Five Saturdays in a Row on St. Armands Circle, and the Longer Clock Running Underneath

Starting this Saturday, October 17, something is scheduled on St. Armands Circle five Saturdays in a row. An art festival comes first, then a second art show from a different company, then Halloween, then a morning of Ferraris, then a third art festival with a sidewalk sale. Three weeks after that, on Friday, December 4, the Holiday Night of Lights closes out the run.

Those weekends come from five different organizers working on fixed dates. Meanwhile, the buildings, drains and dunes around them are being rebuilt on schedules that run to early 2027, early 2028 and 2031. To read the Circle this fall, you need both calendars.

The Weekend Clock, Date by Date

1. October 17–18: St. Armands Fall Festival of the Arts. Paragon Festivals runs it at 434 St Armands Cir. It goes from 10 a.m. to 5 p.m. both days, admission is free, and Paragon describes it as an outdoor gallery of original work by artists from Florida and other states.
2. October 24–25: St. Armands Circle Fall Art & Craft Show. This one belongs to Blue Ribbon Events. The City of Sarasota's listing puts it at St. Armands Circle Park, 1 St. Armands Cir., from 10 a.m. to 5 p.m. on Saturday and Sunday, with free admission.
3. October 31: Fright Night on St. Armands Circle. The Circle's merchants host it from 5:30 to 8 p.m.
4. November 7: Ferraris on the Circle. It runs from 9 a.m. to 3 p.m., and the St. Armands Circle Association lists Ferrari Drivers SRQ as the sponsor.
5. November 14–15: St Armands Circle Art Festival & Sidewalk Sale. Hours are 10 a.m. to 5 p.m. both days, and the Association lists ArtFestival.com as the sponsor.
6. December 4: the 48th annual Holiday Night of Lights. The Association sponsors this one itself, from 5:30 to 8 p.m.

Each of the three art weekends has its own producer, and that changes what fills the booths. Blue Ribbon describes its shows in general as boutique events with 50 to 150 artisans and a craft focus. Its name for the October 24 weekend says "Art & Craft," while Paragon's October 17 festival is billed as an outdoor gallery of original work. The November weekend adds a sidewalk sale, which brings the Circle's own shops onto the street next to the visiting artists. None of the three organizers has published an artist count for its St. Armands weekend, so you'll learn how big each one is by walking it.

The Holiday Night of Lights is the one date on the list that comes from the Circle itself, sponsored by the merchants' association and now in its 48th year. The Association's listing doesn't say what this year's program includes, so check its events page for details as December 4 gets closer.

Getting On and Off the Circle on Event Days

The Association counts more than 1,600 parking spaces on St. Armands. During events, the City may switch the garage to pay-on-entry so cars can get out faster. No organizer has posted road closures or detours for any of the six dates. The Association's parking and transportation page is the place to check the week of an event.

What the Storefronts Look Like Going Into Season

On event days, the busiest blocks are the ones that changed hands this year. Here's how the Circle has shifted since spring:

• Chocolate Emporium opened a second location at 28 S. Boulevard of the Presidents, starting with a soft opening the week Your Observer reported it on June 30.
• Footgear took over from Cariloha Bamboo by June, according to WWSB. The Association's directory lists it at 349 St. Armands Circle.
• St. Armands Jewelers is moving into the former Jewelry by Cole space at 7 N. Boulevard of the Presidents under new ownership. In June, Your Observer reported that a soft opening was planned "soon." We haven't found a confirmed opening date.
• Speaks Clam Bar at 29 N. Boulevard of Presidents had its last day on March 15. The Lakewood Ranch location is still open, and Your Observer's report didn't name what will go into the St. Armands space.
• Lido Key Tiki Bar at The Ritz-Carlton Members Beach Club held its grand reopening on June 20 and is open to the public, Your Observer reported.

These are the quick changes, a new tenant in an existing space in a matter of months. The slower ones show what the Circle is still rebuilding from.

The Corner on a 2028 Clock

Shore's buildings at 24 and 28 N. Boulevard of the Presidents, on the corner of Madison Drive, have been closed since the back-to-back flooding of the 2024 hurricane season. In July, Your Observer reported that the interiors had been gutted and the building's infrastructure was being fortified. If city approvals go as hoped, the restaurant and boutique could return by early 2028.

The plan reported in May calls for a café and retail on the first floor, a restaurant on the second and hotel units on the third, all depending on city approval. When the project went before the city's Development Review Committee on July 15, staff asked for revisions and clarifications, and the plans have to be resubmitted, per Your Observer. So every art weekend this fall, and probably next fall too, will set up around a corner that is still under construction.

Under the Circle and Along the Beach

The longest clocks belong to projects you won't see from a festival booth. Here's where each one stands as of October 2026:

Your Observer's September report lists the work the flood money could pay for: pump station and backup power upgrades, tide-check valves, underground storage, permeable pavement, bioswales and removable flood barriers. At an October 7 joint meeting of Sarasota and Longboat Key leaders, Sarasota's public works director said the improvements were expected to be done before 2031. The county manages the stormwater system, and the city offered to help if asked, Your Observer reported.

The beach work is moving faster. That same October report said the city had placed about 300,000 cubic yards of sand from New Pass on Lido Key this year. Next comes a vegetated dune running from the Lido Beach Pavilion to the residential properties farther south. The city's project page still lists the dune phase as upcoming, so treat its September dates as the schedule, not as confirmed progress. An April Your Observer report said the dunes would stop short of Ted Sperling Park. The same report said three beach walkovers would be replaced, including the one at the Pavilion, and estimated the dune work at about 75 days. If construction started on September 21 as scheduled, that dune work overlaps with the Circle's fall weekends.

That October report also said work on the John Ringling Causeway was underway and expected to finish later in 2026. The Little Ringling Bridge is still in design, and construction isn't expected anytime soon. For anyone driving to the Circle from downtown, that's one more project to factor into a Saturday trip this fall.

For a closer read of how the Shore approvals or the dune schedule could affect a property on St. Armands or Lido Key, The Thompson Group tracks these projects and can walk you through them. Schedule a private consultation, and we'll go over the timelines that apply to your street.