Touring the Byway
60 miles | 4 Days / 3 Nights | Gateway City: Charlottesville, Virginia

We recommend starting your journey in the very delightful town of Charlottesville, where you can explore some of Virginia’s most important history. Thomas Jefferson lived here, as did President James Monroe. President James Madison was just up the road. The three, who together governed America for 25 years, were friends, often seen together talking on a street corner in Charlottesville. You can spend the day exploring Jefferson’s Monticello, Monroe’s Highland, and the original campus of the University of Virginia, with a period lunch at Michie Tavern. You can also stroll Charlottesville’s very unique downtown mall, an eight block bricked area in the center of town, lined with historic buildings filled with shops, boutiques, and restaurants.

After a good night’s sleep at the South Street Inn, located right off the Downtown Mall, the most efficient way to get to your next destination would appear to be to jump on Interstate 64 to cruise down to Lexington. Yet, if you’re not in a hurry, you don’t have to do that. There are absolutely beautiful country roads to take cross country to avoid the interstate all together. On the other hand, stretches of Interstate 64 that you’ll be on, travel through some really lovely Virginia countryside.

View the Detailed Itinerary below to see the full route, which is complete with dining, shopping, and lodging recommendations!

Highlighted Attractions


You’ll never forget your first glimpse of Jefferson’s beloved home Monticello, (“little mountain”), a white domed, red brick jewel surrounded by elegant landscaping.  The house, listed on the National Register of Historic Places, is also a National Historic Landmark and earned a place on the World Heritage Treasures list of the United Nations. The house itself contains 43 rooms on a plantation originally encompassing 5000 acres. Begin your visit with a guided walk through the house that includes the cellar, gardens and vineyard.  About 60 percent of the furnishings are items original to Jefferson.  The plantings in the vineyard are descended from the original vines Jefferson brought back from France. Little did he know that he was starting a whole new enormous industry in the United States with these fragile plants.  The rest of Monticello is dotted with interpretation revealing as much as possible about Jefferson’s strong legacy and contributions to the United States. Spend plenty of time exploring the whole property, there’s a lot to the story. 

The Homestead

Experience the elegant charm that has made The Homestead a destination for 23 U.S. presidents over more than 250 years. Encompassing more than 2,000 acres of scenic landscape, the resort delivers timeless comforts and plenty of activities, no matter the season. The property dates from 1766, when a lodge was built on the site. Later, Dr. Thomas Goode expanded it with a European style spa and hydrotherapy. The current resort dates from 1888-1892 when J. P. Morgan bought the property and started rebuilding from the ground up, completing the main building in 1902.  Be sure to take a tour of the property to learn the whole history and important events that have taken place here. 

Jefferson Pools

Legend has it that the springs at Warm Springs were discovered by a Native American brave, enroute to a tribal council in the 1600s came upon these warm pools, soaked his weary body and left refreshed, quickly telling others. The trek to Warm Springs to “take the waters” was born. Soon it became the custom for European style “spa houses” to be built over warm springs all over the country. The pools here were constructed in 1761 in an octagonal-shaped house with a large hole in the roof to let out steam from the 98-degree springs. The original gentlemen’s bathhouse is referred to as the Jefferson Pools because Thomas Jefferson soaked daily for three weeks to help his rheumatism. A similar women’s bathhouse was added several decades later.  

Downtown Charlottesville

Main Street hosts a vibrant collection of more than 120 shops and 30 restaurants (many with outdoor cafes) housed in a wonderful mix of restored and renovated historic buildings. Dine, shop, see a movie or a play, or just stroll the brick-paved area.  Even in the fine restaurants, no need to worry about a tie, just dress neatly and you’ll be fine.

Lexington Carriage Ride

Discover Lexington to the relaxing rhythm of clopping hooves on a 45-minute narrated carriage tour through downtown, residential areas, and the Stonewall Jackson Memorial Cemetery.

To experience all that Cascading Waters, Mountain Drives has to offer, download the complete itinerary! 

The detailed itinerary includes: