More than 400 boats arrive at City Dock this week for the Annapolis Powerboat Show, which runs October 8 through 11. On Thursday evening, after the opening day, there is a free block party on Market Space. A short walk from the docks, the coffee shop at 124 Dock Street has been closed for nearly a month.
Both of those things come from the same construction project. Dock Street's storefronts have not lost their appeal. Fencing, fewer parking spaces and a closed Naval Academy gate have cut off many of the ways people used to walk in. The fixes in place this fall all reroute people, and the first big reopening on the city's calendar is also a route. Barry Gate is due back in December, more than half a year before the new City Dock Park.
Three Dark Storefronts on One Block
On the stretch between 110 and 124 Dock Street, three businesses have closed or announced closings in 2026, and each gave its own reason.
Bitty & Beau's Coffee at 124 Dock Street closed in mid-September. Eye On Annapolis reported the last day as September 13 and pointed to slower foot traffic during construction plus a decision about the lease. Maryland Bay News cited a company-confirmed date of September 14 and said the company's stated reason was that the lease expired.
Two doors down at 122 Dock Street, Blowfish Poké has suspended operations and has not given a reopening date. Annapolis Marine Art Gallery at 110 Dock Street plans to close its physical store at the end of 2026 and continue online. Maryland Bay News treats these as separate cases with different reasons. The gallery has been the most direct about construction. In May, it said reduced foot traffic and a revenue drop of more than 70% followed the removal of parking and the spread of construction fencing.
The biggest restaurant loss in town this summer happened somewhere else. O'Learys Seafood planned its final service for August 2 after more than 40 years and cited the loss of its lease. Maryland Bay News noted that O'Learys sits across Spa Creek, away from Dock Street, and has no apparent connection to the City Dock project.
Two Closed Routes In
Construction removed about 99 parking spaces from upper and lower Dock Street, and the street now runs one way, west to east. The second closure gets less attention. Barry Gate, the Naval Academy entrance at the Prince George Street end of the corridor, is closed while the academy works on the Prince George Street wall. The academy's visitor information directs walkers headed to Gate 1 to use the Randall Street entrance. The academy's project is separate from the city's, and the city mentions it when describing problems Dock Street merchants have raised about access.
Nobody has measured how much of the traffic loss comes from the gate and how much from the fencing. The city's own announcement shows how much the gate matters. Its August 25 update said the academy is expected to reopen Barry Gate in December, "restoring foot traffic to the Dock Street business corridor."
The city's fixes this year have mostly been ways to bring people back to the block. Here is how to get there this month:
- Park at Mills Hillman Garage. The rebuilt garage gained 165 spaces, more than the roughly 99 removed from Dock Street, and the city calls it a three-minute walk.
- Take the free GEM cart on weekends. Since early summer, open-air electric carts have looped between Mills Hillman and Dock Street on weekends, weather permitting.
- Take the Magenta Shuttle. In March, the city rerouted the free downtown shuttle to add a stop at Dock Street and Prince George Street, at Barry Gate. The ads inside the bus are now 16 linear feet of Dock Street businesses, each shown with its name, logo and street address.
- Use Upper Dock Street for pickups and drop-offs. The city's construction page says Dock Street businesses can still be reached, with customer pickup and drop-off along Upper Dock Street.
On foot, the fence along Ego Alley now holds "An Exhibition of Sight & Sound." It pairs Chesapeake Bay nature photographs by Maryland photographers with portraits by local artists, and AND Creative and the Annapolis Symphony Orchestra installed it at no cost to the city.
The city has also been direct about how far its help goes. In its business-support update, it said a city the size of Annapolis "simply do[es] not have the financial capacity to make private businesses whole" for revenue lost to construction, and it asked the public to shop downtown.
October's Events Bring Crowds to the Corridor
Big events are the strongest draw Dock Street has this year, and organizers have planned around the fence.
The two fall boat shows normally use exhibit tents A and B on City Dock. This year both tents are out because of construction. Other tents are larger, and parts of the shows extend farther onto Compromise and Randall streets, with new gathering areas spread through the grounds. The Annapolis Sailboat Show follows on October 15 through 18. Randall Street is the same street the Naval Academy now points walkers to, so this month the show and the detour around Barry Gate overlap.
The boat shows have tried to help Dock Street before. In March, Annapolis Boat Shows worked with 10 Dock Street businesses on a promotion that gave shoppers who made a purchase that month free tickets to the April spring sailboat show.
After the boats leave, more October events reach the corridor:
- Great Annapolis Pumpkins starts October 10. Displays go up at the Visitors Center, Hopkins Plaza, Dock Street and Maryland Avenue, and in Eastport for the first time. Artists carve the pumpkins on October 29, and the displays stay up through November 2.
- Maryland Avenue Fall Festival returns October 18, a short walk up from the dock.
- Art @ the Park at Quiet Waters Park runs October 17 and 18 from 10 a.m. to 4 p.m., with regional artists, demonstrations, music and food trucks. It falls on the same weekend as the sailboat show and works as a plan for the afternoon.
Who's Staying, and How They're Adjusting
The businesses still open on Dock Street have changed what they sell to match the people walking past.
Storm Bros. Ice Cream Factory has served ice cream at City Dock for nearly 50 years. In August, its owner described falling sales and said he was determined to keep the shop open. In September, Storm Bros. announced Storm's a Brewing, a coffee, breakfast and pastry counter at the front of the ice cream shop. It aimed to open between September 21 and 25, and several former Bitty & Beau's employees were expected to work there. Local reporting has not yet said whether it opened on schedule, so check before you plan a morning around it. If it did open, the block's coffee counter moved a few doors and kept some of the same staff.
One business opened during the construction. Admiral's Cup started serving at 142 Dock Street in February 2026, in the former Stevens Hardware building. It is a restaurant and bar with live music, wings, handhelds and bar bites, and when it opened it said shareable pizzas were coming soon.
A January list of Dock Street businesses open during construction included Armadillo's, Dock Street Bar & Grill, Eagle Souvenir, Latitude 38, Pip's Dock Street Dogs and Sofi's Crepes. At least two businesses on that list have closed or announced a closing since January, so check hours before you walk over.
What Reopens First
On August 25, Mayor Jared Littmann said the City Dock project was on budget and ahead of schedule, and he released a revised timeline.
| Target | What reopens | What it changes on Dock Street |
|---|---|---|
| December 2026 | Barry Gate, reopened by the U.S. Naval Academy | Walkers can come straight in from Prince George Street again |
| March 2027 | Ego Alley boardwalk | Pedestrians are back on the boardwalk, Watermark returns to its berth at Susan Campbell Park, and boaters can use the Ego Alley slips again |
| July 2027 | City Dock Park and the Maritime Welcome Center | A new park plus the harbormaster headquarters and the city and county visitor center |
| Summer 2027 to spring 2028 | Revised Phase Two | Closures limited along Upper Dock Street, the top of Ego Alley and Compromise Street |
These are targets, and none of them has happened yet. The order still tells you something. The first two reopenings restore ways to walk in, a gate and then a boardwalk, and both come before the park and visitor center everyone has been waiting for. If the December date holds, Dock Street gets its Prince George Street entrance back in time for the holidays. The waterfront park would follow about seven months later, in July 2027.
At the Anthony Friedman Team of Northrop Realty, we follow changes like this across Central Maryland because a reopened gate or a new boardwalk changes how a neighborhood works long before it changes a map. If you're near the Annapolis waterfront and want to know how the City Dock timeline could affect your plans, contact us and we'll talk it through.
