If your Eastport fall routine still assumes a walk to Ruth's Chris on Severn Avenue, a rope stretched across Spa Creek in early November, and a Fourth Street patio that might or might not be there next spring, your mental map is about six months out of date. Four separate stories broke between January and April of this year, and together they rearrange the peninsula's dining spine and its signature fall event.
Here is what a resident needs to know before October gets busy, without the tourist framing.
The Severn Avenue Corner Is About To Change Hands
The two-story building at Severn Avenue and Third Street has been Ruth's Chris for years, and before that it was Marmaduke's, the sailing bar that closed in the late 1990s. That's about to end. In April, Federal Realty Investment Trust confirmed that Ruth's Chris will take a 10,150-square-foot space at Annapolis Town Center in Parole, with a late fall 2026 opening, and franchisee Steve de Castro confirmed the Eastport location at 301 Severn Ave. will close as the new one comes online.
The immediate read is straightforward. Eastport loses a fine-dining anchor right next door to Lewnes' Steakhouse, which puts an unusual amount of pressure on a single block. Alderman Frank Thorp, who represents Eastport on the City Council, called the closure an opportunity as much as a loss, pointing at a great location with a great landlord. For anyone who walks to dinner on that corner, the question for late 2026 and early 2027 is who takes the building, not whether Eastport still has a steakhouse. Lewnes' handles that. What the block loses is the private-event capacity Ruth's Chris carried, and that's a hole worth watching.
Fourth Street's Patio Question, Finally Answered
Forward Brewing spent the winter in a fight most Eastport residents were following on Nextdoor whether they wanted to or not. Cam and Claire Bowdren opened the nanobrewery in 2020 with fewer than 30 indoor seats, pivoted to outdoor dining during the pandemic, and had been running roughly 90 seats on the old driveway and parking lot ever since. City rules formalized last year required a special exception, and a city planner initially recommended cutting the number to 45. In early February, after a nearly three-hour Board of Appeals hearing that drew 26 public speakers and hundreds of written comments, the board voted unanimously to grant 77 outdoor seats from March through November.
"Yes, 28 seats was our plan indoors. And then things changed, and outdoor dining became an option. It actually became a necessity during COVID, and then it stuck around. Now it's become our identity." — Cam Bowdren, co-owner, to The Baltimore Banner
Two things about that 77-seat number matter. First, it puts Forward on the same footing as Boatyard Bar & Grill, which also holds a 77-seat outdoor cap for part of the year. Second, the March-through-November window means the patio is open through Tug weekend and closes right after. If you host visiting family in December, that's not the plan anymore.
Boatyard Has A New Majority Owner
While the Forward Brewing hearings were dominating Eastport chatter, a quieter change went through at the corner of Severn and Fourth. Baltimore-based Atlas Restaurant Group, the same group opening Marmo and Armada at 80 Compromise Street in downtown Annapolis this summer, acquired a majority stake in Boatyard Bar & Grill. The award-winning crab cake is still the award-winning crab cake. The ownership behind it is not the same ownership that has run the place for twenty years.
For residents, the practical question is whether Boatyard's rhythms change: the sailor-heavy happy hour, the family-friendly Sunday brunch, the crowd mix that made it a genuine neighborhood room rather than a waterfront tourist stop. Atlas runs high-volume, high-design rooms downtown. Boatyard's identity has been the opposite of that. Worth watching through the fall and winter as menus and hours get revisited.
The Two Weekends That Reshape Your October
The Annapolis Boat Shows are on downtown's calendar, not Eastport's, but everyone on the peninsula lives with the parking overflow, the water traffic, and the Airbnb turnover. Two consecutive weekends this October are the ones to plan around:
| Event | Dates | Location | What it means on the peninsula |
|---|---|---|---|
| Annapolis Powerboat Show | Oct 8–11, 2026 | City Dock | First hit on parking; harbor filled with motor yachts, trawlers, center consoles |
| Annapolis Sailboat Show | Oct 15–18, 2026 | City Dock | Second and larger hit; floating docks lined with monohulls, catamarans, dinghies |
Preview Day for the Sailboat Show is October 9. That is the same day the Powerboat Show is still running. If you have contractors, deliveries, or medical appointments booked for those two weeks, look at your calendar now. Restaurant reservations on Fourth Street and Severn Avenue tighten dramatically, and the walk-in wait at Boatyard on a Sailboat Show Friday is not a walk-in wait. Reserve or reroute to Eastport Kitchen for the morning shift and O'Learys for a quieter evening.
The Tug Is On Second Street Now, And It's Staying There
The Maritime Republic of Eastport's annual Slaughter Across the Water — the tongue-in-cheek tug of war founded in 1998 after the Spa Creek Bridge closed for repair — traditionally stretched a 1,700-foot rope across the creek from Second Street to Susan Campbell Park at City Dock. That version has been on pause. Because of ongoing City Dock construction, the 2025 event moved entirely onto Second Street in Eastport, with teams squaring off on land instead of across the water. First tug at the crack o' noon, registration at 10 a.m., same charity mission that has raised over $500,000 for local nonprofits since inception.
For residents, this is a quality-of-life shift, not a downgrade. The rope-across-the-water version required Coast Guard and Harbormaster cooperation to close the harbor for two hours, and it pulled crowds to both sides of the creek simultaneously. The Second Street version concentrates everything into a walkable Eastport block party: food, music, teams from local businesses and neighborhood crews, and no need to cross the bridge. If you live within four blocks of Second and Chester, you no longer need to leave the neighborhood on Tug Saturday. If you live in the rest of Eastport, expect the streets around Second to be closed, and plan groceries the day before.
The Quieter Anchor: September At The Maritime Museum
Buried under all of that, one thing that hasn't changed is worth naming. The Annapolis Maritime Museum & Park at 723 Second Street continues its September Sunsets concert series at the Park Campus, with the 2026 season lineup building on the summer series. Concerts are free and donations are accepted, and there is no onsite parking, which the museum acknowledges directly in its guidance. For a peninsula that packs its October, the September concerts are the last low-key weekend before the boat shows land.
The Read For Residents
Put the four stories together and a pattern shows up. Eastport's dining spine is consolidating around its independents. Lewnes', O'Learys, Blackwall Hitch, Eastport Kitchen, Boatyard, and Forward Brewing are the names that anchor the peninsula going into 2027. The national franchise on Severn Avenue is on its way out. The neighborhood-founded brewery on Fourth Street is legally locked in for March through November. Boatyard's identity is the one to watch, because its new majority ownership is the variable, not the beloved local independents.
That is a different Eastport than the one a lot of long-time residents describe from memory. It's more locally owned on paper, more tightly clustered on Fourth Street, and its signature fall event has quietly become a walkable block party rather than a harbor spectacle. Whether that's an upgrade depends on how you use the neighborhood, but pretending nothing changed will get you a wait list at Lewnes' on the wrong Saturday.
If you have been in Eastport long enough to remember Marmaduke's, you already know how fast a corner can turn over. The Severn Avenue building will not sit empty for long. Watching who signs the next lease there is the local story of 2027.
When you are ready to talk about what any of this means for the value of a house between Chesapeake Avenue and Back Creek, or whether the ownership shifts on Fourth Street affect what you paid for walkability three years ago, Romeo Santos III and the Romeo Santos Group are a phone call away. Get your free home valuation and start the conversation with someone who actually walks these blocks.
