January 1, 1776. British naval forces under Lord Dunmore opened fire on Norfolk from the harbor — then Loyalist and Patriot forces burned what remained. One of the largest cities in colonial America was reduced to rubble in a single day.
Most people who live here have no idea that happened. And that's exactly why I wrote this.
I've been a real estate agent in Norfolk and the surrounding Hampton Roads area for over 20 years. My family lives here. I've driven these streets thousands of times. But the more I've dug into the history of this region, the more I've come to believe that Norfolk is one of the most historically significant — and most underappreciated — cities on the entire East Coast.
With VA250 celebrations underway across the Commonwealth, there has never been a better moment to actually stop the car, get out, and explore. This is my history lover's guide to Norfolk: the must-visit sites every local should see at least once.
Start Here: The Cannonball Trail
If you want one single thing that ties all of Norfolk's history together, start with the Cannonball Trail. It's a self-guided walking tour that winds through 400 years of Norfolk and American history — from colonial foundations to the Civil War to the rise of the world's largest naval base.
The trail is free, it's walkable, and it will completely change how you see downtown Norfolk.
One of the first stops most people make is St. Paul's Episcopal Church, which dates to 1739. It is the oldest surviving building in Norfolk — the only structure that made it through the burning of 1776 and every conflict since. And embedded in the exterior wall, still visible today, is a cannonball from Lord Dunmore's bombardment. It has been there for nearly 250 years.
Think about that the next time you're stuck in traffic on Granby Street.
The Naval History You Can't Miss
Norfolk has been a naval city almost from the beginning, and nowhere does that history come alive more vividly than at Naval Station Norfolk — the largest naval station in the world. While access to the base itself is restricted, the Hampton Roads Naval Museum inside Nauticus downtown is fully open to the public and is genuinely one of the best military history museums in the country.
You can walk the decks of the USS Wisconsin, a retired Iowa-class battleship that served in World War II, Korea, and the Gulf War. It is docked right there on the waterfront. The ship is 887 feet long and her 16-inch guns could hurl a projectile the weight of a Volkswagen Beetle more than 20 miles.
For anyone who has grown up here with the Navy as background noise — jets overhead, sailors downtown, ships on the horizon — standing on that deck puts the whole thing into perspective.
Freemason Abbey and the Streets That Survived
The Freemason District is Norfolk's oldest residential neighborhood, and walking those brick streets is the closest thing to time travel this city offers. The building that houses Freemason Abbey Restaurant dates to 1873, originally built as a church, making it one of the oldest standing structures in the city.
The neighborhood itself survived much of what Norfolk threw at it — yellow fever epidemics, the Civil War occupation, urban renewal campaigns of the 20th century that demolished large sections of what could have been a remarkable historic district. What's left is worth protecting and worth visiting.
When I show buyers properties in Norfolk's historic core, I always encourage them to spend an afternoon walking Freemason before they decide anything. The neighborhood tells you something about the city's character that no listing sheet ever could.
Why Norfolk's History Matters to Anyone Living Here Today
Here's the thing I've come to believe after two decades working in this market: the history of a place is baked into the land values, the neighborhood patterns, the flood maps, the street grids. Norfolk was built, burned, rebuilt, occupied, and rebuilt again. That's not just a trivia fact — it explains why certain parts of the city look the way they do, why some blocks feel rooted and others feel transient.
Virginia Beach, Chesapeake, Suffolk, Hampton — every city in this region has its own history threading through it. But Norfolk is where so much of it started. Founded in 1682, it was the commercial and political center of coastal Virginia for generations before the Revolution scrambled everything.
The VA250 commemoration is a rare opportunity to reconnect with that story. The sites are here. The trails are marked. Most of them are free. There is no good reason for any Hampton Roads local to have driven past the cannonball in St. Paul's wall a hundred times without stopping to look at it.
Go look at it.
Frequently Asked Questions
What is the Cannonball Trail in Norfolk and how do I do it?
The Cannonball Trail is a free, self-guided walking tour through downtown Norfolk that covers more than 400 years of local and American history. You can pick up a map at Nauticus or download a route from the Visit Norfolk website — most people complete the core loop in two to three hours depending on how long they linger at each stop.
Is the USS Wisconsin in Norfolk free to visit?
The USS Wisconsin is docked at Nauticus on the downtown Norfolk waterfront and is included with general Nauticus admission. The Hampton Roads Naval Museum, located inside the same building, is free and operated by the U.S. Navy — it is one of the most undervisited museums in the entire region.
What is the oldest building still standing in Norfolk, Virginia?
St. Paul's Episcopal Church, built in 1739, is widely recognized as the oldest surviving building in Norfolk. It withstood the British bombardment and burning of Norfolk on January 1, 1776, and still has a cannonball from that attack lodged in its exterior wall — visible to anyone who walks past today.