You’ve probably seen the photos. If you’ve ever scrolled through a travel influencer’s feed or looked at a postcard of Northern Virginia, you’ve seen those lumpy, uneven stones and the rows of Federal-style houses. We are talking about the 100 block of Prince Street. Most people just call it Captain's Row Old Town Alexandria. It is, without a question, the most photographed stretch of road in the entire D.C. metro area.
But here is the thing.
Most people walk across those stones, take a selfie, and leave without actually realizing what they are standing on. It’s not just "old." It’s a specific kind of survival. While the rest of Alexandria modernized, paved over its past, and built massive waterfront condos, this single block stayed stubborn. It’s narrow. It’s notoriously difficult to walk on in heels. It’s also the soul of the city.
Honestly, if you want to understand why people pay millions of dollars to live in drafty houses built in the 1700s, you have to start here.
The Cobblestone Myth vs. Reality
Let's clear something up right away. People call these cobblestones. They aren't. Technically, they are Belgian blocks or, more accurately in this specific case, river stones.
Legend says Hessian prisoners of war laid these stones during the Revolutionary War. While that makes for a great ghost tour story, historians like those at the Office of Historic Alexandria will tell you the timeline is a bit murkier. What we do know is that these stones were used as ballast in ships. Think about that for a second. Ships would travel from Europe across the Atlantic, carrying heavy stones in their hulls to keep them stable in the rough water. Once they reached the port of Alexandria—which was one of the busiest ports in the young United States—they’d dump the stones to make room for tobacco, wheat, and flour.
The city, being practical and tired of the mud, used those discarded stones to pave the streets.
Walking on Captain's Row Old Town Alexandria today is a literal workout for your ankles. It’s bumpy. It’s irregular. It’s loud when a car (rarely) drives over it. But that’s the point. It’s one of the few places where the 18th century hasn't been smoothed over by asphalt.
Who Were the Captains?
The name isn't just a marketing gimmick. In the late 1700s and early 1800s, this block was the "it" spot for sea captains and wealthy merchants. They wanted to be close to the water. At the time, the Potomac River came up much further than it does now. From their front windows, these captains could literally watch their wealth sail into the harbor.
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Take Captain John Harper. He’s the guy most often associated with this block. He was a sea captain and a builder who saw the potential in this sloping street leading down to the wharf. He built many of the houses on the north side of the street in the late 1700s. These weren't just homes; they were statements.
Look at the architecture as you walk down. You’ll notice:
- Varying rooflines (because they were built at different times).
- Deep red brickwork, often in a Flemish bond pattern.
- Boot scrapers near the front doors (essential for 18th-century mud).
- Massive, heavy wooden doors with brass knockers.
It wasn't always glamorous, though. By the mid-20th century, Old Town wasn't the high-end destination it is now. It was gritty. It was a working-class port town. The fact that Captain's Row survived the "urban renewal" phases of the 1960s, which demolished hundreds of historic buildings nearby, is a minor miracle. The residents fought for it. They knew that once you pave over those stones, you can’t really get the feeling back.
Living on the Row: It’s Not All Romance
You might think living on Captain's Row Old Town Alexandria is a dream. In many ways, it is. You have a Prince Street address. You have history.
But talk to anyone who lives in a historic landmark, and they'll tell you about the "historic district" tax. You can’t just go to Home Depot and buy a new front door. If your window rot needs fixing, you’re dealing with the Board of Architectural Review (BAR). Everything has to be historically accurate, down to the paint color and the type of wood used.
Then there are the tourists.
If you live on the 100 block of Prince Street, your front steps are a public stage. You will wake up to wedding photographers, graduation shoots, and thousands of tourists peeking into your windows. It’s the price of beauty. The interiors of these homes are surprisingly narrow—many are "townhouses" in the truest sense, stretching deep back into the lot rather than wide. They have original pine floors that creak with every step and fireplaces that were once the only source of heat.
The Best Way to Experience Captain's Row
If you're planning to visit, don't just rush through. There is a rhythm to this street.
Early morning is best. Around 7:00 AM, the light hits the brick houses from the east, coming off the Potomac. The shadows of the trees stretch across the river stones. It’s quiet. You can actually hear your own footsteps, which sounds exactly like it would have 200 years ago.
- Start at the Top: Begin at the intersection of Lee and Prince Streets. This gives you the iconic downhill view toward the water.
- Look for the Plaques: Many houses have silver or bronze plaques. Some are from the Historic Alexandria Foundation, signifying the building is at least 100 years old and has maintained its integrity.
- Check the Alleys: Old Town is famous for its "spite alleys" and narrow passageways. Don't be afraid to peek (respectfully) into the gaps between the homes.
- End at the Waterfront: Once you finish the block, you're at the foot of the Potomac. Turn right to see the Old Dominion Boat Club or left to head toward the Torpedo Factory Art Center.
A Note on Footwear
This is a serious tip. Do not wear stilettos. Do not wear slick-bottomed dress shoes. The stones on Captain's Row Old Town Alexandria are polished by centuries of tires and feet. They are slippery when dry and like an ice rink when wet. Every year, at least a dozen people twist an ankle trying to look fashionable for a photo. Wear boots or sneakers. You can change into your fancy shoes once you get to the restaurant on the waterfront.
Why It Still Matters in 2026
We live in a world that feels increasingly temporary. Everything is glass, steel, and "fast-casual." Captain's Row is the opposite. It’s heavy. It’s permanent.
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It reminds us that Alexandria was once the frontier. It was a place where George Washington came to dance at Gadsby’s Tavern and where the foundations of a new country were being debated in real-time. When you stand on Prince Street, you aren't just looking at expensive real estate. You’re looking at the physical evidence of the maritime ambition that built the United States.
The stones are uneven because the world back then was uneven. The houses are close together because space near the water was the most valuable thing an entrepreneur could own.
How to Get There and Where to Go Next
Getting to Captain's Row is easy, but parking isn't. If you’re driving, try the parking garage on Union Street or the one under Market Square. Better yet, take the King Street Trolley (it’s free!) down to the water and walk the two blocks over to Prince Street.
Once you’ve done the Row, don't stop there.
- The Athenaeum: Just a block away, this bright pink Greek Revival building is a gallery and a piece of history itself.
- Gentry Row: This is the 200 block of Prince Street. It’s paved, but the houses are arguably even more grand than those on Captain's Row.
- The Wilkes Street Tunnel: If you like the vibe of Captain's Row, walk south to the old railway tunnel. It’s another atmospheric spot that feels frozen in time.
Actionable Steps for Your Visit:
- Check the Weather: If it’s raining, the stones are beautiful but dangerous. Plan accordingly.
- Photography Etiquette: Remember these are private residences. Stay off the porches and be mindful of residents trying to get their cars out of their tiny garages.
- Local Context: Visit the Alexandria History Museum at The Lyceum first to get the backstory of the merchant class before you walk the street. It makes the architecture much more meaningful when you know the names of the people who commissioned the buildings.
Captain's Row isn't just a street; it’s a survivor. In a city that is constantly changing, those lumpy river stones keep us grounded in what Alexandria actually is—a port town that never forgot where it came from.