This December, Annapolis Shops at the Mall and Celebrates at the Water

Construction fencing still runs along Dock Street, with directions printed on it, and the brick plaza around the Market House is still an active construction site. The city's latest schedule doesn't open City Dock Park until July 2027. That leaves one more holiday season downtown, and the organizers have split it between two locations.

Events that need the Market House or the harbor are staying downtown. The Annapolis Holiday Market, the biggest single shopping event of the season, has moved about two miles up West Street to a parking lot at Annapolis Mall. Most weekends you'll only need one of these spots. On two Saturdays in December you'll want both.

The Market Went Where the Parking Is

The Annapolis Holiday Market is in its fifth year. For 2026 it moves outdoors to Annapolis Mall, near the corner of West Street and Jennifer Road. Eye On Annapolis reported that the move is because of the ongoing City Dock construction. This is its second move in two years. In 2025 the market left City Dock for the lawn at St. John's College, as Eye On Annapolis covered last November.

Here are the details for 2026:

• Where: 1040 Annapolis Mall Road, outside the mall near the old Sears Automotive Center.
• When: December 4 to 6 and December 11 to 13. Friday and Saturday hours are 11 a.m. to 9 p.m., and Sunday hours are 11 a.m. to 7 p.m.
• Cost: Admission and parking are both free.
• Getting there: Organizers point to easy access from Route 50, Route 450 and Route 178, plus public transit and ADA accessibility.
• What's there: About 150 artisans selling pottery, glass, jewelry, home décor and art. The food list includes currywurst, raclette sandwiches, bratwurst with apple-braised sauerkraut, schnitzel, crabcakes, strudels and a turkey cranberry brie grilled cheese, plus hot chocolate, cider, wine and holiday liqueurs.

The tradeoff is simple. Free parking off Route 50 is easy to get to, but it isn't on the water. Everything that does need the water or the historic district stays downtown.

The Tree Still Goes Up at Market Space

Grand Illumination is on the City of Annapolis calendar for Sunday, November 29, from 3 to 5:30 p.m. at Market Space. It's run by the City with the Downtown Annapolis Partnership. The Partnership describes it as the annual tree lighting near the Market House, with activities starting at 3 p.m., and lists Fleet Street, Cornhill Street and Market Space among the road closures.

Market Space sits right at the edge of the construction zone, so the lighting is about as close to the fencing as the season gets. Two days earlier, on November 27, Historic Annapolis starts Christmas Traditions by Candlelight at the William Paca House. It runs on select dates from November 27 through December 26, according to Visit Annapolis's holiday listings.

Three Thursdays, and a Gate That Could Change Dock Street

Downtown shopping still happens, just on weeknights. Midnight Madness falls on Thursdays, December 3, 10 and 17. Its route covers Main Street, West Street, Maryland Avenue, State Circle, Market Space and Dock Street, and each shop sets its own hours and specials.

The Visitor Center at 26 West Street hosts a different local business each night from 5 to 8 p.m.:

Dock Street is the part of that route most affected by the construction. In its August 25 update, the City said the U.S. Naval Academy is expected to reopen Barry Gate in December 2026, "restoring foot traffic to the Dock Street business corridor." That's a forecast for next month, not a set date. If it holds, the Midnight Madness Thursdays are when Dock Street shops would first see more people walking by.

The City has also described what it's doing to help Dock Street during the work. Its August update listed a one-way traffic pattern, directions on the fencing, a Magenta Shuttle stop on Dock Street, and free weekend GEM cart rides from Mills Hillman Garage. The project is still on track in court as well. On October 19, the Appellate Court of Maryland upheld the Historic Preservation Commission's approval of the Maritime Welcome Center, and the City said construction continues.

Cabbage Alley, which Visit Annapolis calls Snowflake Alley, is lit with snowflakes through December. It's an easy photo stop between shops on any of the three Thursdays.

The Parade Still Needs the Harbor

No event is more tied to the water than this one. The 44th Eastport Yacht Club Lights Parade is Saturday, December 12, at 6 p.m. Lighted boats go through the harbor for about two hours. It started in 1981 and was named an Official Maryland Winter Celebration in 1988. The club's event listing says there are public places to watch, but access to the club grounds and clubhouse is limited to members who register.

The City's schedule doesn't reopen the Ego Alley boardwalk until March 2027, so the waterfront around the old dock will still be under construction on parade night. Last December gives a sense of how that plays out. Eye On Annapolis reported that for the 2025 parade, most of the usual viewing spots between Craig Street and Susan Campbell Park were closed. Part of the promenade between Randall Street and Craig Street stayed open.

Some other 2025 details are useful for planning. All of it describes last year, so treat it as a guide, not this year's plan:

1. Street ends on Spa Creek. The 2025 coverage listed Market, Shipwright and Revel Streets, Acton Cove, Southgate, Taney and Cheston Avenues, Lafayette Park and Monticello Avenue as good viewing spots on the downtown side, with parking restrictions posted nearby.
2. Pick one side of the bridge. The Eastport/Spa Creek Bridge drawspan was raised for much of the 2025 parade, so crossing between Eastport and downtown might not work once it starts.
3. Park outside the center. Last year Park Place Garage charged $5 after 5 p.m., and the free Magenta Shuttle ran into downtown. Mills, Hillman, Gott's and Knighton garages are on the shuttle route but filled up early.

The 2025 coverage also noted that some boats don't go up Ego Alley because they're too big to turn around safely, and not every boat goes past the bridge up Spa Creek.

Two Saturdays, Two Locations

Most of the season fits neatly in one place or the other. Two Saturdays don't.

December 5. The Holiday Market is open at the mall from 11 a.m. to 9 p.m. Downtown, Historic Annapolis is holding 1776: Yuletide in Revolutionary Annapolis. One way to do both is to visit the market at midday, when parking is easy, then head into the historic district.

December 12. The market is open at the mall until 9 p.m., and the Lights Parade starts on the water at 6 p.m. If you want both, go to the market first. Leaving the mall after dark means driving back toward the harbor just as parade traffic peaks.

Here's the full season in date order:

The City still says City Dock Park will open in July 2027, along with the Maritime Welcome Center. Its August schedule also includes a revised second phase, from summer 2027 through spring 2028, meant to limit closures on Upper Dock Street, the top of Ego Alley and Compromise Street.

If you're wondering what City Dock's next phase could mean for your street, your parking or your home's value, The DMV Dream Team can go over it with you, without any pressure. Melissa Davey follows these projects closely around Anne Arundel County and will give you a clear answer. Schedule a free consultation.