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Delray's Season Opens on One Saturday, and Old School Square Is Hosting All of It

At 8 a.m. on Saturday, October 24, a few hundred cyclists dressed as witches will start pedaling from City Hall toward Pineapple Grove. An hour later, more than 70 growers, bakers and food vendors will open their stalls on the Old School Square Campus at 51 N. Swinton Avenue. It will be the GreenMarket's first Saturday back since late July. By early afternoon, a costume parade on Atlantic Avenue will be heading toward the same lawn.

Two organizations planned these events separately. Both picked the same Saturday and the same block. If you go downtown that day, it helps to know where their schedules overlap.

Two calendars, one campus

The Delray Beach CRA runs the GreenMarket. The CRA started the market in 1996. October 24 opens its 31st winter season, which runs every Saturday from 9 a.m. to 2 p.m. through May 22, 2027. The 12th Summer GreenMarket ran on the same campus from May 30 until it closed on July 25, 2026. That means opening day ends roughly three months of Saturdays with no market downtown. The City of Delray Beach calendar lists the same date and hours for the winter market's return.

The Halloween program comes from a different set of hosts. The Downtown Delray Beach Halloween page lists four events for the day: the Witches of Delray Ride, Trick-or-Treating on the Avenue, the Halloween Parade and Kidsfest at Old School Square. Each one either ends at the campus or takes place on it.

Laid out hour by hour, the schedules look like this:

Time What is happening Where
8 a.m. to 11 a.m. 15th Annual Witches of Delray Ride City Hall to Old School Square
9 a.m. to 2 p.m. Winter GreenMarket opening day Old School Square Campus
11 a.m. to 1 p.m. Trick-or-Treating on the Avenue Atlantic Avenue
11 a.m. to 3 p.m. Kidsfest Old School Square
1 p.m. Halloween Parade Atlantic Avenue and NE 5th Avenue to Old School Square

From 9 a.m. to 11 a.m., the ride and the market share the morning. The ride ends at the campus while the market is getting going. From 11 a.m. to 2 p.m., trick-or-treating, Kidsfest and the parade overlap with the market's second half. Kidsfest keeps going for one more hour after the vendors pack up.

The morning window, and why it is short

The market's quiet stretch is shorter than usual. The ride starts at 8, but it is a moving event. The announcement describes a roughly two-mile route from City Hall down Atlantic Avenue into Pineapple Grove, with about 300 riders expected. The Downtown Delray page has the ride ending at Old School Square by 11 a.m. The turnout estimate has a track record. WFLX reported that 300 witches rode in the 14th annual ride last October.

That leaves about two hours, 9 a.m. to 11 a.m., when the campus is mostly a farmers market with a costumed bike ride arriving. For a produce run, this is the clearest part of the day. The CRA's lineup includes locally grown produce, grass-fed beef, fresh-caught seafood, just-picked citrus and tropical fruit, farm-fresh eggs, artisan cheese, jams, baked goods, cut flowers and plants. Live music plays through the morning. There is also a food area where vendors cook on site, with seating. The market accepts SNAP benefits through an EBT booth, where shoppers swipe a card for tokens before they shop.

The CRA's announcement places the market on the Old School Square Campus and describes its vendor categories, but it doesn't name individual vendors or say where on the campus the stalls will go. Kidsfest is described as a day of games and bounce houses. Exactly how the two events split the lawn will only be clear on the day.

Eleven to two, when everything overlaps

At 11 a.m., the day shifts from a market morning to a family festival. Trick-or-treating with participating merchants moves onto Atlantic Avenue, and The Boca Raton Tribune reported in September that the Avenue will be closed to traffic for it. The two event pages list different start times. Downtown Delray says 11 a.m. to 1 p.m., and Old School Square says 11:30 a.m. to 1 p.m. If you are driving through, plan on the earlier time.

The parade lines up at 1 p.m. at Atlantic Avenue and NE 5th Avenue. Anyone in costume can join, and it moves west along Atlantic to Old School Square. When marchers reach Kidsfest, the Rotary Club of Delray Beach hands out free ice cream. The sources don't agree on which year of the parade this is, but every listing gives the same route.

For a GreenMarket regular, the parade timing matters. At 1 p.m., marchers start heading toward the campus while vendors are in their last hour. If you arrive after noon, expect a market with a parade heading its way.

The CRA's season notice adds one more consideration. It says market closures caused by citywide events will be posted on the GreenMarket webpage and social media. Both the CRA and the city list October 24 as opening day, so no closure is expected. If you are planning your Saturday around the market, check the @delraygreenmarket account that morning.

Getting there with Atlantic closed

No special event shuttle or extended trolley service has been announced for the day. The regular options still apply:

  1. Old School Square Garage, 95 NE 1st Avenue, is the closest garage to the campus. Downtown Delray lists the garage rate at $1.50 an hour.
  2. Side streets and lots more than a block from Atlantic Avenue have free parking, according to the same page. On a day when the Avenue is closed, these spots may be easier to leave from than the central blocks.
  3. Freebee, the city's free on-demand ride service, covers much of downtown east of I-95 to A1A, between Gulfstream Boulevard and SW 10th Street. Its posted Thursday through Saturday hours start at 11 a.m., so it is not running during the early market hours.
  4. The city's traffic advisories are posted on City Hall's social media every Thursday. October 22 is the Thursday before the event, and any street-by-street closure details would most likely appear then.

If you plan to ride

Registration for the Witches of Delray Ride is still open on the Achievement Centers for Children & Families registration page. A ticket is $100, riders must be at least 16, and everyone signs a waiver. Early registration was $75 and ended October 1. Proceeds go to the Achievement Centers for Children & Families. Its event page says its programs serve more than 700 local children and their families. Because the ride ends at Old School Square, riders arrive at the campus during the market's first two hours.

What opening day starts

October 24 also starts a run of Saturdays and holiday events on the same campus. The GreenMarket will be there every Saturday through May 22, 2027. Two weekends later, Art on the Square brings about 100 juried artists to the Old School Square Amphitheatre on November 7 and 8. On Tuesday, December 1, the 100-foot Christmas Tree Lighting & Yuletide Festival runs from 6 to 9 p.m. at Old School Square, with the lighting at 7 p.m. The tree and Santa's Village stay up through New Year's Day.

The restaurants near the campus are changing over the same weeks. Park Tavern at 32 SE 2nd Avenue serves for the last time on Sunday, October 18, after 15 years downtown, as reported by The Palm Beach Post. That is six days before the market reopens. North of Atlantic, Ethereal had opened as a fine-dining restaurant at 324 NE 3rd Avenue by mid-September, according to Boca Magazine. The Downtown Development Authority has also extended Restaurant Month deals at 15 downtown restaurants through October 31, The Palm Beach Post reported, including select prix-fixe menus and happy-hour specials. If you stay downtown after the market closes at 2 p.m. on October 24, those deals still have a week left.

At The Olive Belcher Team, we follow downtown Delray's calendar one Saturday at a time. If you would like to talk about life near Old School Square this season, or about what a home a short walk from the GreenMarket offers, we invite you to Request a Private Consultation.

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