10/28/2026
Eastport Declared War on Annapolis. The Best Part Had Nothing to Do With Winning. 🏴☠️
For a few minutes Monday evening, Eastport's invading army couldn't even get through the doors of Annapolis City Hall.
They had the flags. They had the chants. They had a declaration of war to deliver.
Apparently, conquering Annapolis requires a little patience.
When the doors finally opened, the Maritime Republic of Eastport marched into the City Council chambers in a wave of yellow flags, pirate hats, and what I can only describe as controlled chaos.
I was there to photograph it. But what stayed with me wasn't the invasion. It was the people.
In a city as rooted in history and tradition as Annapolis, I think that's a story worth telling.
Earlier that evening, I'd found a seat near the end of the bar at Federal House, watching Eastport residents and supporters gather for their annual declaration of war. There were songs, chants, laughter, and plenty of friendly insults aimed at the other side of Spa Creek.
It was loud, a little ridiculous, and unmistakably Eastport.
Raoul Graves had invited me to document the evening from Eastport's point of view. At first, the assignment seemed simple enough: capture a community having some fun at its neighbors' expense.
But there's a reason this tradition has survived for nearly three decades, and it goes deeper than pirate hats and bragging rights.
⚓ A LITTLE HISTORY BEHIND THE REBELLION
Annapolis knows its history. It's written into our streets, preserved in our buildings, and woven into traditions that reach back to the earliest days of the country.
But not every tradition worth keeping began centuries ago. Some started with a closed bridge, a frustrated neighborhood, and a few drinks.
In 1998, plans to close the Spa Creek Bridge for repairs threatened to cut Eastport businesses off from the rest of Annapolis. Rather than accept their fate, Eastport residents answered with creativity and a considerable sense of humor.
They declared independence.
The Maritime Republic of Eastport was born.
Eventually, the bridge controversy faded and life returned to normal. But something had changed. A neighborhood had found a new way to celebrate who it was, and the people who lived there had no interest in letting it go.
Nearly thirty years later, that spirit is still alive.
🏛️ WHEN CITY HALL JOINED THE FUN
On Monday evening, that spirit marched straight into the Annapolis City Council chambers.
Eastport's representatives proudly presented their declaration of war, making their case for the superiority of their beloved neighborhood. Mayor Jared Littmann and members of the City Council answered with good-natured humor of their own.
Parking, naturally, became a punchline. So did the ongoing City Dock reconstruction, which has once again pushed this year's Tug of War entirely onto Eastport's side of Spa Creek.
These weren't generic jokes. They were the kind that only land when you've spent enough time in Annapolis to know exactly what everyone is laughing about.
The room loved them.
Throughout the ceremony, I moved around the chambers, front to back and side to side, and kept noticing the same thing.
People were smiling.
Not just the Eastport crowd. City employees, officers, elected officials, and residents who had come for regular council business were all laughing together.
For a little while, the usual business of City Hall gave way to something different: the people who govern our city and the people who call it home sharing a moment that belonged to all of them.
There was something genuinely refreshing about that.
❤️ BEHIND THE LAUGHTER, SOMETHING MUCH BIGGER
At one point, an Eastport representative spoke about the money the Maritime Republic has raised for charitable causes over the years.
The room erupted in cheers.
That's where the real significance of this tradition becomes impossible to ignore. Through its events, the Maritime Republic of Eastport has raised hundreds of thousands of dollars for local charities.
Think about the irony. An organization built on the idea of separating from Annapolis has spent nearly three decades bringing its community closer together.
The rivalry is pretend.
The generosity isn't.
The people who make that possible deserve some recognition, and Raoul Graves is one of them. In 2025, the Community Foundation of Anne Arundel County named Raoul its Volunteer of the Year, honoring thousands of hours of service to local organizations, children, and families.
But Raoul is hardly alone. Behind traditions like the Tug of War are countless volunteers, organizers, local businesses, and residents who give their time to make it happen. They aren't looking for recognition. They simply care about where they live.
Maybe that's the part of the story that deserves more attention.
🪢 THE TRADITIONS WE'RE STILL CREATING
By the time Eastport's forces marched triumphantly out of City Hall, the declaration had been delivered, the jokes had landed, and the latest chapter of this unusual rivalry had been written.
Then the conversation turned to more pressing matters, like where everyone was going for their next drink.
On Saturday, November 7, Eastport and Annapolis meet again for the annual Tug of War, starting at noon on Second Street in Eastport. Expect cheering, competition, neighborhood pride, and a healthy amount of trash talk, all for a good cause.
But after Monday night, I see the event a little differently.
We live surrounded by reminders of the people who came before us. From the State House to the Naval Academy, Annapolis has spent centuries preserving its history and honoring its traditions, and rightly so.
But history isn't only something that happened here hundreds of years ago. It's happening around us: in our neighborhoods, inside our local businesses, at community gatherings.
And sometimes inside City Hall, where a group of people in pirate hats can declare war on their neighbors and somehow leave everyone feeling a little more connected.
Traditions don't survive because they're old. They survive because people care enough to keep them alive.
That's what I saw Monday night. Not just a neighborhood celebrating its independence, but a community building an identity that future Annapolitans may look back on with the same affection we feel for the traditions we inherited.
For all the talk of Eastport declaring war on Annapolis, I walked away thinking about how much these neighbors are willing to do for one another.
Annapolis has spent centuries making history. What I saw Monday night was a community making sure its traditions have a future.
That might be the greatest victory of all.
📍 Tug of War: Saturday, November 7 | Noon | Second Street, Eastport
Come out, pick a side, and support a great cause.
📸 Photos: Mike Triolo | Treeolowphoto
