Downtown Annapolis Holidays 2026: City Dock and Barry Gate
October 29, 2026
October 29, 2026
The boat shows have packed up, and City Dock is going back to the contractor. By the City's September notice, Whiting Turner was set to resume construction once the show returned the site at the end of October. That means a second holiday season with a fenced waterfront downtown. This year, though, one change lands partway through the season. The U.S. Naval Academy expects to reopen Barry Gate in December 2026. The City's August 25 announcement says the reopening will restore foot traffic to the Dock Street business corridor.
The water won't be the way into Dock Street this holiday season. People will come in from the Academy end and from the parking garage. Once you see how those two routes work, planning a Grand Illumination evening or a Midnight Madness Thursday gets simpler.
The City's revised schedule leaves no doubt about the water's edge this winter. The boardwalk along Ego Alley reopens to pedestrians in March 2027. Watermark can then return to its berth at Susan Campbell Park, and boaters get the Ego Alley slips back. City Dock Park and the Maritime Welcome Center, which will house the Harbormaster headquarters and a City Dock visitor center, are targeted for a grand opening in July 2027. The project's construction page lists lower Dock Street between Craig Street and Susan Campbell Park as closed through May 2027, with a partial closure on upper Dock Street between Craig and Randall Streets.
All of those dates are targets. The City says the project is on budget and ahead of schedule, and Mayor Jared Littmann has said the FEMA funding, grants and bond allocations already in place cover the rest of the work. A revised Phase Two runs from summer 2027 to spring 2028. It's planned to limit closures on upper Dock Street, at the top of Ego Alley and on Compromise Street.
That matters for the Eastport Yacht Club Lights Parade on December 12. Visit Annapolis lists the usual viewing spots: the city front, the Spa Creek Bridge, downtown street ends at the water, and the pocket parks in Eastport and Murray Hill. Last December, Eye on Annapolis reported that most of the City Dock waterfront was closed to viewers. A stretch of promenade and the other street ends were still open. The boardwalk won't reopen until March, so the bridge and the Eastport side are the safest plan for parade night this year.
Barry Gate is the Naval Academy's pedestrian entrance at Craig Street and Prince George Street. The work around it is a separate Navy project from the City's. In July 2025, Naval Support Activity Annapolis awarded a $2.6 million contract for a new flood wall along Prince George Street. The wall replaces the old one from Barry Gate to Gate 0 and adds a detachable flood barrier at Barry Gate itself.
The gate opens straight onto the corner where Dock Street's businesses begin. Once it reopens, people walking out of the Yard will come out right at the top of the street again.
Arriving by car works differently now. About 99 on-street spaces on upper and lower Dock Street were lost to the project. To make up for them, the City added 165 spaces at Mills Hillman Garage, which it describes as a three-minute walk away. Dock Street itself now runs one way, west to east, because the merchants asked to keep that direction. The parking that's left was restriped for head-in spaces, and there's a new loading zone.
You don't have to walk from the car, either. The City rerouted the free Magenta Shuttle to stop on Dock Street and at Prince George Street by Barry Gate. On weekends, a free open-air GEM cart loops between Mills Hillman and Dock Street. The shuttle's Barry Gate stop already serves that corner, so the December reopening adds Academy foot traffic to a corner the shuttle already covers.
The walk past the fence is worth slowing down for. The City has hung a walkable gallery, "An Exhibition of Sight & Sound," along the Ego Alley fencing. It pairs Chesapeake Bay landscapes by Maryland photographers with portraits by local artists, and AND Creative and the Annapolis Symphony Orchestra produced it at no cost to the City.
The Annapolis Boat Shows' September promotion listed these businesses as open during construction. The addresses come from the City's Dock Street directory.
Business | Address | What to know |
|---|---|---|
The Admiral's Cup | 142 Dock Street | Opened in February 2026 in the former Stevens Hardware building |
Dock Street Bar & Grill | 136 Dock Street | Listed open in the September promotion |
Storm Brothers Ice Cream Factory | 130 Dock Street | Announced a coffee, breakfast and pastry counter |
Pip's Dock Street Dogs | 118 Dock Street | Listed open in the September promotion |
Sofi's Crepes | 1 Craig Street | On the Craig Street corner by Barry Gate |
Latitude 38 Waterfront | 12 Dock Street | Listed open in the September promotion |
The Admiral's Cup is the newest name on that list. Naptown Scoop reported in February that it was opening in the old Stevens Hardware building at 142 Dock Street. Storm Bros. announced a front-of-store concept called Storm's a Brewing, with coffee, breakfast and pastries. According to Eye on Annapolis, the planned opening window was September 21 to 25. The Big Cheese and Sammy's Deli also appeared in the boat-show promotions for Dock Street-area businesses.
The list is shorter than it was. In August, Eye on Annapolis reported that Bitty & Beau's Coffee at 124 Dock Street was expected to close on September 13. The same report said Blowfish Poké Hawaiian Grill at 122 Dock Street had suspended operations earlier in the year, and that Annapolis Marine Art Gallery at 110 Dock Street plans to close its physical gallery at the end of 2026 and move online. That makes this the gallery's last holiday season with a storefront on Dock Street.
Access is the thread running through the August reporting. Dock Street business owners interviewed by The Banner and Eye on Annapolis pointed to the construction fencing, limited waterfront access and parking as the pressures on their business. A reopened Barry Gate puts a pedestrian entrance back at the top of their block.
Barry Gate's reopening is the one item on this list with no fixed day, so it may arrive between events:
Visit Annapolis also points to free holiday parking at various locations between Thanksgiving and New Year's Day. Before you go, check the City of Annapolis for this year's terms, because last year's offers may not carry over. Mills Hillman's added spaces, the Magenta Shuttle and the weekend GEM cart all cover the gap between the garage and the shops.
If you've put off a Dock Street visit since the fencing went up, the December 10 and December 17 Midnight Madness evenings are your best chance to walk the length of the street. If the reopening comes on schedule, Barry Gate will be open by then, and the Admiral's Cup, Storm Bros. and Sofi's Crepes will all be on the route.
Questions about how the City Dock work affects a downtown Annapolis home, a slip, or a future sale or purchase near the water? The Lucas Knott Laye Team follows these milestones closely and is glad to talk through what the 2027 reopenings could mean for your plans. Contact Us.
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