Annapolis's Holidays Are Moving Away From City Dock Just as Dock Street Needs Them

The 2026 holiday calendar in Annapolis keeps its familiar dates, but several locations have changed. The Annapolis Holiday Market, now in its fifth year, is leaving downtown. It will run outdoors at Annapolis Mall near West Street and Jennifer Road on December 4 through 6 and December 11 through 13. Eye On Annapolis reported the reason in one line: ongoing construction at City Dock.

This is the market's second move in two years. Last year it set up on the front lawn of St. John's College. The move to the mall puts the biggest new December shopping event in Annapolis farther from the waterfront. Meanwhile, the businesses still open on Dock Street are going into the holidays after a hard construction year, and the City says real relief for that corridor arrives in steps between December and next summer.

The waterfront is still a work zone, on a published schedule

The City Dock Resilience Project is a flood-protection rebuild, and the City says it is running ahead of schedule. At an August 25 briefing, Mayor Jared Littmann laid out a revised timeline in a City of Annapolis press release:

• December 2026: The U.S. Naval Academy is expected to reopen Barry Gate, which the City says will restore foot traffic to the Dock Street business corridor.
• March 2027: The Ego Alley boardwalk reopens to pedestrians. Watermark returns to its berth at Susan Campbell Park, and boaters get back the Ego Alley slips.
• July 2027: City Dock Park opens, along with the Maritime Welcome Center, which will house the Harbormaster's headquarters and a City Dock visitor center.
• Summer 2027 to spring 2028: Phase Two, which the City has revised to limit closures on Upper Dock Street, the top of Ego Alley and Compromise Street.

That puts this holiday season between milestones. The City's Access Annapolis construction page, last updated in July 2026, lists lower Dock Street as closed between Craig Street and Susan Campbell Park and upper Dock Street as partially closed. The same page says Dock Street businesses remain open to pedestrians, with wayfinding signs and a customer pickup and drop-off area on upper Dock Street. The Barry Gate reopening is the first milestone that could make a difference before the holidays end. The City expects it in December, and its August 25 release is the latest public update on that date.

Who is still on Dock Street, and who is gone

In September, Eye On Annapolis reported on seven open Dock Street businesses taking part in a boat show ticket promotion: 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 losses have been just as visible. Bitty & Beau's Coffee at 124 Dock Street closed on September 13, more than six years after opening in Annapolis in February 2020, Eye On Annapolis reported. The same report said Blowfish Poké had suspended operations earlier this year with no reopening date, and that Annapolis Marine Art Gallery plans to close its Dock Street storefront at the end of 2026 and continue online.

The numbers behind those decisions are steep. In an August Eye On Annapolis story, the gallery's co-owner said revenue was down more than 70 percent. The owner of Storm Bros. said the shop's sales fell about $98,000 in the project's first year and another $98,000 by mid-July 2026.

Storm Bros. is responding by adding to its offerings. The shop opened on City Dock on October 29, 1976, and reaches 50 years on October 29 of this year. It announced a coffee, breakfast and pastry concept called Storm's a Brewing for the front of the shop. Several former Bitty & Beau's employees were expected to join, according to Eye On Annapolis. That report also passed along the owner's count of 39 frozen dessert businesses that opened and closed between the top of Main Street and the end of City Dock while Storm Bros. stayed. The shop targeted a late-September opening for the coffee counter, so check with the shop for current hours before planning a morning around it.

The 50th anniversary falls on a busy day. The City's fall events release brings Great Annapolis Pumpkins to Dock Street, with carving on October 29.

At the August briefing, Mayor Littmann addressed the business side directly:

"More than any grant or loan program can do, sustained sales will help these businesses survive and thrive."

The City published that remark in its August 25 release, along with a request that the public keep supporting downtown businesses.

December's calendar, sorted by distance from the fence

With that in mind, here is this year's calendar. Some events still land downtown, and one has left. The rest are elsewhere in the county.

Grand Illumination is co-presented by the City and the Downtown Annapolis Partnership, and the tree lighting is near Market House. That puts the season's opening event within walking distance of the stretch of Dock Street that is still open. The Partnership describes Midnight Madness as a downtown-wide evening of sales, refreshments and entertainment on Dock Street and the other commercial streets. That makes those three Thursdays the clearest built-in reason to walk the waterfront this December.

The Holiday Market at the mall has some practical advantages. Its organizers list free admission and free parking. Eye On Annapolis reports about 150 artisans, food such as currywurst, raclette sandwiches, schnitzel and crabcakes, and easy access from Route 50, Route 450 and Route 178. Its first weekend begins the day after the first Midnight Madness, so a Thursday evening downtown and a Saturday at the mall fit in the same weekend.

This year's Lights on the Bay is the 32nd edition, presented by the SPCA of Anne Arundel County. Before the drive-through season opens, its 2026 schedule lists Lights and Leashes walking nights on November 20, 21 and 22, followed by Military Monday discounts on December 7 and 21.

Getting to Dock Street without the boardwalk

The free Magenta Shuttle added a Dock Street stop in March. Riders can board at the Park Place, Knighton, Gott's or Mills Hillman garages, according to the City's February update. The City has also been running weekend electric carts between Mills Hillman Garage and Dock Street when the weather allows. Before construction started, it added 165 spaces to the rebuilt Mills Hillman Garage. That more than replaces the nearly 100 spaces removed at City Dock for flood-mitigation work.

Free holiday parking returns this season. The Visit Annapolis holiday events page says eligible downtown meters are free for the first three hours, for everyone, between Thanksgiving and New Year's Day, and it sends drivers to Annapolis Parking for details on which meters count. The Partnership's Midnight Madness page lists free evening parking at the Calvert Street Garage and two-hour street parking through ParkMobile.

Watching the Lights Parade from somewhere other than City Dock

The Eastport Yacht Club calls this year's event its 44th annual Lights Parade. It starts at 6:00 PM on Saturday, December 12. Visit Annapolis suggests watching from the city front, the Spa Creek Bridge, waterfront street ends, 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 parade viewers, apart from a stretch of promenade between Randall Street and Craig Street. It suggested the downtown street-end parks and arriving early. Construction has moved forward since then, so check the Access Annapolis maps the week of the parade before choosing a spot. The street ends near upper Dock Street put a warm drink at Storm's a Brewing or dinner at Dock Street Bar and Grill a short walk from the water.

If you live near downtown and want to talk through how the City Dock schedule, from Barry Gate this December to the park's opening next July, fits your own plans for the next couple of years, The Guzzone Group of Compass is glad to help. Start with a complimentary home strategy call.