This Friday, September 4, Fleming Street does the thing it does on the first Friday of every month. Doors prop open between the 500 block and Grinnell Street, string lights come on before the sky finishes going pink, and for three hours a stretch of Old Town that spends most evenings as a quiet walk-through between Duval and the harbor turns into something closer to a block party. If you've lived here more than a season, you already know the shape of it. What you might not know is that the version running this month is not the same event that runs in January.
Two things are true on Fleming Street in 2026 at the same time. A hundred-year-old grocery store on the 500 block just hit its centennial, run by the same family that has kept it open through a fire, a rebuild, and six decades of a changing island. And a few doors down, a coffee roaster with 35 years of history at Mile Marker 15 is trying to plant a flag back downtown for the first time. One of those stories moves on a scale of generations. The other is happening in real time, and it isn't finished yet.
What the calendar promises
First Fridays on Fleming started as a shop-local initiative among boutique owners on what locals call the Fab 500 Block, and it has held its shape for years: 6 to 9 p.m., the first Friday of the month, running from the 500 block down toward Grinnell. The event calendars describe a familiar lineup of categories, boutiques, galleries, antique shops, artist studios, a bookstore, a yoga studio, restaurants and a cocktail lounge, all opening their doors at once for exhibition openings, jewelry trunk shows, book signings and live music.
Read enough of the visitor-facing copy and you'd assume every storefront on the block participates every month with equal enthusiasm. That has never quite been the case, and it matters more right now than it does in the high season.
The season nobody prints on the flyer
Buried in the event listings, easy to miss if you're only skimming the highlights, is a line that tells you more about how this street actually functions than anything else in the copy: not every business joins in during the summer and fall months. That's not a rumor. It's printed by the organizers themselves.
Late August into September is exactly that window. So the First Friday you're walking into this week is a legitimate version of the event, just a thinner one than the version you'll get in November through May, when the full roster of galleries, boutiques and pop-ups tends to come back online. If you're new to the block and expecting the crowded, everything-open night you saw in photos from last winter, this Friday will look a little sleepier. That's not a sign the event is fading. It's a sign you're seeing it in its off-season register, the same way a restaurant runs a shorter menu in a slow month without closing.
If you only have one Friday evening to give it this fall, treat it as a preview rather than the main event, and circle back once the cooler months bring the full lineup out again.
The building that hasn't blinked in a hundred years
While the monthly event ebbs and flows with the season, one anchor on that same block hasn't changed in any way that matters since the Truman administration. Fausto's Food Palace, at 522 Fleming Street, turns 100 this year. Fausto Castillo, a Cuban-born cigar maker, opened the original grocery in 1926 with his wife, Ana Luisa Alvarez. Management passed to their daughter and her husband, Carl Weekley, in 1946, and the store moved to its current Fleming Street address in 1949.
It hasn't always been an easy hundred years. A fire destroyed the building in August 1966, and the family rebuilt and reopened it in 1967, setting the new structure back from the street to make room for the parking lot that's still there along Bahama Street today. Third-generation brothers Jimmy and Alton Weekley now run the business, Jimmy at the Fleming Street store and Alton at the second location on White Street. That second location matters if you've read our field guide to the Third Thursday Walk on White in The Meadows: that art stroll literally starts at Fausto's and runs down White Street, which means the same family grocery anchors two of Old Town and The Meadows' recurring neighborhood rituals from opposite ends of town.
That kind of continuity is rare on an island where storefronts turn over with the tourist seasons. It's also the quiet backdrop against which this year's more uncertain story is playing out a few doors away.
Here's how the two timelines on this stretch of Fleming actually line up:
| Year | What happened |
|---|---|
| 1926 | Fausto Castillo opens a small grocery store in Key West |
| 1949 | Fausto's moves to its current address at 522 Fleming Street |
| 1966 | A fire destroys the Fleming Street store |
| 1967 | Fausto's reopens on the same site |
| 1991 | Baby's Coffee is founded at Mile Marker 15 by Gary and Olga Teplistky |
| 2024 | Joe and Carnella Bracciale purchase Baby's Coffee and announce plans to return to downtown Key West |
| 2026 | Fausto's marks its 100th anniversary; Baby's Coffee targets a new storefront at 518 Fleming Street |
The newcomer testing that same block
Baby's Coffee has meant one address to most people on this island for more than three decades: the roastery out at Mile Marker 15 on Overseas Highway, known for its own-roasted Arabica beans and blends like the Key West Old Town Roast and Baby's Cuban Roast. When Joe and Carnella Bracciale bought the company in 2024, they said they wanted to bring the brand back to Old Town, where it started. This year that plan became specific: a permit application filed with the Florida Department of Business and Professional Regulation for a storefront at 518 Fleming Street, a few doors from Fausto's, with co-owner Carnella Bracciale telling local press the shop should be serving Old Town locals and visitors by July, in time for Hemingway Days.
Hemingway Days ran July 22 through 26 this year, its 45th edition, centered as always around Sloppy Joe's Bar on Duval Street. That target date has come and gone. As of this writing, Baby's Coffee's own website and its most recently updated directory listings still show only the original Mile Marker 15 address as an active location, with no separate downtown storefront listed yet. That doesn't mean the plan fell through. It's common for a small shop's digital footprint to lag its actual opening by weeks, especially mid-summer in a town where permitting and construction timelines have a way of stretching. If you're on Fleming Street and see the doors open at 518, that's your confirmation, not a press release.
What continuity actually looks like here
Put those two stories next to each other and you get a more accurate read on this block than either one gives you alone. Fausto's hundredth year is proof that Old Town can hold a business in place through a fire, a rebuild, and a full century of the island changing around it. Baby's Coffee's slow, still-unconfirmed arrival is proof that even a well-known, well-funded brand with three decades of loyalty behind it can't just walk onto Fleming Street and expect an easy landing. The street rewards patience and generational commitment more than it rewards a good plan and a permit filing.
That's worth knowing if you're the kind of person who pays attention to which storefronts stick and which ones cycle through on Old Town's tighter blocks. The block looks stable from a distance. Up close, it's holding two very different kinds of time at once.
If you're planning your Friday
- Go between 6 and 9 p.m. on the first Friday of the month, starting on the 500 block and working down toward Grinnell Street.
- Expect a lighter lineup through September than you'll see once the full winter season resumes in November.
- Stop into Fausto's on Fleming even if you're not shopping. A hundred years on the same block is worth a look inside.
- Check for open doors at 518 Fleming before assuming Baby's Coffee has landed. The storefront, not the calendar, is the confirmation.
Old Town rewards the kind of attention that notices which businesses have been here since before you moved in and which ones are still finding their footing. If you're weighing what a home on this stretch of the island is actually worth, that same attention to detail is what SoldByStacy brings to every conversation. Reach out any time for a complimentary home valuation, no obligation, just a straight read on where your Old Town property stands today.
