DELRAY BEACH, FL (Boca Post) (Copyright © 2025) — Delray Beach is heading into December with a full calendar of holiday traditions, big crowds, and late-season events stretching across downtown and Old School Square.
The city opens the month with its signature 100-foot Christmas Tree Lighting and Yuletide Street Fair on December 2, running from 6 to 9 p.m. at Old School Square (51 N. Swinton Ave.). The tree marks its 32nd year, anchored by the usual mix of music, food, kids’ crafts, and the steady stream of visitors who pack the square every season. Santa and Mrs. Claus will handle the tree lighting, backed by performances and food trucks parked along Swinton.
Holiday shopping spreads out along Atlantic Avenue and into Pineapple Grove, with more than 60 vendors expected. A silent disco runs through the night, and families can move into Holiday Village for carousel rides, ice skating, mini golf, and other activities. A full schedule is posted at DelrayBeachFL.gov/100ftTree.
The city returns to Atlantic Avenue less than two weeks later for the Delray Beach Holiday Parade, billed this year as the “Festival of Lights.” The parade steps off at 6 p.m. on December 13, moving east to west from the Intracoastal Bridge to NW 5th Avenue. More than 70 floats, marching bands, dance teams, and walking groups are entered.
Judges will select winners in several categories, including Grand Float, Best Non-Profit, Best Dance/Cheer Group, Best Business/Commercial, and Best Marching Band. Through what the city calls a “special connection to the North Pole,” Santa will ride the route aboard a Delray Beach Fire Rescue truck. Additional information is available by contacting event coordinator Danielle Beardsley at [email protected].
Holiday weekend programming continues the next night. The Grand Menorah Lighting and Chanukah Festival begins at 5 p.m. on December 14, also at Old School Square. The event is organized with Chabad of East Delray, featuring live music, traditional Chanukah foods including latkes and donuts, and the community menorah lighting.
Downtown Delray’s broader December lineup includes art walks, live comedy, seasonal markets, and recurring weekend events tied to the holidays:
• First Friday Art Walk – December 5, 6–9 p.m., Downtown Delray Beach
• The Art of Laughter (Rich Aronovitch) – December 5, 8–10 p.m., Arts Garage
• 25th Annual Downtown Delray Beach Art Festival on 4th – December 6–7, 10 a.m.–5 p.m., 401 E Atlantic Ave.
• GreenMarket – December 6, 8, 20, and 27, 9 a.m.–2 p.m., Old School Square Amphitheatre Lawn
• Holiday School Spectacular – December 6, 6–9 p.m., Old School Square Amphitheatre Lawn
• Coco Market – December 7, 9 a.m.–3 p.m., Old School Square Amphitheatre Lawn
• Delray Beach Historical Society Heritage Lecture: Peace River – December 9, 6 p.m., Old School Square Creative Arts School
• Twilight Tree Market – December 11, 5–9 p.m., Old School Square Amphitheatre Lawn
• Sounds of The Set – December 11, 5:30–8:30 p.m., Libby Wesley Plaza
• Holiday Boat Parade – December 12, 6:30–9 p.m., Delray Beach Intracoastal
• Cocoa, Cookies & Crafts – December 18, 6–8 p.m., Old School Square Amphitheatre Lawn
The city expects heavy holiday traffic around Atlantic Avenue, Pineapple Grove, and Swinton throughout the month, with most events drawing families, vendors, and out-of-town visitors.
