Walk down Dock Street this week and you will hit chain-link before you hit water. That is not new. What is new is a piece of paper sitting on the city's Special Events page that quietly changes the terms of the conversation: Annapolis has now made its construction-era event routing official policy through 2028, not just for this fall, but for the fall after that, and the one after that.
If you have lived here through even one boat show season since the City Dock Resiliency Project broke ground, you already know the drill. Tents move. Streets close in different places than they used to. The Maritime Republic of Eastport marches somewhere new. What you may not know is that the city has stopped treating these as one-off inconveniences to be undone as soon as possible. The routing changes are now the plan, not a placeholder for the plan, and that distinction matters for how you spend your October and November.
The fence isn't a countdown clock anymore
Since the project broke ground last November, most of downtown treated the disruption like weather: annoying, temporary, something to wait out until the ribbon cutting. The city's own Special Events office has now said otherwise in writing. Its notice covering 2026 through 2028 states plainly that the modifications to parade and event routes are required because of "active construction at City Dock" and that they apply to every major event downtown, the St. Patrick's Day Parade and the Annapolis Boat Shows included. The notice goes further than most residents realize: a proposed route running events through Randall Street to Prince George Street was reviewed and rejected outright, because it would compress residential parking and slow emergency access in a neighborhood that is already absorbing construction detours.
That single rejected route tells you something the flood-barrier renderings do not. The city isn't improvising block by block anymore. It is running actual traffic and safety analysis on how a full calendar of signature events fits around a job site that is targeting completion around March 2028, meaning roughly a year and a half of construction still ahead if the timeline holds. Businesses along lower Dock Street, including the Annapolis Marine Art Gallery, which has operated from the same storefront since 1978, have spent nine months of this construction phase behind fencing with reduced parking out front. The gallery's owners, Kate and Samantha Wilkerson, have been candid about the toll that takes on foot traffic. Their frustration is fair. It is also exactly the kind of friction the new routing policy is trying to manage on a multi-year basis instead of re-litigating every season.
What the boat shows look like without their usual tents
The clearest evidence of that shift is sitting in the calendar right now. The Annapolis Powerboat Show runs October 8 through 11, and the Annapolis Sailboat Show follows October 15 through 18, both still anchored at City Dock. But the traditional A and B exhibit tents that have framed the shows for years will not be part of this year's layout, because the ground they normally occupy is inside the active construction footprint. Annapolis Boat Shows worked with the city on a redesigned footprint to accommodate the loss, and that redesign builds on a dry run the organization already completed this spring.
The April 24 through 26 Spring Sailboat Show tested the adjusted geometry first, shifting setup to the top of Ego Alley and portions of Randall Street rather than the usual lower Dock Street staging area. It was not a small ask. That show brought in 37 sailboats and roughly 103 participating businesses, and organizers leaned hard on downtown merchants to make the reshuffled footprint worth the trouble, running a March campaign that let shoppers at eleven Dock Street businesses scan a QR code for free show tickets. Boat Shows communications coordinator Ryan Gullang described the goal plainly: bring in as many businesses as possible to actually present at the show, rather than let the construction fencing cut them out of an event that has historically been one of downtown's biggest annual revenue days.
The city helped from its end too, extending the Magenta Shuttle route to improve access to Dock Street and adding signage to make clear which storefronts behind the fencing are open. Merchants like Randi Sadlik, who owns The Big Cheese and Sammy's Deli, are counting on the fall shows to do for them what the spring show was supposed to do: turn foot traffic into actual sales instead of window shopping past a construction wall. Annapolis Boat Shows president Mary Ewenson put the tradeoff in perspective when construction first began, comparing the inconvenience of building around a job site to the alternative of running the shows through recurring flood damage. Her comment stuck with the local coverage of the groundbreaking, and it's aged well: working around a fence is still better than wading through the show in rubber boots.
The Tug of War already found its new home, and it isn't going back
If you want proof that the city's multi-year routing policy is more than a bureaucratic notice, look across Spa Creek to Eastport. For decades, the Maritime Republic of Eastport's annual Tug of War, known locally as the Slaughter Across the Water, stretched a rope more than 1,600 feet across the creek, with tuggers lined up at Susan Campbell Park on the Annapolis side and at the end of Second Street on the Eastport side. It is one of the odder and more beloved fixtures of the fall calendar, born in 1998 when Eastport residents jokingly seceded from Annapolis after a bridge closure cut them off from downtown.
In 2025, the event moved entirely onto land. Because the construction footprint made the traditional cross-creek setup unworkable, the whole competition shifted to Second Street in Eastport, tugging teams and all, with the festival atmosphere, food vendors, and live music packed into that one corridor instead of spread across both sides of the water. Organizers didn't treat it as a downgrade. They leaned into it, turning Second Street into the entire event footprint and telling attendees plainly that parking would be tight and that arriving on foot, by bike, scooter, water taxi, or rideshare was the better call. Given that the city's own routing policy now runs through 2028 and treats City Dock's construction footprint as a fixed constraint rather than a temporary one, there's no indication the Tug will move back to the water anytime soon. The smarter assumption for anyone planning around it this November is that Second Street is not a detour. It's the venue now.
How to actually plan around it this fall
None of this means the season is diminished. It means the logistics reward a little more attention than they used to.
- For the Powerboat Show (October 8-11) and Sailboat Show (October 15-18), expect the show footprint to route around the missing A and B tents. Check the Annapolis Boat Shows site closer to each date for the finalized map, since the layout is still being finalized in coordination with the city.
- Park at the Hillman Garage rather than hunting for curbside Dock Street parking that no longer exists in the construction zone, and use the extended Magenta Shuttle to close the last stretch on foot.
- If a Dock Street shop looks closed behind the fencing, it probably isn't. The city has added signage specifically because merchants report visitors assuming storefronts are shuttered when they're simply harder to see from the street.
- For the Tug of War in early November, plan to walk, bike, or take a water taxi into Eastport rather than drive. Second Street fills fast, and last year organizers were explicit that cars were the wrong call.
The season is still here, it just moved
The instinct after a year of fencing and rerouted tents is to wait for the ribbon cutting before fully re-engaging with downtown's fall calendar. That instinct is understandable and also a little out of date. The city has now formalized its approach to running major events through 2028, which is a tacit admission that "normal" is further out than most residents assumed, and that the workarounds worked out over the past year aren't stopgaps anymore. They're the operating plan.
That's actually good news for anyone who lives here. It means the uncertainty that made this spring's boat show or last fall's Tug feel improvised has mostly been engineered out. The routes are known. The parking guidance is known. The businesses that need foot traffic have been identified and are being actively steered customers by the city itself. Annapolis in October and November still delivers what it always has, sailboats stacked against a fall sky, a rope stretched taut somewhere in Eastport, and a downtown that knows how to throw a season even with a fence running through the middle of it. You just need to know where to park.
If you're weighing a move to Annapolis or thinking about what your own property looks like from a buyer's perspective this fall, Jeannine Wayson has spent more than two decades reading this market street by street. Let's connect and schedule a free consultation.
