Five Streets for a Stroll Through Time

There's just something about original roadways that tugs at my heartstrings. Seeing historic sites on their own is great, but walking on 200-year-old cobblestone paths to reach them is, for me, the pinnacle. It humanizes the past in a weird way, in a way that perfectly paved concrete never can. Bonus points if the cobblestone is worn down in certain spots, a path within a path carved by centuries of hastily pressed footprints landing within each other, creating a roadmap of where our ancestors stood. It brings a literal meaning to following in their footsteps.

Although not all the streets listed below retained their cobblestones, each recognizes its historic lineage in its own way. Some have embraced the commercial while others are purely residential, but they all have the unique quality that makes the distance of time seem just a little shorter, where you can just as easily be in the 18th or 19th century as you are in the 21st.

Ferdinand Street: St. Francisville, LA

The entirety of downtown St. Francisville is on the National Register of Historic Places. It's a quaint place, almost unbelievably so, where children ride their bikes in the street and everyone knows everybody. From being the largest port on the lower Mississippi River to the capital of the Republic of West Florida to the place where the Civil War stopped for a day, there's a lot of history packed into this strip of land known for being "two miles long and two yards wide."

Stretching up from the river and through the shopping district, Ferdinand Street is the main thoroughfare. Buildings here date back to the early 1800s and are in the Spanish Colonial and Neo-Classic styles, almost all identified by markers with their names and construction dates. Wide sidewalks and overflowing shade trees make this an easily walkable town, and the West Feliciana Historical Society offers maps and recommendations for your self-guided tour. Along the way, keep an eye out for the cedar oak, two trees in one!

Old Main Street: Maysville, KY

One of the first American settlements west of the Appalachian Mountains, Washington was founded in 1786, experienced rapid growth through the 1840s, and has changed little since then. Annexed by nearby Maysville in the 1990s, today Washington is known for its log cabins, brick manors, and multitude of museums. Like St. Francisville, Washington packs a lot of history into a little space: Within a few blocks, you can see the last-known 18th-century flatboat house, the courthouse lawn where Harriet Beecher Stowe was inspired to write "Uncle Tom's Cabin," and the childhood home that housed not one but two Civil War generals — one Union, one Confederate.

Old Main Street runs alongside a section of original cobblestone road and is the primary gateway to Washington. Although most of the structures have exterior interpretive signage, I recommend booking a guided tour through the visitor's center for full access to the buildings and a behind-the-scenes look at the region's colorful history. The tourist season runs from March to December.

Original cobblestone streets of Old Washington

Lauderdale Street: Mooresville, AL

Mooresville, "Alabama's Williamsburg," is one of the oldest towns in the state and home to one of the oldest post offices in the country. Today, Mooresville is primarily residential but does open its historic structures for special events and guided tours. With a population of right around 47, everyone truly does know everyone else, and they're always proud to welcome visitors.

Two of the four most historic structures sit side-by-side on Lauderdale Street: the old brick church, unique for its hand-shaped steeple, and the aforementioned post office, where some box numbers have been in the same family for generations. If you're going the self-guided route, stop by Dogwood and Magnolia Bakery first to pick up a walking tour map. While you're there, make sure to visit the antiques room in the back, where you'll find a surprisingly extensive array of artwork and bric-a-brac.

Mooresville Brick Church (note the hand-shaped steeple)

Bluff Street: Dubuque, IA

Iowa's oldest city, Dubuque, is known for its history, having several structures on the National Register of Historic Places, but nowhere does that history feel closer than on Bluff Street. Lined with perfectly preserved Victorian buildings nestled at the foot of a tree-clad bluff, it is easy to feel lost in time here, where residential buildings mingle with specialty shops. In a way, it feels insulated, like a 19th-century village within a 21st-century town. Historic and eclectic, over the span of a couple blocks, you'll find a store specializing in Irish products, a mom-and-pop confectionary, and a fair trade gift shop.

Just off Bluff Street is the Fenelon Place Elevator, also known as the world's shortest and steepest railway. Originally built in the 1880s to ease the commute from the neighborhood on top of the bluff to the businesses at its foot, the funicular provides views of downtown Dubuque and the Mississippi River, plus parts of Illinois and Wisconsin.

Bluff Street

Potkopinu Trail: Fayette, MS

The oldest road of all is a piece of the puzzle of the Natchez Trace, a 10,000-year-old forest footpath stretching roughly from Natchez, Mississippi, to Nashville, Tennessee. Over the course of its history, it has been traversed by prehistoric animals, Native Americans, pirates, immigrants, and presidents. In some areas, all that foot and wagon traffic literally wore the path down, creating sunken roads.

Although much of the "Old Trace" has vanished into history, these sunken roads remain, and you'll find the longest section just outside of Fayette, Mississippi. Stretching about three miles long and — in some places — over 20 feet deep, the Potkopinu Trail is the most dramatic of the sunken roads, the closest you can get to time travel.