This winter, one city block in downtown Delray Beach holds a farmers market every Saturday, four art exhibitions, a fine art show, a free movie night and a 100-foot Christmas tree. Its own stage won't host a single performance.
Old School Square, at 51 N. Swinton Ave., has several landlords. Each piece of the campus is scheduled by a different organization with its own budget cycle. Knowing who runs which piece tells you which dates are firm, which might change, and why the Crest Theatre auditorium has been quiet for so long.
Saturdays belong to the CRA
The GreenMarket is the most predictable thing on the campus. The Delray Beach Community Redevelopment Agency runs it, and its 31st winter season opened October 24. It runs every Saturday from 9 a.m. to 2 p.m. through May 22, 2027. The CRA's roster lists more than 60 food vendors. It also has rotating vendor spaces for small businesses that can't commit to a full or half season, so some booths change from week to week.
The CRA has run this market for three decades, and the dates are published through next spring. That kind of long horizon is unusual on this campus.
After the market, Pineapple Grove has a new stop. Preface Wine, a wine shop and wine bar founded by Jonathan Frutkin, opened at 279 N.E. Second Ave. Boca Magazine reported October 23 that it sells bottles and pours wine in the store, with charcuterie and tastings.
The museum and the lawn run on a one-year contract
The Cornell Art Museum, the grounds and most other campus programming are run by the Delray Beach Downtown Development Authority, under an interlocal agreement with the city. That agreement gets renegotiated every year.
The DDA's management fee is set during the city's regular budget process. The agreement requires the DDA to present its funding request at a commission workshop every May, along with a revenue-sharing plan that sends 10 percent of net revenues from DDA-managed activities back to the city for campus programming. The agreement has been amended in October 2023, October 2024 and March 2026 to update the fee. The latest amendment, Amendment No. 5, covers the 2026–27 fiscal year, and the city's Legistar record lists it as passed on October 13, 2026.
The amendment calls for four payments of $200,000, due by October 15, January 1, April 1 and July 1. They pay for the administration, setup, operation, maintenance and programming of activities, exhibitions and special events on the campus. That adds up to $800,000 for the year. Boca Magazine reported in February that the contract began in late 2022 at roughly $1 million and had dropped to $700,000, after the DDA had asked for $1.6 million in 2024. So this year's figure is a small step back up, still below where the contract started.
On that budget, the DDA has a full winter planned:
- River of Grass and Marleen De Waele–De Bock's Blooming in Color!, at the Cornell through January 24, 2027
- Ron Garrett's Impressions & Expressions, a printmaker retrospective covering more than 40 years, through February 28, 2027
- Icons of Art: The Rockstar Collection, listed with no end date
- Helmut Koller's KOLLERISM: "Vivid & Wild", the next spotlight show, on view December 4, 2026, through March 21, 2027
- Live music at the museum every Wednesday from 3:30 to 5 p.m. Yoga and meditation sessions run on Wednesdays and Fridays.
The lawn is busy too. The Art on the Square Fine Art Show brings about 100 artists to the museum's front lawn and along Swinton Avenue this Saturday and Sunday, November 7 and 8. On Friday, November 13, there's a free screening of The Wizard of Oz at the Amphitheatre. The First Friday Art Walk keeps running at the Cornell. October's edition went from 6 to 9 p.m. with four exhibitions, live portrait sketching and a lantern-pumpkin activity.
Every one of these listings depends on a contract that runs through next September. That's why the exhibition dates stretch into early spring but the campus calendar doesn't go much further.
December is the city's month
For a few weeks, the City of Delray Beach takes over the center of the campus. The 100-foot Christmas tree lighting and Yuletide Street Fair is Tuesday, December 1, from 6 to 9 p.m. It marks 33 years of the tree, with more than 60 vendors along Atlantic Avenue, Old School Square and Pineapple Grove, food trucks on Swinton Avenue, a silent disco, and Santa lighting the tree. According to the DDA's event listing, Atlantic Avenue will close from Swinton Avenue to NE 5th Avenue that night.
Walking through the tree is free. Inside, the Spady Cultural Heritage Museum decorates a "Spady House," there's a "Cornell Museum" display, and St. Paul's Episcopal Church provides the crèche. Holiday Village prices posted by the city:
- Holiday Carousel, $6 per ride, with free rides December 24 and 25
- Ice skating, $6, closed December 24 and 25
- Mini golf, $6, closed December 24 and 25
- Ride All Day wristband, $20
- Santa photo, $10 take-away
Tickets are sold at the Gingerbread Ticket House. On lighting night, the last ticket sells at 8:30 p.m. The city still lists the season schedule for the village and Santa's House as to be determined. The tree night itself is set, but the regular December hours aren't posted yet.
The rest of the city's holiday schedule:
- Dec. 5, 6 p.m.: Holiday School Spectacular
- Dec. 6, 5 p.m.: Grand Chanukah and Menorah Lighting
- Dec. 10, 6 to 8 p.m.: Cocoa, Cookies and Crafts
- Dec. 11, 6 p.m.: Holiday Boat Parade
- Dec. 12, 6 p.m.: Holiday Parade
- Dec. 17, 5 to 9 p.m.: Twilight Tree Market
The Crest, where classes run and the stage doesn't
The Crest Theatre building is busy too, just not on stage. The city's Creative Arts School teaches there, with classes and workshops in ceramics, mixed media and textiles, photography and digital media, culinary arts, drawing and painting, and printmaking. It also offers open studio time, $5 studio days and youth workshops. On October 24 the school held a Halloween event alongside Art in Practice: 2026 Student/Faculty Exhibition.
The auditorium is a different story. The Crest was taken out of the DDA's licensed area in October 2023, so the campus's annual operating contract doesn't cover it. It's now a city capital project. The city's project listing describes modernizing the stage, auditorium, backstage and related systems. Last winter, a consultant gave the commission three options, as Boca Magazine reported. The most basic, at $3.4 million, would do just enough to reopen the theater. A $7.4 million option would allow more varied programming, and an $8.8 million option would allow even more.
That reporting also covered a wider question about who should run the campus long term. The city planned to commission a study of options for Old School Square's future. Mayor Tom Carney has said he wants a different entity to run the whole complex. Commissioner Thomas Markert described the goal as a transition plan. DDA Executive Director Laura Simon spoke about how much the organization had put into the campus, and she agreed on the goal:
"Old School Square needs to be thriving."
That puts the theater in an awkward spot. A multimillion-dollar renovation is a long-term commitment, and the plan for who runs the campus is still being worked out. The annual DDA contract keeps getting renewed, so the galleries and lawn stay programmed. The city's project page lists the theater's scope but no schedule.
Planning a winter around who runs what
Once you know who runs each piece, the calendar is easier to read.
- The GreenMarket is set through May 22, 2027, by the CRA. You can plan Saturdays months ahead.
- Cornell exhibitions have firm closing dates through March 21, 2027, under a DDA contract that runs through the fiscal year. Programming beyond that depends on next May's budget workshop.
- City holiday events have set dates. Holiday Village hours are still being finalized.
- The Crest auditorium has no performance dates. The classrooms keep teaching.
One practical overlap: the DDA's listing says the tree and Santa's Village stay up through New Year's Day, so every GreenMarket Saturday in December shares the campus with them. With the tree up and the market open the same mornings, the block will be busy.
If you own a home within walking distance of Old School Square, the campus calendar is part of what a buyer is paying for, and it's worth telling that story well when you sell. The Silver Team has followed downtown Delray Beach for three decades, and we can show you how the market, the museum and the December events figure into your home's value today. Get your free home valuation and consultation, and we'll walk you through it.