The Annapolis Holiday Market is back for its fifth year, but not downtown. Because of ongoing construction at City Dock, the 2026 market will be held outdoors at Annapolis Mall near West Street and Jennifer Road. That one move changes how the whole season is laid out. The weekend shopping now happens at the mall. Downtown's Thursday nights now center on the first block of West Street. The waterfront still hosts its two big nights, Grand Illumination and the Lights Parade, but parts of it are behind construction fencing.
Put the dates on a calendar and you can see the pattern. For the first two weeks of December, each Thursday night downtown is followed by a Friday-to-Sunday weekend at the mall. The third week has only the Thursday.
| Date | Day | Event | Where |
|---|---|---|---|
| Nov 29 | Sunday | Grand Illumination | Near Market House and City Dock |
| Dec 3 | Thursday | Midnight Madness | Downtown |
| Dec 4–6 | Friday–Sunday | Annapolis Holiday Market | Annapolis Mall, 1040 Annapolis Mall Road |
| Dec 6 | Sunday | Chocolate Binge Festival | First block of West Street |
| Dec 10 | Thursday | Midnight Madness and Midnight Madness on West | Downtown; West Street & Church Circle |
| Dec 11–13 | Friday–Sunday | Annapolis Holiday Market | Annapolis Mall |
| Dec 12 | Saturday | EYC Lights Parade | Annapolis Harbor and Spa Creek |
| Dec 17 | Thursday | Midnight Madness and Midnight Madness on West | Downtown; West Street & Church Circle |
The market moved to Jennifer Road, and the weekends went with it
The Annapolis Holiday Market lists two weekends: December 4 to 6 and December 11 to 13, outdoors at 1040 Annapolis Mall Road. The Arts Council of Anne Arundel County lists the hours as 11 a.m. to 9 p.m. on Friday and Saturday and 11 a.m. to 7 p.m. on Sunday. One news report gave the first weekend as December 3 to 5. The organizer's page says December 4 to 6, so check that page before you plan around the opening day.
According to Eye On Annapolis, the market will set up near the former Sears Automotive Center. It expects about 150 artisans selling home décor, jewelry, pottery, glass, art and crafts. Food vendors plan currywurst, raclette cheese sandwiches, bratwurst with apple-braised sauerkraut, schnitzel, crabcakes and turkey cranberry brie grilled cheese. Drinks include hot chocolate, cider, wine and holiday liquors. Admission is free.
The new site has some practical advantages over a construction zone. The same report notes easier access from Route 50, Route 450 and Route 178, free parking, public transportation access and ADA accessibility. That convenience comes at a cost to downtown, though. Both market weekends are now away from the historic district. Downtown's weekly holiday draw falls on Thursdays instead.
Thursdays now center on West Street
Midnight Madness, the late-night shopping event presented by the Downtown Annapolis Partnership, runs December 3, 10 and 17. DAP's standing schedule runs the first two Thursdays from 4 p.m. to midnight and the third from 4 p.m. to 11 p.m. That page is not dated for 2026, but the hours match this year's Thursdays.
On two of those three Thursdays, West Street adds an event of its own. The Inner West Street Association is holding Midnight Madness on West, an outdoor holiday market at West Street and Church Circle, on December 10 from 6 to 10 p.m. and again on December 17 starting at 6 p.m. The listing promises festive decor, live entertainment, art vendors and a human hamster ball run on the first block of West Street.
The same association runs the Chocolate Binge Festival on Sunday, December 6, from 11 a.m. to 4 p.m. on the first block of West Street. That falls on the closing day of the market's first weekend, so a Sunday of shopping could easily cover both ends of West Street.
This year the block has one more chocolate connection. Myriam Osorio McCormick, owner of McCormick Bakery & Chocolate Factory, bought 49 West Coffeehouse, Winebar & Gallery effective September 1, 2026. The plan adds a sweets counter with McCormick Chocolates, pastries and desserts, and keeps the live music room open. Eye On Annapolis suggested the change could bring more attention to this year's Chocolate Binge Festival. The counter was announced as planned, so don't count on it being open by December 6.
