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Dock Street's Busiest Month Lands in Its Hardest Year

A charcoal-painted residential door with an ivory fanlight surround beside a sash window in weathered red brick, above limestone steps and a brick approach.

"I own my building," Sveinn Storm told Eye On Annapolis in August. "So come hell or high water, I'll just continue to sell assets so that I can preserve it. I'm not walking away from this."

Storm runs Storm Bros. Ice Cream Factory on City Dock. He said sales fell about $98,000 in the first year of the current construction project. By mid-July 2026 the shop was another $98,000 behind that already-lower year. Those numbers explain this October better than any boat show preview. The Annapolis Powerboat Show (October 8–11) and the United States Sailboat Show (October 15–18) are coming back to City Dock. Construction barriers and reduced waterfront access are still in place there. This year, the crowds the shows bring are being treated as a lifeline for the businesses that stayed.

The Shows Started Selling Dock Street Before They Sold Boats

In mid-September, the Annapolis Boat Shows ran a ticket promotion through Dock Street storefronts. From September 14 through 18, anyone who walked into a participating business could scan a QR code for 50% off Preview Day and General Admission tickets to either show. Eye On Annapolis reported it was the biggest discount offered on this year's fall shows, and the only way to get it was to stop by a business on Dock Street.

Mary Ewenson, president of the Annapolis Boat Shows, called the City Dock Resiliency Project "a great investment in the future" that will help with nuisance flooding for years. "However, we know businesses are navigating the challenges of construction today," she said, "so we want to help bring people downtown and encourage them to support those businesses that are open and welcoming visitors." The fall push follows a spring run of the same idea. Eye On Annapolis covered the Spring Sailboat Show teaming up with Dock Street businesses back in March.

Mayor Jared Littmann put it more plainly at an August 25 press conference and construction tour. "More than any grant or loan program can do, sustained sales will help these businesses survive and thrive," he said. He also acknowledged that "some, not all, of the Dock Street businesses are struggling."

Getting Downtown Between October 5 and 21

Supporting the strip depends on being able to reach it. Here's the show-period setup from the City of Annapolis logistics notice.

  • Restriction window: Expect show-related road closures, detours and parking restrictions from October 5 through 21. Setup began September 30, the changeover between the two shows runs October 11–15, and move-out continues through October 23.
  • District 1 permit-only streets: Prince George Street from Craig to East, Randall Street from Prince George to King George, East Street from Prince George to King George, Green Street, Newman Street and St. Mary's Street.
  • No parking at all: Prince George Street from Craig Street to the docks.
  • Garages and shuttles: The four City garages are open to showgoers. The free Magenta Shuttle loops between the garages and downtown about every 10 minutes, and the City also lists a free stadium shuttle.

Some of this is already in place because of the construction. The Magenta Shuttle has a stop on Dock Street, weekend electric carts run from Mills Hillman Garage, and the City added loading zones and wayfinding signs. The City says Mills Hillman's 165 added spaces outnumber the roughly 100 Dock Street spaces that construction removed. The Magenta Shuttle's Dock Street stop sits at Prince George Street, by Barry Gate.

Who Was Still Serving in Mid-September

Seven businesses signed on to the September ticket promotion, which means all seven were operating as of mid-September:

  • The Big Cheese and Sammy's Deli
  • The Admiral's Cup
  • Dock Street Bar and Grill
  • Pip's Dock Street Dogs
  • Storm Brothers Ice Cream Factory
  • Sofi's Crepes
  • Latitude 38

The list of departures has been growing all year. Blowfish Poké at 122 Dock Street suspended operations early in 2026 and hasn't announced a reopening date. Bitty & Beau's Coffee at 124 Dock Street announced September 13 as its last day. Accounts of why differ. Naptown Scoop reported that the company pointed to its lease ending. Eye On Annapolis said lower foot traffic during construction and a decision not to renew likely both played a part.

