Ruth's Chris Steak House has anchored the corner of Severn Avenue since 1996. Sometime this fall it will close for good, trading its Eastport storefront for 10,150 square feet across two levels at Annapolis Town Center. Back on Eastport's own Sixth Street, a men's clothier named after the neighborhood's own nickname for itself already opened its doors back in May, months before that closure ever made the news. Both moves are about the same thing: what a business needs from this particular stretch of peninsula, and what it doesn't get.
That's the thread worth pulling on this season. One long-running tenant is leaving because it outgrew what Eastport can offer. One new tenant arrived earlier this year because Eastport was the only place its founders wanted to be. And layered on top of both, the roads connecting Eastport to the rest of Annapolis are being rebuilt around a two-week stretch of boat shows that has already started reshaping the neighborhood's edges this month.
The Restaurant That Needed More Room
Ruth's Chris has occupied 301 Severn Avenue for three decades, in a building that was once home to Marmaduke's, the sailing bar that closed in the late 1990s. That history matters to Eastport's Alderman Frank Thorp, who called the departure difficult for the neighborhood but said he hopes the building attracts "an even better opportunity in the future."
The move is a straightforward trade of neighborhood character for square footage. Federal Realty Investment Trust bought Annapolis Town Center in October 2025 and has been filling out its dining lineup ever since, with Lovesac, West Elm, and the Greater Annapolis Ballet studio joining the mix. Ruth's Chris will take over the long-vacant space that used to house the Chop House, on the second floor, with its own elevator and a view over the development's entertainment green. Franchisee Steve de Castro described the pull as "an easily accessible area where we know our diners are already spending time."
Here's what's actually changing, side by side:
| Eastport (closing) | Annapolis Town Center (opening) | |
|---|---|---|
| Address | 301 Severn Avenue | 1906 Towne Centre Blvd, Parole |
| Building history | Restaurant row anchor since 1996 | Long-vacant Chop House space |
| Footprint | Not publicly disclosed | 10,150 square feet across two levels |
| Neighbors | Independent restaurants and marine shops | Whole Foods Market, Life Time, Lovesac, West Elm |
| Timing | Closing date not yet announced | Targeted for late fall 2026 |
No closing date has been confirmed for the Severn Avenue location, which means the restaurant will likely keep running dinner service through at least part of the boat show season before the lights go dark. Whatever moves into that corner next won't have a name recognition problem. It'll have a size problem, because 301 Severn Avenue was never built to compete with a Whole Foods-anchored shopping center on square footage. It competed on being the only steakhouse a five-minute walk from the water.
The Shop That Needed the Name
Eastport gained a different kind of tenant this year. MRE Mercantile Men's Clothier opened at 318 Sixth Street on May 30, founded by Travis and Cara Loving. The name is a direct reference to the Maritime Republic of Eastport, the tongue-in-cheek independence the neighborhood has claimed for itself for decades. Travis, a veteran, said "the quirky vibe of the neighborhood and the community spirit inspired us to open here." Cara brought her own influence from Asheville, North Carolina, where she grew up visiting the kind of general store the new shop is modeled after.
The grand opening started at what the founders called the "Crack of Noon," a small joke that only works if you already know Eastport doesn't do early mornings on a Saturday. That's not a detail a chain retailer chooses. It's a detail a shop chooses when its entire pitch depends on the neighborhood recognizing itself in the branding.
MRE Mercantile isn't the only recent signal that outside investment sees value in Eastport specifically. Atlas Restaurant Group, the Baltimore-based operator, acquired a majority stake in Boatyard Bar & Grill earlier this year, one more data point in a broader pattern of ownership change along the waterfront that's worth tracking on its own. But where Atlas bought into an existing Eastport institution, MRE built a new one from scratch, using the neighborhood's identity as its entire premise. Two very different bets on the same six blocks.
The Two Weekends When the Street Isn't Yours
None of this happens in a vacuum. October in Annapolis means the Powerboat Show, running October 8 through 11, followed immediately by the Sailboat Show from October 15 through 18. Both take over City Dock, and both routinely pull tens of thousands of visitors into a downtown that Eastport sits directly across the bridge from.
This year the setup is more complicated than usual, because City Dock itself is mid-construction. As of the second week of September, crews were emptying and relocating the large holding tanks on Upper Dock Street, with the city's construction vendor, Whiting Turner, working to hand the site over to Annapolis Boat Shows in early October so the temporary docks, platforms, and tents can go up on schedule. The show organizers have said the schedule isn't affected by the construction handoff, but the routes in and out of downtown will look different than they have in past years.
The detail that matters most if you live in Eastport: the traffic pattern coming off Compromise Street changes for the duration of both shows. Drivers heading toward the Naval Academy will no longer be able to turn onto Randall Street. Instead, all traffic gets routed up Main Street. If Compromise Street is your normal way out of the neighborhood toward downtown, plan for the detour, not just heavier traffic.
A few other things worth having on your calendar:
- Powerboat Show hours run 10 a.m. to 6:30 p.m. Thursday through Saturday, with a 5 p.m. close on Sunday, October 11.
- Sailboat Show follows the same general pattern the following weekend, October 15 through 18.
- Boat show parking runs through the West Street and downtown garages via the free Magenta Shuttle, or through paid parking at Navy-Marine Corps Memorial Stadium, which runs its own free shuttle to the show.
- Stadium parking shifts to the AACPS lot on Riva Road on October 10 specifically, because of a Navy football game that same day.
If you're used to treating Compromise Street as your quickest route to Main Street or the Academy gates, those two weeks are the time to build in an extra few minutes, not fight the detour.
What This Adds Up To
Put the three threads together and a pattern shows up that none of them reveal on their own. A national chain is trading its Eastport corner for triple the space and mall-anchored parking, because scale is what it needs next. A brand-new local shop chose Eastport specifically because scale was never the point, identity was. And for two weekends this October, the roads that make Eastport a quiet peninsula get temporarily rewired to move tens of thousands of outsiders through it as efficiently as possible.
None of that makes Eastport smaller. It makes clearer what the neighborhood actually trades on, which isn't square footage or parking capacity. It's the fact that a shop can open at noon and name itself after a joke the whole neighborhood already gets, and that's still worth more here than an elevator to a second-floor dining room ever was.
Liz Dooner tracks changes like these across every Annapolis waterfront neighborhood she calls home turf, from a new storefront on Sixth Street to a construction schedule on Dock Street. If you want the next update before it shows up in your feed, reach out to Liz Dooner directly.
