Downtown Annapolis's Holidays Run on the City Dock Reopening Schedule This Year
October 22, 2026
October 22, 2026
Once the boat-show docks and tents come out, City Dock becomes a construction site again. The construction then sets the timing of downtown Annapolis's holiday season. The tree lighting, three Midnight Madness Thursdays and the Lights Parade all happen this year on a waterfront that's partly fenced off. For Dock Street, the most consequential December date may be a gate reopening. The City expects the U.S. Naval Academy to reopen Barry Gate in December 2026, a step it says will restore "foot traffic to the Dock Street business corridor."
That puts the holiday calendar and the reopening schedule on the same few blocks. Reading them together is the easiest way to plan a downtown December this year.
The Annapolis Boat Shows kept their October dates this year but changed the setup. The traditional A and B tents came off City Dock, and the footprint spread onto Compromise and Randall Streets. The City gave show crews until close of business Friday, October 23, to clear out. Its September 11 City Dock newsletter said the site returns to Whiting-Turner at the end of October so construction can resume. The newsletter also said lending the site to the shows had been built into the plan and doesn't move the overall schedule.
The street layout the holidays will use is the one locals have had for most of the year. Dock Street was narrowed to one-way traffic running west to east. That direction came from a City survey of the Dock Street businesses. Public Works restriped the street for head-in parking and added a loading zone. The City's construction page shows lower Dock Street closed between Craig Street and Susan Campbell Park, plus a partial closure of upper Dock Street between Craig and Randall Streets, scheduled through May 2027. Crews work Monday through Saturday, 7 a.m. to dusk.
The fences along Ego Alley also hold "An Exhibition of Sight & Sound." The walkable gallery pairs Chesapeake Bay landscapes by Maryland photographers with portraits by local artists. AND Creative and the Annapolis Symphony Orchestra put it together at no cost to the City.
Storm Bros. Ice Cream Factory opened at City Dock on October 29, 1976, so the shop reaches its 50th anniversary this Thursday, October 29. Eye On Annapolis reported that owner Sveinn Storm counts 39 frozen dessert businesses that have opened and closed between the top of Main Street and the end of City Dock in that time.
The shop is also adjusting to the season and the construction. In the same report, Storm described plans for "Storm's a Brewing," a coffee, breakfast and pastry counter at the front of the shop, meant to draw customers earlier in the day and across more of the year. "So, necessity is the mother of invention," he said, as quoted by Eye On Annapolis. The planned opening window was September 21 to 25, and the article noted that City permitting would likely be required.
An ice cream shop adding a morning coffee counter in late fall is one sign of how Dock Street businesses are working through the construction. In September, a joint promotion with the boat shows was aimed at drawing residents and visitors to the businesses operating behind the fence. Eye On Annapolis named the participants: The Big Cheese and Sammy's Deli, The Admiral's Cup, Dock Street Bar and Grill, Pip's Dock Street Dogs, Storm Brothers Ice Cream Factory, Sofi's Crepes and Latitude 38. The Admiral's Cup opened in February 2026 at 142 Dock Street, in the former Stevens Hardware building. That makes it one of the few places on the street to open during construction rather than before it.
These are the businesses that would gain the most when the Prince George Street side of the block opens up again.
The Navy's construction near Barry Gate is a flood-protection project of its own. The Naval District Washington announcement describes tearing out the existing wall and building a new flood wall along the Academy fence from Barry Gate to Gate 0, with a detachable flood barrier adjusted at Barry Gate itself. It gave the expected completion as Winter 2026. Until then, Naval Academy Tourism sends visitors to the Randall Street entrance. The City's August 25 timeline, its most recent public forecast, puts the reopening in December. That means it could land anywhere in this list:
Through the whole stretch, the Gingerbread Houses display at the Visitor Center runs from November 21 through January 6.
A December reopening would put the gate back in use during the three Thursdays when Dock Street is part of the official Midnight Madness route. It's still a forecast, so the honest planning assumption is that some of those evenings will have it and some won't.
The parking math favors the garage. The City estimates about 99 spaces were lost on upper and lower Dock Street. It added 165 spaces at Mills Hillman Garage, which it describes as a three-minute walk.
The free Magenta Shuttle was rerouted to stop on Dock Street and at Prince George Street by Barry Gate. That second stop becomes more useful once the gate reopens. On weekends, a free open-air GEM cart loops between Mills Hillman and Dock Street. For the boat shows, the City pointed drivers to Park Place, Knighton, Gotts and Mills Hillman garages with a shuttle connection. That's a good model for a Midnight Madness Thursday.
The Lights Parade is where construction affects the evening most, because the usual viewing spots are on the water. Eastport Yacht Club's calendar says more details are coming. It also notes that the clubhouse and grounds are open only to members who register for wristbands during the event, while public viewing spots remain available.
Until the 2026 guidance comes out, last December's setup is the best reference. In 2025, Eye On Annapolis reported that most usual waterfront viewing areas were closed by City Dock construction. A section of promenade between Randall Street at the top of Ego Alley and Craig Street stayed open. Watermark Cruises ran a viewing boat at the end of Prince George Street, and some larger boats skipped Ego Alley because they couldn't safely make the turnaround. The same report listed street-end spots along Spa Creek on the downtown side. These included Market, Shipwright and Revel Streets, Acton Cove, Southgate, Taney and Cheston Avenues, Lafayette Park and Monticello Avenue. It also noted that the Eastport/Spa Creek Bridge drawspan was raised for much of the parade, so spectators generally stayed on whichever side they started. The construction footprint is largely the same this year, so those street ends are a reasonable first plan.
The City's August 25 release reported the project on budget and ahead of schedule, with projected reopening dates after Barry Gate:
The City notes that the full flood-protection benefit depends on finishing every phase, so some construction will remain after the park opens. Next spring's Ego Alley boardwalk and next summer's park will be easier to plan around than this December, which has only the gate to look forward to.
If you're watching how the City Dock reopenings change downtown, or want to talk through what they could mean for homes near the water, Michelle L Blanchard would be glad to compare notes on the neighborhood with you. Let's Connect.
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