Old School Square

Name: Delray Winter GreenMarket
Start: 2026-12-05T09:00:00-05:00
End: 2026-12-05T14:00:00-05:00
Location: Old School Square

51 N Swinton Ave
Delray Beach, FL 33444 United States Get Directions

561-243-1077

https://delrayoldschoolsquare.com/events

Outdoor concerts, art displays, yoga, drum circle, and more.

Old School Square – Downtown Delray Beach’s Cultural Arts Campus

Located in the heart of downtown, Old School Square is a historic 6-acre cultural campus dedicated to bringing the community together through diverse, high-quality, and interactive arts experiences—all while honoring its century-old heritage.

Once early 20th-century school buildings, the beautifully restored campus now serves as a vibrant hub for arts, culture, and events:

Cornell Art Museum – Contemporary fine arts museum showcasing rotating exhibitions.
The Vintage Gym – A unique venue for weddings and private events.
Crest Theatre Building – Home to a performance theatre and creative arts school.
Outdoor Amphitheatre – Hosting live music, concerts, and community gatherings.
Public Park & Parking Garage – Providing welcoming green space and on-site convenience.

Spanning an entire city block at Atlantic Avenue and Swinton Avenue, Old School Square is among Delray Beach’s premier cultural destinations, hosting everything from fine art exhibits and theatrical performances to large-scale concerts and private celebrations.

📍 Address: 51 N. Swinton Avenue, Delray Beach, FL 33444
📧 Inquiries & Rentals: oss@downtowndelraybeach.com
📞 Phone: (561) 243-1077

Categories: Delray Beach

Events at this venue

October 2026
The Witches of Delray 15th Annual Witches Ride

Featured October 24 @ 8:00 am - 11:00 pm

Old School Square 51 N Swinton Ave, Delray Beach, FL, United States

Still a little short of Yoast’s 30% mark. This version adds more transition words and turns a few short lines into full sentences. Body copy The 15th Annual Witches of Delray Bike Ride returns Saturday, October 24, 2026, for one of Downtown Delray Beach’s most spirited Halloween traditions. Hundreds of witches will put on their […]

Free
Delray Winter GreenMarket

Featured October 24 @ 9:00 am - 2:00 pm Delray Winter GreenMarket

Old School Square 51 N Swinton Ave, Delray Beach, FL, United States

Delray GreenMarket Returns to Old School Square Join the Delray CRA for Downtown Delray’s most popular event—the Delray GreenMarket. The winter season kicks off Saturday, October 24, 2026, and runs through May 22, 2027. Every Saturday morning, the open-air farmers market takes over Old School Square and transforms into a lively community destination. Established in […]

Free
Halloween Kidsfest at Old School Square

October 24 @ 11:00 am - 3:00 pm

Old School Square 51 N Swinton Ave, Delray Beach, FL, United States

Trick-or-Treating on the Avenue Time: 11:30 am—1:00 pm Location: Downtown Delray Beach Trick-or-Treat Your Way Down the Avenue. Brought to you by the Downtown Development Authority. More info (561) 243-1077 64th Annual Halloween Parade Time: 1:00 pm Location: SE/NE 5th Ave to Old School Square You’re not just watching the parade—you’re in it! Grab your […]

Free
Delray Winter GreenMarket

Featured October 31 @ 9:00 am - 2:00 pm Delray Winter GreenMarket

Old School Square 51 N Swinton Ave, Delray Beach, FL, United States

Delray GreenMarket Returns to Old School Square Join the Delray CRA for Downtown Delray’s most popular event—the Delray GreenMarket. The winter season kicks off Saturday, October 24, 2026, and runs through May 22, 2027. Every Saturday morning, the open-air farmers market takes over Old School Square and transforms into a lively community destination. Established in […]

