Freedom is the wind blasting against your body and the fresh scents of azalea, dogwood, jasmine and poor, misfortunate nocturnal creatures decomposing wafting in your helmet.
It’s a tickling stomach in a downhill run, a tingling spine when leaning into a curve and the realization that the pothole about to swallow your tire could have painful repercussions.
Freedom is taking life into your own hands and it’s the motorcyclist’s way of life.
But along the pastoral roads through pasture lands and Blue Ridge Mountain foothills in Jeffersonia, freedom is not only a way of life, it’s where that way was forged. Imbued with a collective love of freedom, these farmers, land owners and planters with much to lose, risked life, liberty and property to assure it for us, their posterity.
This is the region that gave birth to the Declaration of Independence, the Bill of Rights, and Manifest Destiny. Here Thomas Jefferson, James Monroe and James Madison, the country’s second, fourth and fifth presidents respectively, fomented rebellion and forged a new nation all within 60 miles of each of other.
These neighbors set the political and social stage for generations to come through insistence on freedom of speech and religion, due process of law and the purchase and exploration of the West while creating a new monetary system and judicial and military traditions.
Pretty important stuff.
Pretty great scenery, too.
Although the dead presidents are long gone, their legacies – and their homes and the roads they rode horseback – remain. Best of all, you can visit them via winding roads through mountain, wood and pasture where every apex is history and every crossroad a historical marker.
The bad news is that there is so much to see and do at each of the homes that you can’t do all three adequately in one day.
Let’s take the ride, first. Start on what state mapmakers call Route 53 and locals call Thomas Jefferson Parkway with easy enough access from Interstate 64; just take the Route 20 exit and head south for about a mile. Take a left on Route 53, and start uphill.
The east-west route from Charlottesville to the historic burg of Palmyra is a path back to Colonial times, providing access to Jefferson’s home at Monticello, Monroe’s estate at Ashlawn-Highland as well as bit of 1776 dining fare in the Michie Tavern.
The tavern, the first stop on Route 53 just outside of Charlottesville, is an historic anomaly. Although it provided lodging for Colonial wayfarers, its original location was in a different part of Albemarle County, the county that plays host to Monticello and Ash Lawn. It was moved to its current location to take advantage of the revolutionary atmosphere of Route 53.
Michie Tavern serves traditional Colonial-era lunches from 11 a.m. to 3:30 p.m. in “The Ordinary,” including delicious fried chicken and stewed tomatoes that even tomato haters can appreciate. More modern fare is also available for those with 21st Century taste buds, but the retro buffet served by folks in period costumes is worth the time and hunger.
Guided museum tours are entertaining and informational, but let’s save the Tavern’s filling fare for a time of true hunger, like at the end of a 90-mile ride along great roads..
Just two miles east of Michie Tavern is the driveway of Jefferson’s Monticello. Found on the back of the nickel, Monticello was a home in progress during Jefferson’s time as he continually added, changed and enlarged the building, hiring skilled craftsmen and training slaves to do everything from forging nails and making bricks to making wine.
Gardens, which once surrounded the home, still bloom with plants that grew in Jefferson’s soil 230 years ago. Research into Jefferson’s thoughts and deeds as well as the home’s history, continues by historians at the Thomas Jefferson Memorial Foundation, which owns the property.
Mr. Jefferson was a member of the Continental Congress, and chosen by peers in 1776 to write the Declaration of Independence, a most radical document at the time, proclaiming all men to be equal regardless of birth, wealth or status and making government the servant of the people.
In 1800 he was elected president, the first president of an out-of-power party to take over the White House and served two terms. He also designed the University of Virginia in Charlottesville, a sight to tour in its own right.
From Jefferson’s place, it’s 1.5 miles of tree-lined S-curves and sweepers climbing toward Route 795 and a right turn that leads directly to James Monroe’s Ashlawn-Highland home.
Monroe, a Jefferson protégé and member of Madison’s cabinet, took over the presidency after the War of 1812. He’s most famous for the Monroe Doctrine warning foreign powers to stay out of the Americas, including Central America or face conflict with the fledgling nation.
Less majestic, perhaps, than Monticello, Ash Lawn-Highland has a niche of its own as a working farm and arts center. Summer stock opera is held outdoors at Ash Lawn with national and international talent.
Livestock from chickens to cows to peacocks still roam the grounds at the Monroe estate and have been known to provide impromptu solos during the operas.
Backtracking east, Route 795 ends at Route 53 and a right turn leads to scenic back roads winding through grazing country dotted with hard-scrabble farms. Unfortunately, the most recently raised crop in the area is the suburban subdivision. Luckily, the road is lightly traveled after and before weekday rush hours and the pavement is good for less experienced riders and a pleasure for those with heavy right wrists.
