The free Magenta Shuttle has a stop on Dock Street at Prince George's Street, right at Barry Gate. The City added it in March after Dock Street business owners asked for help bringing customers to a corridor cut off by construction. The stop sits beside the Naval Academy gate, which has been closed while City Dock is rebuilt.
According to the City's own timeline, the Naval Academy is expected to reopen Barry Gate in December 2026. The City says that will restore foot traffic to the Dock Street business corridor. December is also when downtown's holiday calendar runs through Dock Street three Thursday nights in a row. If the forecast holds, this will be the first holiday season since heavy construction began in which Dock Street has its usual December crowds and its route to the Academy at the same time. City Dock Park will still be fenced off in the middle of it all.
The Fence Stays Up Through the Holidays
In an August 25 announcement, Mayor Jared Littmann said the City Dock project was on budget and ahead of schedule, and the City laid out revised milestones.
| Milestone | City's forecast |
|---|---|
| Barry Gate reopens, restoring foot traffic to Dock Street | December 2026 |
| Ego Alley boardwalk reopens to pedestrians; Watermark returns to its berth at Susan Campbell Park | March 2027 |
| City Dock Park opens; Maritime Welcome Center grand opening | July 2027 |
| Revised Phase Two, with limited closures on Upper Dock Street, the top of Ego Alley and Compromise Street | Summer 2027 to spring 2028 |
Only the first of those dates falls during this year's holiday season. The rest come after the decorations are down. The Maritime Welcome Center will house the Annapolis Harbormaster and a City Dock visitor center, and in October the City reported that the Appellate Court had affirmed the center's approval. Eye On Annapolis reported that the later work will no longer require a large closure of Upper Dock Street. Instead, crews will work in smaller sections around Ego Alley.
The City says Dock Street businesses stay open to customers throughout construction. Some of the work around the businesses is already done. At the Kunta Kinte–Alex Haley Memorial, where business owners had raised concerns about standing water, the Department of Public Works reset 1,500 bricks to grade to improve drainage and replaced the benches.
November 29 Starts the Season at Market Space
The season opens a few steps uphill from the fence. The City's calendar lists Grand Illumination for Sunday, November 29, from 3 to 5:30 p.m. at Market Space, the Sunday after Thanksgiving. Visit Annapolis describes it as the annual tree lighting near the Market House and City Dock. Downtown Annapolis Partnership co-hosts the event with the City.
Grand Illumination is held at Market Space, outside the construction area, so the season's first event stays out of the work zone. The next events come back to the water.
Three Thursdays That Still End on Dock Street
Midnight Madness falls on Thursday, December 3, Thursday, December 10 and Thursday, December 17. Downtown Annapolis Partnership, which presents the event, sets its hours at 4 p.m. to midnight on the first two Thursdays and 4 to 11 p.m. on the third. The route covers Main Street, West Street, Maryland Avenue, State Circle, Market Space and Dock Street. Dock Street is still on the route this year. Each business sets its own hours and specials, so Visit Annapolis suggests checking with individual shops before you go.
At the West Street end, the Visitor Center at 26 West Street is open from 5 to 8 p.m. on all three nights, with a different program each time:
- December 3: free hot cocoa and a Pearl's Gallery pop-up selling ornaments
- December 10: free s'mores, plus free massages and permanent jewelry from Even Keel Wellness Spa
- December 17: s'mores again, with Eesh's Pieces selling cookies
Two of the Madness nights fall in the month the City expects Barry Gate to reopen. Mayor Littmann made a related point in the City's August press release, speaking about the businesses beside the construction:
"More than any grant or loan program can do, sustained sales will help these businesses survive and thrive."
What's New Along the Route Since Last December
Downtown has a few new names since last year's Madness nights. Crème de la Crème, the Virginia home-goods boutique founded by Tara and Ben Wegdam, held a grand opening in late October at 8 Francis Street. It is the company's sixth location, after its Middleburg flagship and stores in Leesburg, Alexandria, Richmond and Frederick. The shop sells tableware, linens, fragrances and handmade goods. Its regular Thursday hours, according to the Baltimore Business Journal, are 10 a.m. to 7 p.m. Francis Street runs between Main Street and State Circle, both on the Madness route.
On West Street, LEO Annapolis has announced that it will expand into the shop next door at 208 West Street, the former All the Rage Vintage space, according to Eye On Annapolis. The extra space will be used for more seating and private events.
At City Dock, Storm Bros. Ice Cream Factory, which opened on October 29, 1976, has planned Storm's a Brewing, a coffee, breakfast and pastry counter at the front of the shop. Eye On Annapolis covered the plan in a September report on how construction has affected downtown businesses.
December 12 Moves the Crowd to the Harbor
The 44th annual Eastport Yacht Club Lights Parade is set for Saturday, December 12, at 6 p.m. That is two days after the second Madness Thursday and five days before the last. As usual it falls on the second Saturday of December, with boats covered in lights spending about two hours on a route through Annapolis Harbor. The parade started in 1981, when EYC members Jim and Shirley Langer, who lived on their boat in Spa Creek, strung Christmas lights on its rigging and cruised the harbor singing carols. By 1988 it had been named an Official Maryland Winter Celebration.
City Dock Park is not scheduled to open until July 2027, so viewing spots away from the dock matter more this year. Visit Annapolis suggests the Annapolis city front, the Spa Creek Bridge, the end of any downtown street that meets the water, and the pocket parks in Eastport and Murray Hill. With the Lights Parade between two Madness nights, the week of December 10 to 12 is the busiest stretch of the season: a late shopping night downtown on Thursday, then the harbor on Saturday.
| Date | Event | Where |
|---|---|---|
| Sun., Nov. 29, 3 to 5:30 p.m. | Grand Illumination | Market Space |
| Thu., Dec. 3, 4 p.m. to midnight | Midnight Madness | Main, West, Maryland Ave., State Circle, Market Space, Dock |
| Thu., Dec. 10, 4 p.m. to midnight | Midnight Madness | Same route |
| Sat., Dec. 12, 6 p.m. | EYC Lights Parade | Annapolis Harbor |
| Thu., Dec. 17, 4 to 11 p.m. | Midnight Madness | Same route |
Getting Down to Dock Street
The shuttle stop and cart service the City added for Dock Street this year are worth knowing before the holidays. The Magenta Shuttle stops on Dock Street at Prince George's Street, by Barry Gate. On weekends, weather permitting, the City has been running a free open-air electric cart in a loop between Mills-Hillman Garage and Dock Street. Holiday parking rates, event shuttles and road closures are set each season and posted on annapolis.gov. Last year's release went up on November 10. The City's City Dock site carries construction updates as the work continues.
If you're thinking about how City Dock's reopening schedule fits with your own plans for a home in Annapolis or elsewhere in Anne Arundel County, Teresa Burton can walk you through what the coming milestones may mean for your property's value. Request a Free Home Valuation, and enjoy the lights.
