Every October, Annapolis residents fall into the same rhythm without thinking much about it. Park somewhere out of the way, walk in, meet friends at a bar that's been there longer than the boats have. That rhythm held for decades because City Dock itself didn't change much from one fall to the next.
It has changed this year. The shows are back on the same weekends residents expect, but they're setting up on a waterfront that's mid-renovation, and the construction fencing is already rewriting where the docks, the crowds, and the parking end up.
Two Weekends, Less Dock to Work With
The Annapolis Powerboat Show runs October 8 through 11, and the Annapolis Sailboat Show follows October 15 through 18, both at City Dock, according to the Annapolis Boat Shows event pages.
| Show | Dates | Location |
|---|---|---|
| Annapolis Powerboat Show | October 8-11, 2026 | City Dock |
| Annapolis Sailboat Show | October 15-18, 2026 | City Dock |
That part of the calendar hasn't moved. What has moved is the ground underneath it. In April 2026, the city announced that the Spring Sailboat Show had to shift its setup into the top of Ego Alley and portions of Randall Street, explaining that ongoing City Dock construction on lower Dock Street had eliminated the usual footprint. That closure hasn't been resolved since April. There's no reason to expect the fall shows will look any different from the spring one.
What the Construction Is Actually Doing to the Dock
The project reshaping City Dock is a flood-resiliency build, not a cosmetic upgrade. It calls for a raised park at the end of Dock Street, a new Maritime Welcome Center, and a preserved Burtis House, paired with a movable flood barrier system meant to answer flooding that has become an increasing problem for Ego Alley businesses, residents, and visitors, according to The Baltimore Banner. The full project carries an $87.8 million price tag, and as of March 2026, Mayor Jared Littmann called it fully funded after a final FEMA grant came through.
Fully funded doesn't mean finished. Reporting from Eye On Annapolis in August 2026 lays out a schedule that runs the current phase through May 2027, with a second phase continuing from May 2027 through March 2028. That later phase is expected to close upper Dock Street between Randall and Craig Streets entirely, the exact stretch where most of the surviving merchants sit. Both this October's shows and next October's will happen somewhere inside that window.
The city knows the calendar doesn't pause for construction. A recent progress update acknowledged as much directly: "The City is aware of the need to make room for the boat shows in October."
The Streets That Go Resident-Only Again
The parking restrictions that show up every boat show season haven't changed shape, even if the dock behind them has. For both the 2024 fall shows and the 2026 spring show, the city closed the same three streets to everyone except holders of a residential parking permit for that stretch of downtown:
- Prince George Street, from Craig Street to East Street
- East Street, from Prince George Street to King George Street
- Randall Street, from Prince George Street to King George Street
Everyone else gets routed to the four rotating city garages, Hillman, Knighton, Gotts Court, and Park Place, connected by the free Magenta shuttle that loops downtown all day during both shows. Rideshare pickup gets consolidated to a single designated spot at 7 St. Mary's Street rather than scattered along Dock Street.
One change worth knowing about: the rebuilt Hillman Garage, sitting about 500 feet from Market Space, added 165 parking spaces this year specifically to absorb the overflow created by construction-related closures elsewhere downtown. If Hillman used to be crowded by early afternoon on a show day, it has more room to work with now than it did last fall.
The Shops Absorbing Two Hits at Once
For the merchants who line Dock Street, this fall's shows land on top of an already difficult year, not before one.
Sveinn Storm, who owns Storm Brothers on Dock Street, told Eye On Annapolis that sales fell by roughly $98,000 during the construction project's first year, and that by mid-July 2026, the business was running another $98,000 behind that already-reduced baseline. Storm owns his building outright, which keeps him from walking away, but it doesn't cover payroll or inventory.
"I have to sell assets to keep my business going until the end of this."
He's not alone. A Dock Street gallery that opened its doors in 1978 has told a Baltimore television station it plans to close its storefront by the end of 2026, citing a sales decline of more than 70 percent tied to lost parking, construction fencing, and reduced foot traffic. A business that survived nearly five decades of Annapolis weather didn't survive this particular stretch of construction.
That's the part of this fall's boat shows a resident is better positioned to understand than a visitor flying in for the weekend. The two-week crush that used to be a predictable annoyance is now landing on merchants who are already down two consecutive years of revenue before the first boat ever gets craned into Ego Alley.
The Workarounds That Still Work
The informal playbook residents have used for years still mostly applies, with one caveat: the entry points and sightlines have shifted along with the construction.
Parking at the Eastport Elementary lot and walking over the Spa Creek bridge remains one of the more reliable options for anyone driving in, since it sits on the opposite side of the harbor from the construction zone entirely. Drivers who do park in a downtown garage often find less backup entering from Duke of Gloucester Street than from the Dock Street side, since that's not where the crowds funnel toward the fencing.
The Annapolis Water Taxi keeps running through both shows, reachable at 410-263-0033 or VHF channel 68, and it sidesteps the parking question altogether for anyone coming from Eastport or a mooring on Spa Creek.
As for where to actually eat once you're downtown, the spots that have outlasted a dozen boat show seasons are still the ones locals mention first: McGarvey's Saloon, Middleton Tavern, and Boatyard Bar & Grill over in Eastport all keep serving through the crush without turning into tourist traps, according to longtime residents who've lived through the shows for decades.
What This Actually Means for the Next Ten Weeks
The old advice for boat show season was simple: don't fight it, plan around it. That's still true. What's different this year is what "showing up" actually accomplishes.
Eating on Dock Street during show week, or walking past the fencing to a shop that's stayed open through two years of construction dust, carries more weight this October than it did five years ago. The merchants absorbing both a construction slowdown and a compressed show footprint are counting on the same foot traffic that used to be automatic. Choosing to walk that stretch on purpose, rather than routing around it entirely, is a small thing that means more this year than it used to.
Annapolis residents already know how to get through boat show season. What's worth updating is the assumption that the dock underneath it hasn't changed. It has, and it will keep changing through at least next spring.
If you're weighing a move within Annapolis, or wondering what a waterfront-adjacent property looks like once City Dock's construction wraps, the team at Paul Wesley Real Estate knows this stretch of Anne Arundel County well beyond the two weeks in October when everyone else is paying attention. Contact us when you're ready to talk about what's next.
