If you live within walking distance of City Dock, your instinct every October is the same: block off the calendar, avoid Compromise Street, let the sailors have it. This year, that instinct is wrong for anyone who wants to see certain Dock Street businesses still standing next spring.
The Annapolis Powerboat Show runs October 8 through 11, and the Annapolis Sailboat Show follows October 15 through 18, with only three weekdays separating them. That's eleven days, in effect, when the harbor becomes the busiest stretch of ground in Anne Arundel County. It's also the best two weekends of the year for merchants who have spent 2026 working behind orange fencing, and this fall it matters more than usual whether their neighbors show up or stay away.
What's Actually Happening Downtown This Fall
The shows themselves aren't new. Annapolis Boat Shows has run in-water events at City Dock since 1970, and the organization notes it has connected boaters to the Chesapeake for more than 50 years. What's new is the ground they're happening on. The City Dock Resiliency and Revitalization Project broke ground in November 2025, and as of this summer the current construction phase is expected to run through May 2027, with a second phase carrying the project to a targeted completion of March 2028. Lower Dock Street has been closed for the work since the project began, according to reporting from The Baltimore Banner, and the same Eye On Annapolis reporting notes the next phase is expected to fully close upper Dock Street between Randall and Craig streets, where Storm Brothers and most of the remaining storefronts sit.
So the boat shows aren't landing on a normal downtown this year. They're landing on a construction site that has already reshaped how people get to Dock Street, and for the businesses caught inside the fence line, the two show weekends are less a nuisance to route around than a lifeline to plan for.
The Practical Stuff: Parking, the Dinghy Dock, and a Free Shuttle
If you're driving in, skip the hunt for a Dock Street spot. The city added more than 165 spaces to the rebuilt Hillman Garage, about 500 feet from Market Space, and in March 2026 extended its free Magenta Shuttle route to reach Dock Street directly, a response to the parking lost to construction, per Banner reporting. For the shows themselves, the organizers direct visitors to Navy-Marine Corps Memorial Stadium, with pre-sale parking around $24 and a shuttle running an hour before opening through an hour after close, according to the official show page.
If you keep a dinghy at the Prince George Street dock, mark your calendar differently. That dock will be closed for the entire run from September 29 through October 18, with a temporary dinghy dock set up at the end of Shipwright Street for the duration, per the same event page. That's a three-week closure tucked inside a much longer construction timeline, and it's the kind of detail that only shows up if you're actually planning to tie up downtown this fall rather than just walk through it.
One more thing worth knowing if you've been avoiding the fence line on principle: posted construction hours run Monday through Saturday, roughly 7 a.m. to dusk, which leaves Sundays as the one day each week without an active crew on site. That makes the final day of each show, October 11 for powerboats and October 18 for sailboats, the closest thing to a construction-free look at the harbor this fall.
The Businesses Counting the Days Until October
Storm Brothers Ice Cream Factory has operated on Dock Street for nearly 50 years, having opened on October 29, 1976. Owner Sveinn Storm told Eye On Annapolis that sales fell by roughly $98,000 during the project's first year, and that by the middle of July 2026 the business was running another $98,000 behind that already-reduced year.
"I have to sell property. I have to sell assets to keep my business going until the end of this."
Storm owns his building outright, which is part of why he's staying, but ownership doesn't cover payroll or inventory on its own. The timing is almost cruel: his 50th anniversary lands eleven days after the Sailboat Show closes, right as the October crowds disappear and the fence line goes quiet again. This year, the two boat show weekends aren't a detour around his shop. They're close to the only reliable traffic he'll see before winter.
He's not alone. The mother-daughter owners of Annapolis Marine Art Gallery, a Dock Street fixture since 1978, have said the gallery plans to close its storefront by the end of the year, pointing to lost parking, fencing, and reduced foot traffic during construction. If that holds, this fall's boat shows are close to the gallery's last chance to draw a season's worth of visitors into the space it has occupied for nearly half a century.
What's New Alongside What's Long-Standing
Not everything downtown is contracting. The Admiral's Cup, a second location for the Fell's Point spot, is now open at 142 Dock Street in the old Stevens Hardware building, with live music seven nights a week on what the restaurant group calls the Cup's Stage. At the Annapolis Waterfront Hotel, two new dining concepts, Armada Waterfront Tequila Bar & Cantina and Marmo Italian Chophouse, were built to open this summer, with Armada seating 200 guests along the dock, according to the hotel's own dining page.
That mix, a business fighting to reach its 50th anniversary next to a restaurant that just opened its doors, is the actual texture of Dock Street this fall. It's not a simple story of decline, and it's not a simple story of renewal either. It's both, running side by side, and which way it tips for any given storefront may come down to whether the neighborhood treats these two show weekends as an inconvenience or an opportunity.
Two Weekends, Side by Side
| Powerboat Show | Sailboat Show | |
|---|---|---|
| Dates | October 8-11 | October 15-18 |
| Location | City Dock / Ego Alley | City Dock |
| Dinghy dock status | Closed (Prince George St.), use Shipwright St. | Closed (Prince George St.), use Shipwright St. |
| Best day for a construction-free walk | Sunday, Oct. 11 | Sunday, Oct. 18 |
| Worth a stop | Storm Brothers, ahead of its Oct. 29 anniversary | Annapolis Marine Art Gallery, possibly its final show season |
A Short List for the Two Weekends
- Park at Hillman Garage or ride the free Magenta Shuttle instead of circling for a Dock Street space that construction has likely removed.
- If you dinghy in, use the temporary dock at Shipwright Street through October 18. Prince George Street's dock is closed the entire span.
- Pick a Sunday if you want to see the harbor without an active work crew in view.
- Walk past Storm Brothers before October 29. The anniversary lands right after the crowds leave.
- Stop into the Marine Art Gallery while it's still on Dock Street. Nobody has confirmed how many more shows it has left.
The Bigger Point
Most years, the boat shows are a scheduling problem for people who already live here: extra traffic, fewer parking spots, a longer walk to the car. This year they're something closer to a stress test, for a construction project that won't finish until 2028 and for a stretch of small businesses trying to reach the other side of it. The shows bring the exact kind of dense, walking, spending crowd that Dock Street has been missing since the fencing went up. Whether that crowd actually helps depends on where people choose to spend twenty minutes and a few dollars between boats.
If the changes downtown have you wondering what they mean for property values along the waterfront, or if you're weighing a move to Annapolis while the harbor is mid-transformation, Jeff Lockard offers a complimentary home valuation and can walk you through what the City Dock project is likely to mean for waterfront and downtown-adjacent properties over the next two years.
