The Bay park has always had a north end and a south end. Starting this October, it has a middle. The Plaza opens on Van Wezel Way as the Chalk Festival returns to Burns Square and the Medieval Fair sets its dates in Myakka City, and the effect for anyone who already lives here is that the Saturday map you have been using since 2022 is about to change.
The thesis, before the calendar
Fall 2026 is not a roundup season. It is a re-centering. Three separate anchors — a new civic space at The Bay, a festival returning to the block that invented it, and a fall dining wave clustered inside a fifteen-minute walk — pull the downtown center of gravity south of the Van Wezel and east into Burns Square and Southside Village. Residents who have been treating Main Street as the default answer to "where should we start" are going to want to redraw that line.
The Plaza: what actually opens in October
When the Town Square feature along Van Wezel Way between Municipal Auditorium and the Chidsey Library opens this October, it will carry a familiar name. In April 1964, then-mayor Herschel Mayo dedicated that area as Plaza de Santo Domingo in recognition of Sarasota's sister city in the Dominican Republic, Santo Domingo. In recognition of that dedication, town square will be called, simply, The Plaza.
Two things about that are worth pausing on. First, The Plaza sits at the midpoint of a walkway most residents have not fully absorbed yet. The Cultural District includes a Promenade, opened in 2025, that serves as the front door to The Bay along North Tamiami Trail. The 1,000-foot-long, 16-foot-wide walkway, flanked by 20-foot Royal Palms and canopy trees, connects three of Sarasota's iconic landmarks: the Blue Pagoda, Chidsey Library, and Municipal Auditorium. The Promenade gave residents a north-south spine last year. The Plaza gives that spine a plaza to rest in.
Second, The Plaza's shade structure is designed for programming, not just passing through. The centerpiece of The Plaza is a large shade structure with additional event and gathering spaces for programming, events and rentals. Expect the yoga, Tai Chi, and outdoor movie lineup that currently anchors the first phase to expand into the middle of the park almost immediately.
The restaurant piece is further out. Plans continue to develop for the first of three restaurants, planned to open in fall 2027 at the former site of the U.S. Coast Guard station. Built atop 12-foot pylons for flood resilience, the restaurant will be designed in Sarasota Modern architecture with approximately 5,000 square feet under roof with fewer than 220 indoor seats and 100 outdoor seats. Designed by Sweet Sparkman Architecture, it will be operated by Venice Pier Group, family-owned proprietors who manage Fins at Sharky's and Sharky's on the Pier in Venice and the concessions at Siesta Beach Pavilion. So the Bay in October gives you a new civic room. The bayside dinner is still a year away.
The Chalk Festival returns to where it started
The Chalk Festival is not new. Its home for this fall is.
| Era | Location | Note |
|---|---|---|
| 2007–2013 | Burns Square Historic District, Sarasota | Founded by Denise Kowal |
| 2014–2021 | Venice | Multi-year run on the island |
| 2022–present | Burns Square, downtown Sarasota | Returned to origin |
After six seasons in Burns Square, a historic district in downtown Sarasota, it moved to Venice in 2014, and returned to Sarasota in the fall of 2022. For residents whose mental map of the festival still lives on West Venice Avenue, the practical shift is that the pavement now goes down on S. Orange and S. Pineapple Avenues in Burns Square, a two-block walk from Owen's Fish Camp and a straight shot from The Bay's southern edge.
The 2026 iteration continues the international flower-carpet program folded in during the last cycle. For its 18th iteration, the Festival brought for the first time to the United States multiple delegations of "Infiorata" and "Rangoli" artists together. These artists created carpets using flowers, sand, and other natural materials in an act of devotion. Dubbed "Floralia Infiorata," this exhibition represented an important moment of cultural exchange introducing North American art lovers to these centuries-old artistic traditions. If you last saw the festival in the chalk-only years, plan to spend an extra hour on the floral blocks.
The Medieval Fair now has a real address
For years the Medieval Fair moved. It has stopped moving.
- Dates: Saturdays & Sundays, November 7 – December 6, 2026
- Hours: 9:45 a.m. to 5:30 p.m., rain or shine
- Location: Woods of Mallaranny, 29847 FL-70 E., Myakka City
- Site: 47 acres of native surroundings, giant oak trees, and meadows
- New this year: All tickets are now date-specific and limited; reduced admission during opening weekend (Nov. 7 & 8 only)
The date-specific ticketing is the operational change residents should mark. Once a Saturday sells out, it is closed. For a resident who used to treat the Fair as a "we'll go in November sometime" plan, that is a schedule discipline the event did not previously require.