The Annapolis Marine Art Gallery at 110 Dock Street announced in May that it will close its storefront at the end of 2026 and move to online-only sales. Co-owner Samantha Wilkerson said foot traffic dropped and revenue fell by more than 70%. That means the gallery is open for both boat shows and the holiday season, and then it closes its doors.

"We have watched four nearby businesses announce their closing," Storm said in September. "We don't want Storm Bros on the City's extinction list."

October 29, at the Foot of the Dock

Storm Bros. opened on October 29, 1976, which makes this October 29 its 50th anniversary. Storm has seen plenty of competition come and go. By his count, 39 frozen dessert businesses have opened and closed between the top of Main Street and the end of City Dock since he started. He also lived through earlier rounds of City Dock work in 2007–2008 and in 2015–2016. Local coverage we reviewed hasn't announced any anniversary event.

The same day, local artists will carve the Great Annapolis Pumpkins at four downtown spots: Hopkins Plaza, the Visitor Center, the Opera House on Maryland Avenue and Dock Street. The pumpkins stay on display through November 2. So a 50-year-old ice cream shop and a freshly carved giant pumpkin will share the same stretch of Dock Street that week.

Storm is also trying something new for the slower months. "Storm's a Brewing," a coffee, breakfast and pastry counter at the front of the shop, was set to open between September 21 and 25, with several former Bitty & Beau's employees expected to join. We couldn't find local reporting confirming it opened on schedule, so check before you plan a morning around it.

The Calendar From Move-Out to Barry Gate

The shows finish move-out on October 23. After that, the next big boost for foot traffic on Dock Street is the reopening of Barry Gate at the Naval Academy, which the City expects in December 2026. The City describes that reopening as "restoring foot traffic to the Dock Street business corridor." The weeks between those two dates still have plenty going on downtown:

  1. October 21: Last of the City's regular Wednesday Dinner Under the Stars nights. West Street is closed between Church Circle and Calvert Street from 4:30 to 11 p.m.
  2. October 24: Navy hosts North Texas at 3:30 p.m. at Navy-Marine Corps Memorial Stadium. Its other October home game, against Tulsa, falls on October 10, during the Powerboat Show.
  3. October 25 to November 1: The Scarecrow Stroll along West Street, Maryland Avenue and Main Street, hosted by the Inner West Street Association with the Maryland Avenue and State Circle Association and the Downtown Annapolis Partnership.
  4. October 29: Great Pumpkin carving day and the Storm Bros. anniversary.
  5. October 31: A Motown finale for West Street Dinner Under the Stars, 6 to 9 p.m., according to Naptown Scoop.
  6. November 1: First Sunday Arts Festival on West and Calvert Streets, 11 a.m. to 5 p.m.
  7. December 2026: Barry Gate is expected to reopen.

Two other changes this year are a short walk from the dock. Atlas Restaurant Group opened Marmo Italian Chophouse and Armada Dockside Cantina on July 16 inside the Annapolis Waterfront Hotel at 80 Compromise Street. And on September 1, 49 West at 49 West Street passed from founders Brian and Sarah Cahalan to Myriam Osorio McCormick of McCormick Bakery & Chocolate Factory. She plans to keep the staff and the live music and add chocolate and pastries.

What the Next Year Looks Like

The City's August timeline runs well past this fall. The Ego Alley boardwalk is set to reopen to pedestrians in March 2027, which also lets Watermark return to its berth at Susan Campbell Park. City Dock Park and the Maritime Welcome Center, which will house the Harbormaster and a visitor center, are targeted for July 2027. A smaller second phase follows from summer 2027 to spring 2028, with limited closures on Upper Dock Street, the top of Ego Alley and Compromise Street. The City also says tidal flooding has already dropped significantly. Full protection from rain-driven flooding won't arrive until every phase is done.

Storm doesn't expect the finished park to bring customers back right away. "The amount of customers that we're losing right now, it's gonna take years before we get all that back," he said.

VSells & Associates follows downtown Annapolis closely, from boat show parking zones to which storefronts are still open on Dock Street. If you're curious how this kind of local detail shapes what your home is worth, get your free home valuation and we'll walk you through it.

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