The Annapolis Holiday Market is coming back for its fifth year in December, but not downtown. Eye On Annapolis reported on October 24 that the market will be held outdoors at Annapolis Mall, near West Street and Jennifer Road, because of ongoing construction at City Dock. It runs December 4 through 6 and December 11 through 13, with free parking at the outdoor site near the former Sears Automotive Center.

So the season downtown has less going on at the water and more along the streets. The tree lighting, the Thursday late nights and the photo stops are all still here. They just sit a few blocks uphill from the fence, on Market Space, West Street, Main Street and Maryland Avenue. One date could still shift things back toward the water before New Year's: the Naval Academy's Barry Gate, which the City expects to reopen sometime in December.

The Season Starts at Market Space

The City's calendar lists Grand Illumination for Sunday, November 29, from 3:00 to 5:30 p.m. at Market Space. Visit Annapolis describes it as the annual tree lighting near Market House and City Dock.

That puts the season's opening event right at the edge of the construction zone. People will gather on the brick at Market Space with the fenced site in view. The lighting takes place in late afternoon, and by the time it ends the Sunday crowd is already within a few minutes' walk of Main Street's restaurants.

Three Thursdays Across Six Streets

Midnight Madness has more room than any other downtown event this season. Visit Annapolis lists three Thursdays: December 3, 10 and 17, 2026. The event covers Main Street, West Street, Maryland Avenue, State Circle, Market Space and Dock Street, decorated with lights, trees, garlands, snowflakes and bows. The Downtown Annapolis Partnership gives the hours as 4 p.m. to midnight on the first two Thursdays and 4 to 11 p.m. on the third.

Dock Street is on that list. In a normal year it would be one more stop along the route. This year it's the street closest to the work, and it has the most to gain from foot traffic on those three nights. Visit Annapolis notes that each business sets its own hours, specials and activities, so it's worth checking with a favorite shop before heading out.

Here's how the full stretch lines up, from the tree lighting through the last late night:

The market weekends and the Midnight Madness Thursdays fall on alternating days, so both fit into the same two weeks.

The Visitor Center at 26 West Street Anchors the Evenings

On all three Midnight Madness nights, the Visitor Center at 26 West Street is open from 5:00 to 8:00 p.m., with a different program each time:

1. December 3: complimentary hot cocoa and a holiday ornament pop-up from Pearl's Gallery.
2. December 10: complimentary s'mores, plus free massages and permanent jewelry from Even Keel Wellness Spa.
3. December 17: s'mores again, with Eesh's Pieces selling cookies.

The Visitor Center sits at the West Street end of the event, well away from the construction. Starting there and walking down toward Church Circle and Main Street sets the evening up from the uphill end. Farther along West Street, Eye On Annapolis reported on October 23 that Leo Annapolis is expanding into the storefront next door at 208 West Street, the former All the Rage Vintage space, to add seating and a private-event area.

Back down the hill, Visit Annapolis lists Snowflake Alley for December 2026: Cabbage Alley lit with twinkling snowflakes, which Visit Annapolis bills as a favorite photo backdrop.

What the Fence Still Holds Through Winter

The City's August 25 construction update laid out what's coming. In December 2026, the U.S. Naval Academy is expected to reopen Barry Gate, which would bring foot traffic back to the Dock Street business corridor. In March 2027, the boardwalk along Ego Alley reopens to pedestrians, and Watermark returns to its berth at Susan Campbell Park. In July 2027, City Dock Park and the Maritime Welcome Center are scheduled to open.

That makes the 2026 holidays the last winter with the boardwalk closed, and possibly the first weeks with Barry Gate open again. The City has given the gate's reopening as a month, not a specific day. If it opens before the December 17 Midnight Madness, the corridor between the Academy and Dock Street could see foot traffic it hasn't had all year.

Construction continued into the fall. The project's October 20 update says work went on after the Appellate Court affirmed the approval process for the Maritime Welcome Center. The fence itself now has things to look at. In August the City described a 180-foot outdoor art display on the construction fencing along the waterfront promenade at the top of Ego Alley, facing the alley, along with custom wayfinding banners and decorative wraps on the fencing along Upper Dock Street.

At the August briefing, Mayor Jared Littmann said some, though not all, Dock Street businesses were struggling, and he asked the public to keep shopping downtown. As quoted in the City's release:

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

Those three Thursdays in December are the stretch of the calendar where that kind of support adds up fastest.

Getting Down the Hill Without the City Dock Lot

The construction took nearly 100 parking spaces at City Dock. In its August release, the City said it had made up for them ahead of time by adding 165 spaces to the rebuilt Mills Hillman Garage. The City's August project FAQ puts the garage about 500 feet from Market Space, a short walk to the Grand Illumination crowd.

As of that August update, the City also listed these supports for the Dock Street corridor:

• The free Magenta Shuttle was rerouted in March to add a dedicated Dock Street stop, and all of its in-bus advertising now goes to Dock Street businesses.
• In early summer, electric carts began running from Mills Hillman Garage to Dock Street on weekends, weather permitting.
• Parking spaces on City Dock were reconfigured, and loading zones were created for deliveries and customers.

The City's August release describes these as business-support measures, not as a holiday schedule. Anyone planning to use the carts on a December weekend should check the City's current service before relying on them. Visit Annapolis points to annapolis.gov as the official source for up-to-date event information.

December 12 Brings the Harbor Back In

The Eastport Yacht Club Lights Parade gives the season its one night centered on the water. Visit Annapolis lists it for Saturday, December 12, 2026. The club's calendar says more parade details are coming and that access to the clubhouse and grounds is limited to members, so anyone watching from the public side should plan accordingly.

The parade falls on a Saturday between the second and third Midnight Madness Thursdays, during the second Holiday Market weekend, and in the same month the City expects Barry Gate to reopen. No other date on the 2026 calendar stacks that many of the season's events into one weekend.

We've been watching City Dock's construction schedule as closely as our neighbors, and for anyone who owns or is thinking about a home within walking distance of Market Space, how this season goes says a lot about the next few years downtown. If you'd like to talk about how the City Dock timeline fits your own plans, The Tower Team is at 209 Main Street, along the Midnight Madness route. Work With Us.