Free
November 2026
Coco Market Wellness Festival

November 1 @ 9:00 am - 3:00 pm Coco Market Wellness Festival

Old School Square 51 N Swinton Ave, Delray Beach, FL, United States

Coco Market Returns Sunday, June 7th! Coco Market is a vibrant monthly wellness market that brings the community together to connect, heal, and celebrate wellness. Held on the first Sunday of every month (with a few exceptions) at Old School Square in Downtown Delray Beach, the market supports local businesses while creating a welcoming space […]

Free
Delray Winter GreenMarket

Featured November 7 @ 9:00 am - 2:00 pm Delray Winter GreenMarket

Old School Square 51 N Swinton Ave, Delray Beach, FL, United States

Delray GreenMarket Returns to Old School Square Join the Delray CRA for Downtown Delray’s most popular event—the Delray GreenMarket. The winter season kicks off Saturday, October 24, 2026, and runs through May 22, 2027. Every Saturday morning, the open-air farmers market takes over Old School Square and transforms into a lively community destination. Established in […]

Free
Delray Winter GreenMarket

Featured November 14 @ 9:00 am - 2:00 pm Delray Winter GreenMarket

Old School Square 51 N Swinton Ave, Delray Beach, FL, United States

Delray GreenMarket Returns to Old School Square Join the Delray CRA for Downtown Delray’s most popular event—the Delray GreenMarket. The winter season kicks off Saturday, October 24, 2026, and runs through May 22, 2027. Every Saturday morning, the open-air farmers market takes over Old School Square and transforms into a lively community destination. Established in […]

Free
Delray Is Going To The Dogs

November 15 @ 12:00 pm - 4:00 pm

Old School Square 51 N Swinton Ave, Delray Beach, FL, United States

Date and Time Sunday, Nov 15, 2026 12PM - 4PM Location Old School Square 51 N Swinton Ave Details Delray is going to the dogs invites you to their 7th Annual Pooches & Presents in the Park! Bring your family, friends, and your dog and enjoy a festive day that supports pets in need! THIS […]

Free
Delray Winter GreenMarket

Featured November 21 @ 9:00 am - 2:00 pm Delray Winter GreenMarket

Old School Square 51 N Swinton Ave, Delray Beach, FL, United States

Delray GreenMarket Returns to Old School Square Join the Delray CRA for Downtown Delray’s most popular event—the Delray GreenMarket. The winter season kicks off Saturday, October 24, 2026, and runs through May 22, 2027. Every Saturday morning, the open-air farmers market takes over Old School Square and transforms into a lively community destination. Established in […]

Free
Delray Winter GreenMarket

Featured November 28 @ 9:00 am - 2:00 pm Delray Winter GreenMarket

Old School Square 51 N Swinton Ave, Delray Beach, FL, United States

Delray GreenMarket Returns to Old School Square Join the Delray CRA for Downtown Delray’s most popular event—the Delray GreenMarket. The winter season kicks off Saturday, October 24, 2026, and runs through May 22, 2027. Every Saturday morning, the open-air farmers market takes over Old School Square and transforms into a lively community destination. Established in […]

Free
December 2026
Holiday Magic 100 Foot Christmas Tree Lighting Delray Beach

December 1 @ 6:00 pm - 9:00 pm

Old School Square 51 N Swinton Ave, Delray Beach, FL, United States

Kick off the holidays with one of Delray Beach’s most beloved traditions — the lighting of our iconic 100-foot Christmas Tree. Join family and friends as Santa flips the switch at 7 PM, transforming the magnificent tree into a dazzling display of lights and holiday cheer. Once the tree is glowing, step inside to experience […]

Free
Delray Winter GreenMarket

Featured December 5 @ 9:00 am - 2:00 pm Delray Winter GreenMarket

Old School Square 51 N Swinton Ave, Delray Beach, FL, United States

Delray GreenMarket Returns to Old School Square Join the Delray CRA for Downtown Delray’s most popular event—the Delray GreenMarket. The winter season kicks off Saturday, October 24, 2026, and runs through May 22, 2027. Every Saturday morning, the open-air farmers market takes over Old School Square and transforms into a lively community destination. Established in […]

Free