A word of caution, however: Although the road is good, the road-side ditches are primitive and unforgiving should a wayward rider decide to go off road.
For those who eat to ride and ride to eat, there are few traditional grocery stores or 7-Eleven outlets in the area to get munchies or sodas for saddlebag snacks. Luckily, there are numerous country store-style establishments, many offering exotic coffee, excellent microbrewery beers and great barbecue.
Route 53 T-bones at U.S. 15. Taking a left turn to the north leads to Palmyra, a town with its own war history and heroes, both Revolutionary and Civil.
Old town Palmyra is a sleepy section of brick buildings well over 100 years old and some up to 170, such as the Old Stone Jail. The jail, now a museum with its rooms converted to show off the 200 years of Palmyra’s past, boasts three-foot thick concrete walls and even an aged metal cage for more violent offenders.
In the town square stands an obelisk and cannon honoring the town’s fallen Confederates, a reminder that there are many interpretations of freedom for which men will lay down their lives.
New town Palmyra along U.S. 15 is a cluster of gas stations and convenience stores that shows the road’s increasing importance as a transportation corridor for the area. The region is becoming more suburban and urban through residential and commercial development but has yet to lose its charm as a scenic ride.
The two-lane pavement rolls in a series of rises past old industrial properties, old farms and new developments and into the booming dot on the map dot that is Zion Crossroads.
If you’ve worked up a hunger, The Crescent Inn at the intersection of U.S. 250 and U.S. 15 provides a bit of old-time, family-owned, low-cost restaurant fare. The food is good, prepared mostly from scratch and affordable. The help is also friendly and inclined to treat customers, even newbies, as family.
Keep going north and the rolling road through the foothills becomes an undulating ribbon through pastures on into the town of Gordonsville.
Gordonsville is home to history as well. The historic Exchange Hotel, now a Civil War museum, sat on a railroad line and served as a hospital during Civil War battles at Fredericksburg and two battles in The Wilderness.
Demonstrations of Civil War medical techniques at the Hotel are both inspiring and downright scary.
Following directions around the traffic circle at U.S. 15 and U.S. 33 (turn right at the Tastee-Freeze) leads to a four-lane highway lined with oaks and maples that leads into Orange and Route 20. Going west (left) leads directly to James Madison’s Montpelier.
Once owned by the DuPont family, Montpelier was built upon and added to until it was a sprawling complex of rooms and decors. It’s slowly being deconstructed back to the president’s day, a process that will continue for years and has become part of the daily tours.
Madison, known as the Father of the Constitution, helped write the document that governs our country and drafted the Bill of Rights at Jefferson’s request. He served as Jefferson’s Secretary of State.
His wife Dolley was the Washington hostess with the most, becoming well known for hospitality and penchant for creating a stir with short-sleeved dresses.
No, she did not invent the snack cake.
Even if you don’t have time for the Montpelier tour on this ride, the gift shop is open and the house can be seen from the road to the shop. It’s a nice place to shop, see a little historical film on the home and get a micro-brewed ginger ale, rootbeer or some fancy coffee.
Come back when there’s more time. For now, ride out of Montpelier, turn left and go west along the tree-lined Route 20 through lush and productive farm land. It’s a beautiful slice of Central Virginia, this official state scenic route meandering through three counties back toward Charlottesville.
On the way back, Barboursville Vineyards at U.S. 33 provides a nice rest stop. The ruins of Gov. James Barbour’s Thomas Jefferson-designed home still stand at the winery and provide a backdrop for talented local amateur actors in summer theater. It also provides a logo for the labels of some very good wines, including a champagne-like sparkling wine.
Taste testing is available and you don’t have to swallow much or any at all to enjoy the flavors.
Drive just a few miles east on Route 33 and you can visit nearby Horton Vineyards as well. Both wineries win awards and offer exceptional products. You can also purchase their wares then and there, so leave room in the luggage.
Taking Route 20 back into Charlottesville provides some more S-curves, some decreasing radius turns, more wooded scenery and, unfortunately, increasing traffic.
The road ends up at U.S. 250 and the congested area of Charlottesville known as Pantops. Turn right and get into the left lane to turn at the next light, just over the bridge. Follow the Route 20 signs through town and it will lead you full circle to Route 53 and a well-deserved dinner at the Michie Tavern.
Go ahead, get the Colonial buffet and try the stewed tomatoes: Feel free and be brave.
You’re in the right place for it.




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