Friday around 7, the block between 25th and 27th Avenue in downtown Gulfport now works the way city blocks are supposed to work. Park once. Eat at one address, have a drink at another, cut through an alley painted floor to ceiling with murals, end up somewhere else entirely, and never move the car. That loop did not exist this time last year. What is strange, if you slow down and look at the addresses, is that almost none of the buildings making it possible are new. They are old buildings that have been sitting there for decades, finally doing something again.
That is the actual story of downtown Gulfport's current run of openings. It is not a construction boom. It is a reoccupation boom, and the distinction matters if you live here, because it changes what "new" even means on your side of town this year.
The Pharmacy Becomes A Diner
The clearest example sits inside the old Triplett-Day Pharmacy building, which held a pharmacy for 65 years before chef Robert St. John opened The Downtowner there on June 9, 2026. It is St. John's 27th restaurant and his first on the Gulf Coast, built around what he calls heritage cuisine, the kind of cooking he says came from his grandmother's kitchen. He described the menu simply: "It's just real food for real people."
What makes the opening a downtown story rather than just a restaurant story is the building itself. A pharmacy that served Gulfport for 65 years does not get demolished and replaced. It gets a new tenant who keeps the shell, the bones, the reason the corner mattered in the first place, and adds a breakfast bar and a lunch crowd on top of it. If you have walked past that building for years without giving it much thought, that is the point. It was never empty in the way a vacant lot is empty. It was just waiting.
Two Old Buildings Learned To Pour Cocktails
A few blocks over, the same pattern shows up twice more, and both times it is a hotel doing the reoccupying.
Hotel Vela sits on the corner of 24th Avenue and 14th Street in one of downtown's most historic buildings, 16 rooms built around exposed brick and original floorboards rather than around new drywall. Its restaurant, Siren Social Club, is a speakeasy-style room serving refined European food and cocktails, run by chef Austin Sumrall and his wife Tresse. It is the kind of place where the appeal is not that it is shiny and new but that it clearly is not, that the brick over the bar has been there since before the hotel had a name.
Not far away, The Markham Hotel opened its own answer with The Library Restaurant & Bar, a room built for breakfast, weekend brunch, dinner, and a nightly bar and tapas menu, anchored by a striking central bar in a building that has been part of downtown's skyline for years.
Here is a way to see how much this changes the map without inventing anything:
| Building | What It Was | What It Is Now |
|---|---|---|
| Triplett-Day Pharmacy | Pharmacy, 65 years | The Downtowner |
| Historic building, 24th Ave & 14th St | Vacant or underused downtown structure | Hotel Vela and Siren Social Club |
| The Markham building | Downtown hotel property | The Library Restaurant & Bar |
None of these required a permit for new construction on an empty lot. Each one required someone deciding an old building downtown was worth finishing rather than walking past.
The Alley That Makes It All Walkable
The thing tying these blocks together, literally, is Fishbone Alley, and its own history follows the same logic as the buildings around it. It started as a plain utility alley used for trash and maintenance. After Hurricane Katrina tore through downtown in 2005, crews doing repair work uncovered brick pavers from the early 1900s buried under the asphalt, a physical layer of Gulfport that had been there the whole time, just covered up. In 2016, Gulfport Main Street built a public art and economic development project on top of that discovery rather than paving over it again, and the alley that resulted, tucked between 26th and 27th Avenues, has been filling in with murals ever since, including a 60-foot octopus painted by local artist Ryan D. Merrill.
A recent piece in Magnolia Tribune put the point simply: Gulfport chose to build something new around something old rather than erase it. That is exactly what has happened to the alley and to the restaurants and hotels around it. The bricks under your feet in Fishbone Alley are the same ones under the streets a century ago. The buildings on either side of the alley are the same ones that have stood there for decades. What changed is that they are all occupied and open at the same time now, which is the reason a Friday night downtown finally connects instead of requiring four separate drives.
The Other Kind Of New, Out By The Harbor
Not everything happening around Gulfport this year fits the reoccupation pattern, and the contrast is useful. Out toward the water, the growth looks different. Bacchus on the Bluff opened in March 2026 with waterfront views and a menu built around seafood, steaks, and handcrafted cocktails, part of a small portfolio run by brothers Jourdan and Field Nicaud, who also operate Bacchus locations in Pass Christian and Ocean Springs. Near Centennial Plaza Resort, Hippie Fish combines dining with arcade games and a designed mini golf course, a family-facing concept built for a resort crowd rather than a downtown one.
These are legitimately new builds and new concepts, aimed at a different kind of evening than the one downtown offers. Downtown's new wave is about walking between old buildings that finally have tenants again. The harbor's new wave is about building fresh entertainment on ground that did not have a restaurant or arcade on it before. Both are real growth. They are just not the same growth, and conflating them misses what is actually interesting about this year, which is that downtown's revival cost almost nothing in new concrete.
What This Adds Up To If You Already Live Here
If you have lived in Gulfport for a while, you have probably driven past the old pharmacy building, the corner at 24th and 14th, and the alley a hundred times without much reason to stop. What changed is not the geography. It is that all three now have a reason to visit on the same night, and none of them required the city to widen a road, add a parking deck, or clear a lot.
A weeknight now looks like this without much planning: dinner at The Downtowner in a building that has fed Gulfport in one form or another for 65 years, a cocktail at Siren Social Club a few blocks down, a walk through Fishbone Alley under the octopus mural and whatever new piece has gone up since your last visit, and a last stop at The Library if the night calls for one more round. None of it requires driving to the beach road or out toward the casinos for a destination meal. The destination moved into buildings that were already here.
That is worth knowing even if you have no plans to buy or sell anything. It says something about how a downtown grows back after decades of being overlooked, not by tearing itself down and starting over, but by someone finally deciding the old shell was worth finishing.
Rain keeps a close eye on how downtown Gulfport and the rest of the Coast are actually changing, block by block, because that is the same texture we bring to how we market and manage property here. If you are curious what a specific corner or building downtown is worth, or how a neighborhood like this one holds its value over time, Talk With an Advisor and we will walk through it with you.
