The tree lighting on November 29 takes place near Market House, at the top of a waterfront that has been a work zone since November 2025. Under the City's current schedule, lower Dock Street is closed between Craig Street and Susan Campbell Park, and upper Dock Street is partly closed between Craig and Randall Streets. That work is projected to continue through May 2027. This is the second holiday season with the fence up, and it changes where the season actually happens. Most of downtown's December now plays out on West Street, along the Thursday-night shuttle routes, and at the street ends on both sides of Spa Creek. Dock Street is still open for business, but you'll have to plan a visit there on purpose.
What the fence covers on a December evening
Construction runs Monday through Saturday, from 7 a.m. to dusk. The project site says Dock Street businesses remain open, with signs pointing customers to them and pickup and drop-off on Upper Dock Street. That schedule leaves out Sundays, which is when the Grand Illumination and the Chocolate Binge Festival fall, and by early December dusk arrives well before Midnight Madness winds down.
The City has added a few ways to reach the closed-off block. The free Magenta Shuttle now has a Dock Street stop. Weekend GEM carts run between Mills-Hillman Garage and Dock Street when the weather allows. The rebuilt Mills-Hillman Garage added 165 spaces. If you're driving in for any event on this calendar, that garage and the carts are the closest way to the waterfront end of downtown.
West Street carries the season's busiest Sunday
Most years the waterfront is the center of the holiday season. This year the first block of West Street gets a full Sunday of its own. The Annapolis Chocolate Binge Festival runs Sunday, December 6, from 11 a.m. to 4 p.m. at 60 West Street, with chocolate vendors, entertainment and holiday shopping. Visit Annapolis adds warm drinks, family activities and holiday arts and crafts to the festival lineup.
The block has seen several changes since summer. Eye On Annapolis reported that 49 West, the coffeehouse, wine bar and gallery, changed hands on September 1. The new owner is Myriam Osorio McCormick of McCormick Bakery & Chocolate Factory. Her plans include a sweets counter with McCormick chocolates, pastries and desserts. The music room and the staff were expected to stay. A chocolatier now runs a shop on the same street as the chocolate festival.
Two doors up, Leo Annapolis at 212 West Street is expanding into 208 West Street, the former All The Rage Vintage space. The new room will add seating and space for private events.
Earlier in the season, the Annapolis Gingerbread Houses go on display at the Visitors Center from November 21 through January 6, 2027. Visitors can vote for their favorite. In December, Cabbage Alley becomes Snowflake Alley, lit with twinkling snowflakes.
The tree, then three Thursdays
The Grand Illumination is Sunday, November 29, near Market House and City Dock. The Downtown Annapolis Partnership presents it with the City of Annapolis and lists the celebration as starting at 3 p.m. It falls on a Sunday, so the construction crews won't be working that afternoon.
Four days later, Midnight Madness starts, with downtown shops staying open late on three consecutive Thursdays. Here are the hours from the Downtown Annapolis Partnership's Midnight Madness page:
| Thursday | Hours |
|---|---|
| December 3 | 4 p.m. to midnight |
| December 10 | 4 p.m. to midnight |
| December 17 | 4 p.m. to 11 p.m. |
Getting there and parking matter as much as the shopping. The Partnership's event page lists:
- Free parking at the Calvert Street Garage from 6 p.m. to 6 a.m.
- Two free hours of parking on commercial streets through ParkMobile
- Free Circulator and shuttle service
The Partnership's transportation page says the Circulator runs until 12:30 a.m. on Midnight Madness nights, and the Ten-Minute Trolley runs on those evenings too, weather permitting. For daytime trips, Visit Annapolis says eligible meters are free for the first three hours from Thanksgiving through New Year's Day. With the Circulator and the Magenta Shuttle's Dock Street stop, you can park at Calvert Street and still reach the waterfront end of downtown without walking around the work zone.
Saturday the 12th belongs to the street ends
The Eastport Yacht Club's 44th Lights Parade starts at 6 p.m. on Saturday, December 12. It's a two-hour parade of lit-up boats through Annapolis Harbor. The organizer's spectator guide still lists City Dock, but it warns that Campbell Park may not be open because of the construction. Susan Campbell Park sits at the end of the closed stretch of Dock Street, so the street ends listed lower in the guide matter more this year.
The guide's main viewing spots:
- Spa Creek Bridge. You can see boats above and below the bridge as they pass through. The guide warns that cold or windy nights there are especially brisk, and the bridge closes from time to time between 5:30 and 8 p.m.
- City Dock. Boats pass twice, first as they parade in and again one by one as they head back out.
- Ego Alley. The closest look at the boats and their crews.
- The U.S. Naval Academy seawall. A long, open stretch along Spa Creek. The guide says to check ahead on Naval Academy security rules.
- The walkway in front of Annapolis City Marina in Eastport.
The guide also lists street ends and parks on both sides of the water: 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, Second, Third and Fourth Streets in Eastport. Spots near you are fine for watching on foot. They also keep you clear of the City Dock crowd and the bridge closures.
The spectator page also lists a Harbor Queen viewing party from 5 to 8 p.m. at Watermark Yacht Basin, 1 Prince George Street, with music and a cash bar. The Santa Speedo Run is the same day.
Dock Street is worth the detour
Dock Street needs the visitors more than any other part of this calendar, and it has been losing businesses. Eye On Annapolis reported that Bitty & Beau's Coffee at 124 Dock Street closed on September 13. The shop opened in February 2020 and employed people with intellectual and developmental disabilities.
Next door, Storm Bros. Ice Cream Factory turned 50 on October 29. It opened on City Dock in 1976. In September, owner Sveinn C. Storm announced plans for Storm's a Brewing, a coffee, breakfast and pastry counter at the front of the shop. The idea is to bring in customers earlier in the day and for more of the year. Several former Bitty & Beau's employees were expected to join it. He explained the move in a Facebook post that Eye On Annapolis quoted:
"So, necessity is the mother of invention."
December could bring more people back to the block. In an August 25 press release, Mayor Jared Littmann said the project is on budget and ahead of schedule. The U.S. Naval Academy is expected to reopen Barry Gate in December 2026, which should bring foot traffic back to the Dock Street business corridor. The release projects these next milestones:
- March 2027: The Ego Alley boardwalk reopens to pedestrians. Watermark returns to its berth at Susan Campbell Park, and boaters get access to the Ego Alley slips again.
- July 2027: City Dock Park and the Maritime Welcome Center open.
- Summer 2027 to spring 2028: A revised Phase Two with more limited closures along Upper Dock Street, the top of Ego Alley and Compromise Street.
If those dates hold, this is the last holiday season Ego Alley's boardwalk will be closed. In the meantime, the Magenta Shuttle stop and the weekend GEM carts from Mills-Hillman bring you right to the businesses still open behind the fence. A Midnight Madness stop or a walk down before the parade is an easy way to visit them.
If you'd like to talk through what the City Dock project means for homes near downtown and Eastport, I'm glad to do that over coffee on Dock Street. Colleen Smith works with buyers and sellers across Annapolis and the waterfront. Let's Connect.