City Dock keeps its two big nights, behind fencing
Grand Illumination is still planned for the Market House area. Visit Annapolis lists it for Sunday, November 29, with the tree lighting near Market House and City Dock. The Downtown Annapolis Partnership presents it with the City of Annapolis. Neither listing mentions any change in location or format because of construction.
The 44th annual EYC Lights Parade is Saturday, December 12, at 6 p.m. The trickier question is where to stand. The organizers still list City Dock as a favorite viewing spot, since viewers there see each boat twice: once as the fleet parades in and again as each boat heads back out into the harbor. Right under that entry, the spectator page adds this warning:
PLEASE NOTE CAMPBELL PARK MAY NOT BE ACCESSIBLE DUE TO CONSTRUCTION
The City's own schedule makes the problem clear. The Ego Alley boardwalk is not due to reopen to pedestrians until March 2027, and City Dock Park until July 2027. Both dates fall after parade night. The EYC spectator page also lists these alternatives:
- Spa Creek Bridge, which EYC calls the best spot on a warm or still night. The bridge will close periodically between 5:30 and 8 p.m.
- The U.S. Naval Academy seawall along Spa Creek, with a long, open view. Check the Academy's security rules ahead of time.
- Aboard Harbor Queen at the Watermark Yacht Basin, 1 Prince George Street, from 5 to 8 p.m., with music and a cash bar.
- The walkway in front of Annapolis City Marina in Eastport.
- Street ends at the harbor and Spa Creek, including Market, Shipwright and Revel Streets, Acton Cove, Southgate, Taney and Cheston Avenues, Lafayette Park, Monticello Avenue, Primrose Road at Truxtun Park, Burnside Street, and First through Fourth Streets.
Two things were still missing as of early October. The only route map posted is labeled 2025, and the 2026 announcement gives no rain date. If you plan to watch from a street end, check eyclightsparade.org again in December.
The December date that isn't on any holiday calendar
One more milestone could change downtown in the middle of the season. Mayor Jared Littmann's August 25, 2026 update on City Dock said the U.S. Naval Academy is expected to reopen Barry Gate in December 2026, "restoring foot traffic to the Dock Street business corridor." No specific day was announced. If the gate opens before the parade, the Dock Street blocks next to the Academy would get their walk-in traffic back in the busiest weeks of the downtown year.
The same update noted that the City says some Dock Street businesses are struggling. The mayor asked the public to keep supporting them: "More than any grant or loan program can do, sustained sales will help these businesses survive and thrive." The City also points out that the construction has already greatly reduced tidal flooding at City Dock, and that full protection from rain flooding will come once every phase is finished. So the fencing at Grand Illumination comes from the same project that should make the waterfront drier for future seasons.
Getting between the two ends
The mall and Church Circle sit at opposite ends of West Street, so getting around matters more this year. The Downtown Annapolis Partnership lists these options:
- The free Circulator runs between West Street and City Dock until 11 p.m. on weekdays and Saturdays and until 8 p.m. on Sundays. On Midnight Madness nights it runs until 12:30 a.m.
- The Magenta Shuttle is free and was rerouted this year to add a dedicated Dock Street stop, according to the City's August update.
- Mills-Hillman Garage gained 165 spaces when it was rebuilt before construction started, according to the City.
Holiday meter rules for 2026 are still unconfirmed. Visit Annapolis says eligible meters are free for the first three hours between Thanksgiving and New Year's Day. The Downtown Annapolis Partnership describes two free hours at commercial-street meters through ParkMobile from Black Friday to New Year's Day. The most recent City press release on holiday parking we found is from November 2025. Until a 2026 version comes out, plan on two hours and treat any extra time as a bonus. At the mall end, parking is free.
If you're expecting family for the Lights Parade or planning a Thursday at Midnight Madness this year, The PCS Home Team is happy to help you work out where to stand, where to park and what's open around City Dock. Many of our clients are new to Annapolis, so we keep track of what changes in town from one season to the next, including during construction. Make Your Move Easy — Schedule a Free Consultation.
