What happens to an Annapolis December when the holiday market and the downtown shops stop sharing a neighborhood?
This year we find out. The Annapolis Holiday Market is coming back for its fifth season, and for the first time it will be outside the historic district. It will be set up outdoors at Annapolis Mall, near West Street and Jennifer Road, on December 4 through 6 and December 11 through 13. Midnight Madness stays downtown on its usual Thursday nights. And the market's calendar never lands on a Thursday. The two biggest holiday shopping draws in town now take turns.
Four Decembers, Four Addresses
The market has moved before, but it always stayed close to downtown shops. Here is where it has been:
- 2022: Susan Campbell Park and the parking lot next to it at City Dock, Thursday, December 8 through Sunday, December 11. Eye On Annapolis later reported that the first year drew 45 artisans and 25,000 visitors over four days.
- 2023: 1 Dock Street, December 7 to 10, with more than 100 artisans and specialty food vendors.
- 2024: Back at the City Dock area, December 12 to 15, again with more than 100 artisans.
- 2025: Off City Dock because of construction, on the front lawn of St. John's College near College Avenue and St. John's Street. Eye On Annapolis described the site as about a block from the Calvert Street Parking Garage and a short walk from the shops on Maryland Avenue and State Circle.
Each of those sites put the market's chalets a few minutes' walk from downtown storefronts. Even in 2025, after City Dock construction pushed it off the waterfront, the market ended up beside the Maryland Avenue shops. You could browse the artisans and walk on to State Circle without moving the car.
The 2026 site ends that. City Dock construction is still underway, so the organizers moved the market to 1040 Annapolis Mall Road, near the former Sears Automotive Center. The City's August 25 construction update put the City Dock Park reopening as early as July 2027, so the waterfront won't be ready for this season.
What the Mall Site Changes
The new location gets easy access from Route 50, Route 450, and Route 178, plus free parking, public transportation access, and ADA accessibility, according to Eye On Annapolis. Admission is free. The same report expects about 150 artisans selling home décor, jewelry, pottery, glass, and art. The food lineup includes currywurst, raclette sandwiches, schnitzel, crab cakes, and a turkey cranberry brie grilled cheese.
The hours matter more than the menu. The organizer's site lists Fridays and Saturdays from 11 a.m. to 9 p.m. and Sundays from 11 a.m. to 7 p.m. That makes six days, all Friday through Sunday. The 2025 market opened on a Saturday and then ran Thursday through Sunday the next week. The 2026 schedule has no Thursday at all.
The market is at West Street and Jennifer Road. The Visit Annapolis Visitor Center, the hosting stop for Midnight Madness, is at 26 West Street. The street name is the same, but the two ends of the season are now a drive apart.
Downtown Keeps the Thursdays
Downtown's December has the same frame as before. Visit Annapolis lists Midnight Madness for Thursday, December 3, Thursday, December 10, and Thursday, December 17. It covers Main Street, West Street, Maryland Avenue, State Circle, Market Space, and Dock Street. Each participating business sets its own hours, so check your favorite shops before you go.
The Downtown Annapolis Partnership's Midnight Madness page describes the usual schedule. The first two Thursdays run from 4 p.m. to midnight and the third from 4 to 11 p.m. The same page lists free parking in the Calvert Street Garage from 6 p.m. to 6 a.m., $2 parking at Whitmore Garage from 4 p.m. to 6 a.m., two hours of free parking on commercial streets through ParkMobile, and a free Circulator or shuttle. Visit Annapolis points readers to annapolis.gov for the official, most current details, and that's the place to confirm this year's hours and parking.
The Visitor Center has something different each night from 5 to 8 p.m.:
- December 3: Free hot cocoa and a pop-up ornament shop from Pearl's Gallery.
- December 10: Free s'mores, plus massages and permanent jewelry from Even Keel Wellness Spa.
- December 17: S'mores again, with Eesh's Pieces selling cookies.
The City calendar also lists a separate "Midnight Madness on West Street" on December 17 from 6 to 10 p.m., running from Calvert Street to Church Circle. Visit Annapolis also lists Snowflake Alley, the lit-up stretch of Cabbage Alley, for December.
How the Two Calendars Interlock
Put the downtown dates next to the market dates and you get a weekly rhythm. A Thursday downtown comes first, then a market weekend at the mall, and in two cases a downtown event lands on the same day as the market.
| Date | Downtown Annapolis | Annapolis Mall |
|---|---|---|
| Sun., Nov. 29 | Grand Illumination near Market House and City Dock | |
| Thu., Dec. 3 | Midnight Madness, night one | |
| Fri., Dec. 4 | Market opens, 11 a.m. to 9 p.m. | |
| Sat., Dec. 5 | Market, 11 a.m. to 9 p.m. | |
| Sun., Dec. 6 | Chocolate Binge Festival, first block of West Street | Market, 11 a.m. to 7 p.m. |
| Thu., Dec. 10 | Midnight Madness, night two | |
| Fri., Dec. 11 | Market, 11 a.m. to 9 p.m. | |
| Sat., Dec. 12 | Eastport Yacht Club Lights Parade | Market, 11 a.m. to 9 p.m. |
| Sun., Dec. 13 | Market's final day, 11 a.m. to 7 p.m. | |
| Thu., Dec. 17 | Midnight Madness, final night |
Grand Illumination kicks things off on November 29 with the tree lighting near Market House and City Dock. Two market weekends follow.
The first weekend starts downtown on Thursday the 3rd with cocoa at the Visitor Center. The market opens across town the next morning. Sunday the 6th is the one day both ends of West Street are busy at once. The Chocolate Binge Festival takes over the first block of West Street downtown with desserts, warm drinks, and holiday crafts, and the market is open at the mall until 7 p.m. If you plan to do both, the market's earlier Sunday closing time sets the order.
The second weekend follows the same pattern, with Midnight Madness on the 10th and the market Friday through Sunday. Saturday the 12th is the busiest date on the calendar. The market is open until 9 p.m., and Visit Annapolis lists the Eastport Yacht Club Lights Parade the same day, with boats lit in nautical and Annapolitan themes in the harbor. The Santa Speedo Run is listed that day too. A daytime trip to the market leaves the evening open for the waterfront.
The third week belongs to downtown alone. The market closes on December 13, so the final Midnight Madness on the 17th, with the West Street block event from 6 to 10 p.m., is the last big shopping night of the season.
What Else Sits Near the Market
Annapolis Mall has added new stores and restaurants this year, Eye On Annapolis reports, so an afternoon at the market can include some shopping inside. The market is also being promoted alongside Lights on the Bay at Sandy Point State Park. That's a two-mile drive past 70 displays, running November 23 through January 3, 2027, with $5 off for military and first responders on December 21 and 27. For something closer to home on the same weekends, Visit Annapolis lists the North Pole Lights Walk at Willow Oak Flower & Herb Farm on select dates from November 28 through December 28.
The market and Midnight Madness used to sit within walking distance of each other. This year they take turns, three Thursdays downtown and six days at the mall. If you're working out where the holidays fit into a bigger plan, such as a move, a sale, or a new home with a view of the Lights Parade, Day Weitzman would be glad to talk it through. Request a confidential home valuation or private consultation, and plan your December around the calendar that's actually running this year.