If the 100-foot Christmas tree marks the start of downtown Delray's season, why have vendor tents been going up on the Old School Square lawn every Saturday morning since Oct. 24?
The tree comes on Dec. 1. The campus at 51 N. Swinton Ave. started earlier. The Delray Winter GreenMarket opened on Oct. 24, and from then through Dec. 1 the same campus fills with art fairs, a craft show, a Veterans Day ceremony, an outdoor movie and a full-moon night market. Most of them land on or right beside a market Saturday. By the time the lights go on, the downtown season has been running for more than five weeks.
The Market Set the Start Date
The Delray Beach CRA's season announcement put the 2026–27 opening on Saturday, Oct. 24. The market runs Saturdays from 9 a.m. to 2 p.m. through May 22, 2027. The CRA counts more than 70 local growers, makers and food vendors this season.
That May end date makes the GreenMarket the longest event on the campus, and every other November event is scheduled around it. The art show, the craft fair and the arts district market all fall on market weekends, so a Saturday downtown can easily turn into a full day.
The nearest parking is the Old School Square garage at 95 NE 1st Ave. The City lists it at $1.50 an hour, with free EV chargers.
Each November Saturday Adds Something Around the Market
Here is the GreenMarket's November run, with what else is on each weekend according to the Downtown Delray Beach events calendar.
| Market Saturday | Also on the campus | Also downtown that weekend |
|---|---|---|
| Nov. 7 | Art on the Square Fine Art Show at the Cornell Art Museum, 10 a.m. to 5 p.m., continuing Sunday, Nov. 8, 10 a.m. to 4 p.m. | The Ladies of Simone at Arts Garage, 8 to 10 p.m. |
| Nov. 14 | GreenMarket, 9 a.m. to 2 p.m. | Warehouse Market at Arts Warehouse, 10 a.m. to 3 p.m., and the 6 x 6 Art Extravaganza, Nov. 13 to 14 |
| Nov. 21 | Southern Handcraft Society's 33rd Annual Art & Craft Show, Nov. 19 to 21 | Turkey Trot 5K at Anchor Park, 6:30 to 9 a.m. |
| Nov. 28 | GreenMarket, 9 a.m. to 2 p.m. | First day of the Shop Small Holiday Rewards Pass |
Nov. 21 is the busiest of the four. The Turkey Trot finishes at Anchor Park by 9 a.m., the market opens at 9, and the craft show is already in its third day on the same campus.
The Shop Small pass runs from Nov. 28 through Dec. 31. Purchases at participating downtown businesses earn points, and the points can be redeemed for downtown gift cards. Because it starts on Thanksgiving weekend, holiday shopping downtown gets its own incentive several days before the tree goes up.
Weeknights Fill In Around the Weekends
Old School Square isn't only a Saturday-morning place in November. The weeknight and Friday-evening dates on the downtown and Old School Square calendars cover most of the month:
- Friday, Nov. 6: First Friday Art Walk, 6 to 9 p.m.
- Wednesday, Nov. 11: Veterans Day Ceremony at Old School Square, 9 a.m.
- Thursday, Nov. 12: Open Studio Night at Arts Warehouse, 6 to 8 p.m.
- Friday, Nov. 13: A movie at the Delray Beach Amphitheatre, and the first night of the 6 x 6 Art Extravaganza, 5 to 9 p.m.
- Tuesday, Nov. 24: Full-moon yoga and a night market at the Amphitheatre.
The Cornell Art Museum holds the indoor end of the campus all week. Admission is free. It is open Wednesday through Friday from noon to 6 p.m., Saturday from 10 a.m. to 5 p.m., and Sunday from noon to 5 p.m. Its next exhibition, featuring Helmut Koller, opens with a reception on Thursday, Dec. 3, from 6 to 8 p.m., and runs Dec. 4 through March 21, 2027.
The One Building on the Campus Still Dark
The Crest Theatre is the exception on a campus that is otherwise booked up, which is why this season is happening on the lawn, at the Amphitheatre and in the museum.
The City's project page for the Crest describes a proposed modernization of the auditorium, stage, backstage, dressing rooms, sound and lighting. It gives no reopening date. On Aug. 19, 2025, the City Commission approved a $236,862 design-services agreement for the auditorium renovation. Under that agreement, the designers prepare three concepts, the Commission picks one, and a later design phase follows.
Boca Magazine reported on Feb. 3, 2026 that the Crest still couldn't host performances. The City was running arts classes in the partly reopened building, and three renovation options were on the table.
Smaller improvements to the rest of the campus are funded. The CRA's fiscal 2026–27 work plan sets aside $458,500 for the Old School Square master plan. That includes lighting upgrades and swapping the current roll-up doors for a style that better fits the historic buildings.
Two New Doors on Either Side of Atlantic
The blocks around the campus are adding places to go before or after a Saturday market or a Friday art walk.
North of Atlantic in Pineapple Grove, Preface Wine has opened at 279 NE Second Ave. Boca Magazine described it on Oct. 23 as part wine shop, part wine bar. Founder Jonathan Frutkin's shop turns into a wine bar at 4 p.m., and bottles can be taken home or opened in the store. Labels are scannable for details on each wine. A proprietary system called JJ remembers what you liked and can suggest bottles on your next visit. Preface also plans themed tastings at an Owner's Table and offers tiered memberships with event access and wine education sessions. The GreenMarket packs up at 2 p.m., and Preface's bar opens two hours later.
South of Atlantic, Maman is coming to 40 S. Swinton Ave. on the Sundy Village block. The French-inspired café started in New York's SoHo neighborhood. The Sun Sentinel reported on Oct. 26 that it will open in downtown Delray Beach sometime in November. No exact day has been given. Maman sits on the same street as Old School Square, a short walk south across Atlantic.
Then the Tree Takes Over
On Tuesday, Dec. 1, the campus switches from its fall calendar to its holiday one. The City's tree page lists the Christmas Tree Lighting and Yuletide Street Fair from 6 to 9 p.m. at Old School Square. This is the tree's 33rd year. More than 60 vendors will set up across Atlantic Avenue, Old School Square and Pineapple Grove, with food trucks on Swinton, a silent disco, LED games and a sensory-friendly room. The downtown calendar puts the lighting itself at 7 p.m.
From there, December fills up quickly:
- Dec. 5, 6 p.m.: Holiday School Spectacular at Old School Square.
- Dec. 6, 5 p.m.: Grand Chanukah Festival and Menorah Lighting at Old School Square.
- Dec. 10, 6 to 8 p.m.: Free Cocoa, Cookies and Crafts.
- Dec. 11, 6 p.m.: The Holiday Boat Parade heads south on the Intracoastal from Lantana. Expect the Atlantic Avenue bridge to be held up around 8 p.m.
- Dec. 12, 6 p.m.: The Holiday Parade runs along Atlantic Avenue from the Intracoastal bridge to NW 5th Avenue, with more than 70 floats, bands, dance teams and walking groups. This year's theme is "Neon North Pole."
- Dec. 17, 5 to 9 p.m.: Twilight Tree Market at Old School Square.
The GreenMarket keeps going through all of it, every Saturday from 9 a.m. to 2 p.m., all the way to May 22.
Whether downtown Delray is part of your Saturday routine or you're wondering what it would be like to live a few blocks from Old School Square, Cappy Abraham is happy to talk it through. Our firm has spent decades following how life on South Florida's coast changes with the seasons, and we'd be glad to share what we know about the streets and buildings around the campus. Call us when you're ready.
