You can call Stay Charlottesville at 434-977-0442 and generally they can help with more in-depth knowledge to questions regarding the area, vacation rentals, and activities around the area. Rental vehicles are offered by a reliable third party that we like due to the care, quality, and maintenance they take for the vehicles and of course, the fresh air and open roofs.