The Annapolis Holiday Market is in its fifth year, and City Dock construction has moved it for the second year running. Last December it went to St. John's College, as the Severna Park Voice reported. This year it moves out to Annapolis Mall, near the former Sears Automotive Center at West Street and Jennifer Road. Eye On Annapolis says to expect about 150 artisans outdoors over two weekends, December 4 through 6 and December 11 through 13. Visit Annapolis lists 100 artisans for the same market.
The new site puts the market at a property that changed owners this spring and has filled storefronts on a steady schedule since January. This December, the busiest holiday weekends in Annapolis will play out next to a mall that is still being rebuilt. The rebuild is part of what you'll walk past on the way to the craft booths.
Why the market moved, and where it landed
The reason is simple. Ongoing work at City Dock left no room for the market downtown, so organizers moved it to the mall for 2026. Eye On Annapolis lists the practical gains of the new site: easier access from Route 50, Route 450 and Route 178, free parking, public transportation access and ADA accessibility. Admission is still free.
Shoppers can buy straight from the artisans: home décor, jewelry, pottery, glass, art and crafts. The food list matters more than usual this year. Planned offerings include currywurst, raclette cheese sandwiches, bratwurst with apple-braised sauerkraut, schnitzel, crabcakes and a turkey cranberry brie grilled cheese, along with pretzels, strudels, holiday cookies, hot chocolate, apple cider, wine and specialty holiday liquors. The reason that list carries extra weight at this location comes up below.
The market is also part of the Visit Annapolis holiday calendar, which lists the same two weekends at the mall.
The property the market is moving onto
On May 6, 2026, Macerich announced it had bought Annapolis Mall for $272 million in total. That figure covers $260 million for the mall and $12 million, bought separately, for the vacant 13.1-acre Sears parcel next door. Macerich's announcement calls the Sears parcel optionality for future retail, mixed-use or other development. It names no proposal, tenant, approval or schedule, and nothing more specific has turned up since.
That's the background for the market's spot near the old Sears Automotive Center. The booths will stand beside the one corner of the property with no announced plan. Until a plan appears, two December weekends of artisans and hot cider are the most concrete thing scheduled on that side of the mall.
What has opened since January
The mall itself has added stores at a pace that's easy to lose track of. Here's the 2026 record in order, as far as public sources date it:
- First quarter: Urban Planet, DTLR, Talbots and an upgraded Hollister all opened, per Patch, which reported the openings without individual dates.
- January 12: World of Beer was set to open in an exterior building outside the mall, as the Capital Gazette reported. The mall's dining page now lists it as an exterior tenant.
- August 14: DICK'S House of Sport held its grand opening, with events running through August 16, according to Eye On Annapolis.
- Opening dates not published: UNIQLO, OFFLINE by Aerie, Aéropostale, Curmudgeon Books and Jolly Yolly Kids all appear as open on the mall's What's New page.
- October 9: Hobby Lobby opened a 50,000-square-foot store on the first floor, next to Onelife Fitness, per Patch.
Hobby Lobby opened three days ago. It's the newest store on the property, and it puts a large craft and décor store a short walk from a market built around handmade décor. Eye On Annapolis notes that the new stores and dining give market visitors more places to shop before or after.
Every 2026 opening on that list is retail except one. World of Beer is the only new food or drink spot, and it sits outside the main building. The market's vendor list fills that gap. For two weekends, the mall gets a temporary food court of schnitzel, raclette and crabcakes that its permanent tenant list doesn't include yet.
What is still marked "coming soon"
The mall's What's New page lists more openings ahead. Some have firm months, some have already missed their targets, and some won't arrive until 2027.
November 2026 targets. Abercrombie & Fitch and the Tesla dealership and service center are both listed for November. If both hold, they could open in the weeks just before the market's first weekend. Abercrombie's November timing matches what Eye On Annapolis reported in April.
Announced, target passed. Pop Mart and Miss A were both listed for September 2026 and still show as coming soon. Jack & Jones still shows a summer 2026 target. In July, What Now reported that Pop Mart was on track for September. As of mid-October, no public source confirms that any of these three has opened. Miss A's own store locator still lists Annapolis Mall as coming soon.
2027. Dave & Buster's is listed for 2027. A larger Lululemon is also planned for 2027, according to Eye On Annapolis. Dave & Buster's is the only new sit-down dining and entertainment venue on the mall's announced list, so the food gap the market fills this year won't close before next year.
How December splits between West Street and the harbor
The market moved, but downtown's own traditions are still on the calendar. The Visit Annapolis holiday listings put Midnight Madness on three Thursdays: December 3, 10 and 17. The Downtown Annapolis Partnership describes the usual hours as 4 p.m. to midnight on the first two Thursdays and 4 to 11 p.m. on the third. The Eastport Yacht Club's 44th annual Lights Parade is set for Saturday, December 12, at 6 p.m. The club describes dozens of lit boats moving through Annapolis Harbor over two hours.
Visit Annapolis also lists the Annapolis Chocolate Binge Festival on Sunday, December 6, on the first block of West Street downtown. Put the dates together and the two locations mostly take turns:
- Thursday, December 3: The first Midnight Madness, downtown.
- Friday through Sunday, December 4 to 6: The market's first weekend, at the mall, with the Chocolate Binge Festival downtown on Sunday.
- Thursday, December 10: The second Midnight Madness, downtown.
- Friday through Sunday, December 11 to 13: The market's second weekend, at the mall.
- Saturday, December 12, 6 p.m.: The Lights Parade on Annapolis Harbor, during the market's final weekend.
- Thursday, December 17: The last Midnight Madness, ending at 11 p.m.
December 6 and December 12 are the two days when both ends of West Street have something on the calendar. The market's daily hours for 2026 haven't been published in the sources we reviewed, so it's best to check the Annapolis Holiday Market site before planning a day at the mall followed by an evening at the harbor. Eye On Annapolis also lists Lights on the Bay, historic tours, seasonal performances and downtown dining as options to pair with a market visit.
So downtown keeps its Thursday nights and the parade, and the market's two weekends belong to West Street this year. They'll take place next to a mall that has opened stores since January, expects at least two more by November and still has 13.1 acres with no announced plan.
West Street has changed a lot in 2026: a new owner, a long list of openings and an open question about the Sears parcel. If you own a home nearby and want to know how changes like these figure into what buyers will pay, Erica Baker can walk you through a current valuation built on what's actually happening along the corridor. Start with "What's Your Property Worth?" and we'll take it from there.
