The Annapolis Holiday Market started in December 2022 as a downtown project with a specific job. It set up beside Susan Campbell Park at City Dock, and the Downtown Annapolis Partnership described it as a way to bring artisans into downtown and send visitors to the stores, restaurants and holiday events nearby.
In 2026, its fifth year, the market will run on the outdoor lot at Annapolis Mall near West Street and Jennifer Road. That's next to the former Sears Automotive Center, well beyond the brick streets it was created to serve. Downtown's own December traditions haven't moved. Grand Illumination, Midnight Madness, Snowflake Alley and the Chocolate Binge are all on the calendar at their usual addresses. If you live in the Historic District, the market is now the one holiday event this season you can't walk to.
Built to Feed Main Street
The market's original pitch was all about downtown. When it launched, Eye On Annapolis reported this goal from Erik Evans, executive director of the Downtown Annapolis Partnership:
"The market will allow local artisans to sell their products in downtown Annapolis, and hopefully, one day, some of these artisans will open their own storefront in downtown Annapolis."
That same 2022 announcement said the market would promote Midnight Madness, the Eastport Yacht Club Lights Parade and holiday parties at downtown restaurants. It also pointed visitors to free weekend parking at the Calvert Street Garage and a free circulator shuttle. From the start, the market was meant to work alongside the rest of the downtown holiday season.
Five Seasons on the Move
The market spent its first three seasons on the City Dock waterfront. Construction moved it off the dock in 2025 and out of downtown entirely in 2026.
- 2022: Next to Susan Campbell Park in the City Dock area, running Thursday through Sunday, December 8 to 11.
- 2023: At City Dock, 1 Dock Street.
- 2024: Back at Susan Campbell Park and the parking lot beside it, according to the City of Annapolis calendar.
- 2025: Off City Dock entirely while construction continued, on the front lawn of St. John's College near College Avenue and St. John's Street. That lawn is about a block from the Calvert Street Garage and a short walk from Maryland Avenue and State Circle.
- 2026: Annapolis Mall, 1040 Annapolis Mall Road, where the organizer is advertising free admission and free parking.
The St. John's College year still kept the market inside the historic core, within walking distance of Maryland Avenue. The 2026 location is a different kind of move. Eye On Annapolis lists its advantages as easy access from Route 50, Route 450 and Route 178, free parking, public transit and ADA accessibility. Those strengths serve someone driving in from across the county better than someone walking from Prince George Street.
The market keeps growing as it moves. Eye On Annapolis expects about 150 artisans, and the Visit Annapolis holiday guide lists 100. The food lineup includes currywurst, raclette sandwiches, schnitzel, crab cakes and strudel, along with hot chocolate, cider, wine and specialty holiday liquors. We found no organizer statement about whether the market will return downtown once the City Dock work is done.
What Still Happens on Foot
Downtown's own calendar hasn't gone anywhere. The Downtown Annapolis Partnership, the Inner West Street Association and the Visitor Center all organize events that stay on the streets they've always used.
| Event | 2026 Date | Location | Getting There from the Historic District |
|---|---|---|---|
| Maryland Avenue & State Circle Fall Festival | Sunday, October 18 | Maryland Avenue and State Circle | On foot |
| Great Annapolis Gingerbread Houses | November 22 – December 20 | Visitor Center, 26 West Street | On foot |
| Grand Illumination | Sunday, November 29, starting at 3 p.m. | Near Market House and City Dock | On foot |
| Midnight Madness | Thursdays, December 3, 10 and 17 | Main, West, Maryland Ave, State Circle, Market Space, Dock Street | On foot |
| Annapolis Holiday Market | December 4–6 and 11–13 | Annapolis Mall, West Street at Jennifer Road | By car or bus |
| Annapolis Chocolate Binge Festival | Sunday, December 6, 11 a.m. to 4 p.m. | First block of West Street | On foot |
| Eastport Yacht Club Lights Parade | Saturday, December 12 | Annapolis Harbor | On foot; check viewing spots |
The Downtown Annapolis Partnership's Midnight Madness page gives the hours as 4 p.m. to midnight on the first two Thursdays and 4 p.m. to 11 p.m. on the third. It describes a holiday light canopy over West Street and Maryland Avenue, a Christmas tree at Market Space, alpacas at the top of Main Street, and Snowflake Alley, the lit passage through Cabbage Alley from Main Street toward State Circle. That page doesn't carry a year, so treat the specific attractions as the usual format, not a confirmed 2026 lineup.
Thursday Downtown, Friday at the Mall
Midnight Madness falls on Thursday, December 3, and the Holiday Market opens the next day at the mall. The same thing happens the following week, with Midnight Madness on December 10 and the market reopening December 11. Both of those Thursday nights downtown are followed by a weekend of artisan shopping out on West Street at Jennifer Road.
In 2022, the market was set up to promote Midnight Madness and other downtown events "within a short stroll." This year you can do both on back-to-back days, but they're no longer one outing.
Parking is the other detail to plan around. The Partnership's Midnight Madness page lists free parking at the Calvert Street Garage, 19 St. Johns Street, from 6 p.m. to 6 a.m. It also lists $2 evening parking at the Whitmore Garage, 25 Clay Street, and two free hours at Hillman Garage for city residents. The page is undated. The City's dated parking release covers 2025, not 2026, so those offers reflect past practice until the City posts this year's terms.
The Waterfront Question Still Open
City Dock construction has already changed one other December tradition. Ahead of the 2025 Lights Parade, Eye On Annapolis reported that active work between Craig Street and Susan Campbell Park had closed off most of the usual waterfront viewing areas. The promenade from Randall Street to Craig Street stayed open.
Visit Annapolis lists the 2026 parade for December 12, and the Eastport Yacht Club is presenting it again. As of mid-October, no one has published a 2026 viewing advisory, so it's still unclear which stretches of the downtown waterfront will be open on parade night. The first half of the season, Grand Illumination near Market House, is still listed at its usual spot.
The Storefronts the Market Was Meant to Seed
The 2022 hope was that market artisans would someday open their own shops downtown. This year, Eye On Annapolis has reported a string of changes on those same downtown blocks.
- State Circle: Welcome Home Markets closed its State Circle shop after five years. According to Eye On Annapolis, founder Jenn Baker cited building repairs and an expiring lease. The business continues in Easton, Chestertown and online.
- Market Space: Blanca Flor Silver Jewelry announced in May that it would close its Market Space storefront and move online, Eye On Annapolis reported. Pearl Restaurant and the Ponche Tiki Bar upstairs closed at 26 Market Space. In an April report from Eye On Annapolis, the owners of Osteria 177 had taken over the space, and at that point the new concept hadn't been announced.
- West Street: 49 West Coffeehouse, Winebar & Gallery changed hands on September 1. As Eye On Annapolis reported, Brian and Sarah Cahalan passed it to Myriam Osorio McCormick, owner of McCormick Bakery & Chocolate Factory. She was expected to keep the staff, the live music and much of the menu, and she has renovations and a sweets counter planned.
Downtown's mix of shops and restaurants is changing in the same year the event created to support those storefronts sets up at the mall. The merchants still on these blocks have their next gathering soon. The Maryland Avenue & State Circle Business Association holds its Fall Festival on Sunday, October 18, on the same streets Welcome Home Markets left.
When you're figuring out which parts of December you can walk to and which ones need a car, it helps to know the blocks that well. Brian Jacobs at Annapolis Fine Property follows changes like these block by block across the Historic District, from Market Space storefronts to garage parking terms. If you're thinking about how a home's location fits the downtown calendar, Brian is glad to help. Get a positive, helpful partner and schedule a consultation.
