Siesta Key Village Didn't Just Come Back. It Picked Up New Habits.
Walk Ocean Boulevard through Siesta Key Village this month and you'll notice two different stories playing out on the same block. The Hub Baja Grill looks exactly like it did before Hurricane Milton tore through its kitchen in October 2024: same margaritas, same tacos, same owners behind the bar. A few doors down at 5204 Ocean Boulevard, Siesta Poke is building bowls of ahi tuna and quinoa in a space that had no restaurant in it before the storms hit. One storefront came back. The other showed up new.
That difference is the actual story of Siesta Key Village heading into fall 2026, and it's more specific than the "the island is back" headline you've probably already read three times this year. The restaurants that reopened after Debby, Helene, and Milton mostly came back as themselves. The businesses that genuinely changed the Village's character are almost all first-time arrivals, and they filled categories the Village simply didn't have before the storms. Poke bowls. Doughnut shops. Turkish doner kebabs. That's not recovery. That's a different mix of businesses than existed in 2023.
The Cottage and The Hub Baja Grill welcomed customers back on November 2, 2024, after 37 days of repair work following Milton's damage to their kitchens and furniture. Both restaurants reopened under the same ownership they had before the storm: Chris Brown and Mike Granthon's Above the Bar Hospitality Group, which also runs Summer House Steak & Seafood and The Beach Club on Siesta Key, along with Smokin' Joe's Pub downtown and Mad Moe's in Osprey. Their return was continuity, not reinvention. If you ate at The Cottage in 2023, the 2026 version is recognizable down to the menu.
That pattern held across most of the Village's headline names. Todd Morton, owner of Morton's Siesta Market, described his store as nearly running on all cylinders again during the recovery, still waiting on customers to fully return. The businesses with the deepest roots on the Key largely came back as the same businesses, just with new drywall and new refrigeration.
The more interesting list is the one made up of places that opened for the first time during the recovery window, because they didn't just refill empty storefronts. They introduced food and retail categories the Village hadn't had.
Siesta Poke is the clearest example. It's Above the Bar Hospitality Group's newest concept, built around a build-your-own bowl format the company's Katie Spelman has described as letting customers construct their own combinations more than a thousand ways. Down the street, Duo Doner & Deli at 5049 Ocean Boulevard brought Turkish-style doner kebabs to the island for the first time, the creation of chef Jakub Skoczylas and his wife Maja Rakowiecka, who came to Siesta Key by way of Sweden, Croatia, and a stint as executive sous chef at Founders Club before opening their own counter-service spot.
The 2025 openings kept building categories the Village hadn't had:
Two long-running favorites also changed hands rather than closing. Kilwins Ice Cream and Made in Rome Gelato both came under new ownership in 2025, keeping familiar names on familiar corners while the operations behind them started over.
Line up the two lists side by side and the pattern is hard to miss.
| What came back | What showed up new |
|---|---|
| The Cottage, same ownership | Siesta Poke, first poke concept on the Key |
| The Hub Baja Grill, same menu | Duo Doner & Deli, first Turkish kebab counter |
| Morton's Siesta Market, same storefront | Parlor Doughnuts, first dedicated doughnut shop |
| Kilwins, same storefront, new owner | Casa Masa, Mexican restaurant |
| Made in Rome Gelato, same storefront, new owner | Rochelle's Boutique, women's fashion |
Reopened businesses restored what the Village had. New businesses expanded what the Village offers. Both things happened at once, which is why "the Village is back" undersells it. It's back, and it's slightly different than it was.
The same split shows up in the Village's event calendar, and it's worth knowing which fall traditions are brand new and which ones have been running since before most current residents moved in.
Safe Treats for Kids is the old one. The Siesta Key Chamber of Commerce has run the Halloween event for close to four decades, and it had to be canceled in 2024 while the island was still recovering from hurricane damage. It returned in 2025 and comes back again this year on October 31 from 3 to 6 p.m., with participating businesses across the island handing out treats to trick-or-treaters.
The Scarecrow Stroll is the new one. The Chamber introduced it for the first time in fall 2025: homemade scarecrows built by local businesses lining the walkways and storefronts of the Village, north and south, from October 1 through 31, with public voting on the Chamber's Facebook page and winners announced November 1. Katie Spelman of Above the Bar Hospitality Group, whose restaurants participated in the inaugural year, said the point was as much about bringing people in as it was about the display itself.
"It's great for the community," Spelman said of the event. "It's great for the island and to get people out walking in the morning, seeing them. They're conversation pieces. It's fun. And then hopefully next year, and in the years that follows, it builds, and it becomes this really cool thing that we can get people from Sarasota, Lakewood Ranch, downtown, all here, even if it's just to take a stroll with this beautiful weather and have an ice cream or have a coffee or just see the sunset and spend time in the village."
That's a Village business owner describing a brand-new event as a deliberate draw for people who don't already live on the Key, which is a different goal than simply restoring foot traffic.
Beyond the two Halloween events, the season's anchor is the Siesta Key Crystal Classic, running Friday, November 13 through Monday, November 16 this year on Siesta Beach. The sand sculpting festival started with its first competition in November 2010 and has grown into an event that now draws roughly 40,000 attendees, according to the Chamber. Twenty-four master sculptors spend the four days turning tons of sand into finished work, with the sculptures lit up for the after-dark display on Saturday evening before the festival wraps on Monday.
The season closes out with the Siesta Key Holiday Parade on November 28, and underneath all of it, the Siesta Key Farmers Market keeps running every Sunday morning in the Village, rain or shine, the way it does year-round.
Put the four fixed points together and the fall calendar reads like this:
If you've been avoiding the Village since the storms because you're picturing boarded windows and construction dust, that picture is two years out of date. But the more useful update isn't just that things reopened. It's that the mix of what's available changed shape while it was rebuilding, and a walk down Ocean Boulevard now turns up options that weren't there in 2023 sitting next to the same handful of places that have anchored the Village for years.
The Village didn't need to become something else to recover. It recovered and became something slightly else anyway, one new storefront and one new tradition at a time.
If you're already living the Siesta Key rhythm and just want another set of eyes on what's changing around you, from new construction to the next wave of openings, that's the kind of local read Arlene Buckmaster tracks block by block across Sarasota's barrier islands. Let's Connect whenever you want the fuller picture.
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