The fall dining wave, mapped by neighborhood
The new restaurants are not scattered. They cluster.
Downtown / Rosemary
- Warren, a two-story Modern American concept overlooking Selby Five Points Park. This two-story restaurant overlooking Selby Five Points Park promises to be more than just a place to eat. The concept blends Modern American cuisine with an extensive whiskey bar, with premium cuts butchered in-house.
Southside Village
- Mimi, at 1920 Hillview St. Adeline, the acclaimed fine-dining restaurant in Sarasota's Southside Village, closed after telling the Herald-Tribune it endured a "tough summer." The location at 1920 Hillview St. won't sit empty for long. Zaki, who also owns downtown favorite 1592 Wood Fired Kitchen & Cocktails and the newer Lucky 8 in Southside Village, plans to transform the space into Mimi, a more casual and affordable restaurant and cocktail lounge, opening in November.
- Alma de España, Spanish tapas and grill. Alma de España, which translates to Soul of Spain and serves Spanish tapas and grill dishes, has opened in Sarasota's Southside Village at 1830 S. Osprey Ave., Suite 104, in the former space of vegan restaurant Ka Papa Cuisine. Chef/owner Elier Rodriguez is a Cuban native whose resume includes graduating from Le Cordon Bleu College of Culinary Arts Atlanta.
North Trail
- Hob Nob, back at 1701 N. Washington Blvd. A Sarasota original since 1957, the Hob Nob closed in 2024 after 67 years. Now it's back under new ownership with the familiar black-and-white stripes, counter ordering, and a focused menu of smash burgers, chicken tenders, onion rings, fries, and milkshakes.
UTC / Cattlemen corridor
- Mistero 01, star-shaped pizza. The Miami-born pizzeria from chef Renato Viola brings its signature five-point, star-shaped pies to The Market at UTC. Look for the ricotta-filled Star Luca and the Coffee Paolo, plus calzones, a burrata bar, and a Nutella pizza for dessert. Dough is made with imported Italian flour and proofed 72 hours.
- Peachey's Baking Co., second location at 999 Cattlemen Rd, Unit E. Second brick-and-mortar for the beloved Amish-style donut shop. Sourdough-leavened doughnuts, soft pretzels, and coffee drinks in a 1,480 sq ft space.
- Blu Kouzina second location and Kitchen Social, both on Cattlemen. Nashville-born fast-casual chain opens its first Florida location in the former Rusty Bucket space at UTC. Popular St. Armands Circle Greek restaurant expands with a second location at University Town Center.
The Southside pair is the interesting fact. Mimi and Alma de España sit five blocks apart. A resident can eat Spanish small plates at 6, walk to a cocktail lounge at 9, and never touch a car.
A fall Saturday that uses the new geography
Here is one way to spend it. All of these are new or newly relevant this fall.
- 9:00 a.m. Coffee and a sourdough donut at Peachey's on Cattlemen.
- 10:30 a.m. Drive downtown. Enter The Bay from the Promenade at North Tamiami. Walk south past the Blue Pagoda and Chidsey Library. Sit in The Plaza. This is the section that did not exist in September.
- 12:30 p.m. Continue south on foot into Burns Square for the Chalk Festival. Two hours minimum. The flower carpets take longer than you think.
- 3:00 p.m. Owen's Fish Camp on Burns Court, which has been the Chalk Festival's unofficial anchor since 2007.
- 6:30 p.m. Head to Southside Village. Alma de España for tapas or Mimi if you are looking for the softer opening night of a Zaki property.
- The next weekend Reserve a date-specific Medieval Fair ticket in Myakka City before the Saturday you want sells out.
What this actually means for people who already live here
The Bay park's early phases trained residents to think of it as a place to walk the dog at sunset and go home. The Plaza changes that. The 53-acre park isn't even half finished, and the buildout is targeting the end of 2029. Watching a public space fill in mid-life is a rare civic experience, and this October is the section of that experience most residents will remember. Combined with the Chalk Festival's return to its founding block and a Southside dining scene that is, restaurant by restaurant, becoming denser than downtown proper, fall 2026 is the season the neighborhood-scale map of Sarasota gets redrawn.
If your Sarasota life is entering a new chapter this fall, whether that means a larger place near The Bay, a lock-and-leave in Southside Village, or a first look at what the Cultural District's proximity does to downtown values over the next three years, Carla Nix and the Nix Team are ready to walk the map with you.
