Old School Square's Busiest Fall Saturday Happens Around a Theater That's Still Dark

At 8 a.m. on Saturday, October 24, hundreds of costumed witches on bicycles leave City Hall and pedal toward Old School Square. An hour later the Delray Beach GreenMarket opens its 31st winter season on the same campus. At 10 a.m. the Delray Beach Orchid Society opens its 36th annual sale inside the Vintage Gym. By early afternoon, a costume parade will be heading up from the east end of Atlantic Avenue to finish at the same lawn.

None of it uses the building at the center of the campus. The 323-seat Crest Theatre auditorium is still closed for renovation. Who manages Old School Square long term is also still undecided. October 24 shows the campus doing its job with its lawns, its gym and its amphitheater, run by a patchwork of agencies and nonprofits. Two big decisions about the campus are due at City Hall this fall, and that Saturday is the clearest current picture of what those decisions will shape.

The Day, Hour by Hour

Four organizers have booked the same few acres at 51 N. Swinton Ave. Here is how their schedules overlap.

The listings disagree on one detail. The Downtown Delray Halloween page starts trick-or-treating at 11 a.m., while the City's Kidsfest listing says 11:30 a.m. If you're taking small children, planning on the later start costs you nothing. The City also says the parade lines up at Atlantic Avenue and NE 5th Avenue before heading west to the campus, and that Kidsfest is free.

The tightest window is 11 a.m. to 2 p.m. During those three hours the market, the orchid sale, Kidsfest and trick-or-treating all run at once, and the parade arrives at 1 p.m. If produce is the reason you're coming, the 9 a.m. hour comes after the witches have rolled through and before the strollers arrive.

Opening Day for a Decades-Old Saturday Habit

The CRA's current announcement says it started the GreenMarket in 1996, while a 2021 CRA article gives 1998 as the start year. Either way, the market runs in two seasons, and this Saturday is the start of the longer one. The CRA's season announcement lists more than 70 growers, makers and food vendors. The market runs Saturdays from 9 a.m. to 2 p.m. through May 22, 2027, and accepts SNAP benefits. For SNAP, start at the EBT booth, where you swipe your card for tokens to spend at eligible stalls.

According to the CRA, you'll find locally grown produce, grass-fed beef, fresh-caught seafood, citrus and tropical fruit, eggs, artisan cheese, jams and baked goods. There are also gluten-free, vegan and organic options, cut flowers and plants. Live music runs through the morning. A food area has vendors cooking on site, with seating. On October 24 that seating will be competing with Kidsfest for space.

The CRA hasn't published the 2026 to 2027 vendor list. Past CRA features have spotlighted long-running vendors, among them Gratitude Garden Farm in Loxahatchee Groves, known for mushrooms, sprouts, turmeric and microgreens, and Captain Clay & Son's Fish Market. Opening day is when you'll find out who is back this season.

The Orchid Sale Indoors

The orchid sale is the one event in the Vintage Gym, so it's the place to go when the lawn gets crowded. The Delray Beach Orchid Society's Orchids on the Square offers blooms, orchid supplies and raffles. It opens at 10 a.m. Saturday and runs through 4 p.m. Sunday. Sunday is the quieter option if Saturday's crowd is more than you want.

The Cornell Art Museum is next door. It's open Wednesday through Sunday with free admission, and its current shows include "River of Grass." Of all the buildings on campus, the museum will be the quietest on Saturday.

Parking When Four Events Want the Same Garage

The Old School Square Garage at 95 NE 1st Ave. is the closest structure, and downtown garages charge $1.50 an hour. Older CRA material said the garage was free for GreenMarket shoppers until 4 p.m. The current announcement doesn't mention that, so expect to pay.

The City takes ParkMobile in garages, beach lots and on-street spaces, with a $0.35 transaction fee. Downtown has a 20-minute courtesy period, but the fee still applies. Downtown Delray's parking page notes free parking on some side streets and lots more than a block from Atlantic Avenue. On parade day, a short walk from one of those streets will probably beat circling the garage.

We haven't found a published street-closure notice for October 24. The City posts its weekly traffic advisories on Thursdays, so check on October 22.

The Building Nobody Is Using That Day

The campus is in its current arrangement because of a 2021 decision. In August 2021, the City Commission removed the nonprofit Old School Square Center for the Arts from running the campus after it failed to provide financial audits. Upgrades stopped at that point. In November 2024 the City restarted programming at the Crest itself and handed the rest of the campus to the Downtown Development Authority. The Coastal Star reported that the DDA took it on reluctantly. Classes came back to the Crest's renovated classrooms and are expanding to include ceramics.

The auditorium is a separate project. At its February 3 meeting, the Commission told staff and the design team to move ahead with a staged $7.9 million design that could be built in phases as budget or fundraising allows. Mills + Schnoering Architects estimated the basic rehabilitation at about $3 million. Their top option adds rigging, lighting, in-house audio and video, and livestreaming so the Crest could host touring productions. On May 19, 2026, the Commission approved a $1,273,047 amendment for the architects' design and construction-administration work. That money pays for design work. The construction contract has not been awarded. The architects' proposal laid out several phases, starting in June 2026. Design, construction documents and bidding were projected at about 11.5 months combined, with 14 months of construction administration after that. That timeline is a projection. No reopening date has been announced.

Who Runs the Lawn Next Year Is Still Open

The bigger open question is management of the whole campus. The City has had a whole-campus needs assessment underway with Webb Management, and the architects noted it could affect what the theater needs. At the DDA's August 10 meeting, board members talked about a possible sunset date for the DDA's management of Old School Square. They also raised reduced funding for the program, and one board member suggested another entity might take over. At the same meeting, Assistant City Manager Jeff Oris said the study findings would go to the City Commission on September 22. We haven't found a public record of what was presented or decided.

So the October 24 lineup is a working example of the shared model under review. A CRA market, a DDA events calendar, City-run Kidsfest, an orchid society and a charity bike ride are all sharing one campus. The Webb Management study and the Commission's response will shape who books these lawns and the Vintage Gym in seasons ahead.

What Fills the Campus After October 24

The GreenMarket returns every Saturday through May. Other dates already on the calendar:

• October 30, 5 p.m.: The Delray Beach Historical Society's 12th Annual Fall Fest, co-hosted with Geronimo Tequila Bar and Southwest Grill and the Chamber's Do Good Delray program.
• November 7 and 8: Art on the Square at the Old School Square Amphitheatre, with about 100 artists expected.
• December 1, 6 to 9 p.m.: The City's 100-foot Christmas Tree Lighting and Yuletide Street Fair, with vendors along Atlantic Avenue, Old School Square and Pineapple Grove.

All three are outdoor or along the street, and the Crest auditorium plays no part in any of them.

If you're working out your Saturday mornings around the market this season, or wondering how changes at Old School Square could affect the blocks around it, Tatsiana knows downtown Delray block by block and is glad to talk it through in English or Russian. Contact 1 Ocean Realty for a personalized consultation.