Delray Beach, FL — Local Events in May & Community Updates
Delray Beach GreenMarket 📆 Saturdays through May 16, 2026 — 🕘 9:00 AM – 2:00 PM 📍 Old School Square, Downtown Delray Beach The Delray Beach GreenMarket wraps up its season in mid-May, giving residents and visitors a final few Saturday mornings to browse 60+ vendors offering fresh produce, baked goods, flowers, artisan foods, and live music. It is a fitting send-off to the season before the market goes on summer hiatus.
First Friday Art Walk 📆 Friday, May 1, 2026 — 🕕 6:00 – 9:00 PM 📍 Pineapple Grove Arts District & Atlantic Avenue The First Friday Art Walk returns May 1, inviting residents to explore galleries, studios, and pop-up exhibits throughout downtown. Live pop-up music, working artist studios, and gallery receptions make this one of the most relaxed and creative ways to spend a spring evening downtown. Eventeny
14th Annual Amazing Delray Beach Challenge 📆 Saturday, May 9, 2026 — 🕗 Check-in 8:30 AM, race starts 9:00 AM 📍 Delray Beach Community Center, 50 NW 1st Avenue A team-based race event open to groups of 2-5 people with divisions for children, adults, and families. Registration runs $25 plus tax for adults and $15 plus tax for ages 17 and under. A fun community-fitness event that draws families, neighbors, and friendly competitors from across the area. The Coastal Star
FREE Twilight Concert: Earth, Wind & Fire Tribute 📆 Friday, May 22, 2026 — 🕔 5:00 – 9:30 PM (music starts at 6:00 PM) 📍 Old School Square, 51 N. Swinton Avenue A free outdoor twilight concert featuring an Earth, Wind & Fire tribute act, kicking off the summer concert series at Old School Square. Bring a chair or blanket and enjoy one of the most popular free entertainment nights in Delray. DowntownDelrayBeach.com
28th Annual Downtown Delray Beach Memorial Day Weekend Craft Festival 📆 Saturday–Sunday, May 23–24, 2026 — 🕙 10:00 AM onward 📍 Downtown Delray Beach A weekend-long outdoor festival featuring paintings, jewelry, glasswork, and pottery, plus a green market with gourmet sauces, handmade soaps, and orchids. A great way to spend Memorial Day weekend strolling Atlantic Avenue. VISIT FLORIDA
Art & Jazz on the Avenue — Beachside Edition 📆 Wednesday, May 27, 2026 — 🕕 6:00 – 9:30 PM 📍 East Atlantic Avenue (Beachside), east of the Intracoastal Bridge Art & Jazz on the Avenue returns to East Atlantic Avenue with live musical performances, mural art, kids' activities, dancing, dining, and locally curated vendors. East Atlantic Avenue from A1A to Seabreeze Avenue will be closed from 2:00 PM to 11:00 PM. One of the signature beachside nights of the year. Boca Raton TribuneBoca Raton Tribune
Sandoway Discovery Center — Marine Life Programs 📆 Daily programs throughout May 📍 Sandoway Discovery Center Sandoway Discovery Center continues daily educational programs on sharks, coral reefs, and local coastal ecosystems. Aquariums, live animal encounters, and feeding demonstrations make it a great rainy-day or beach-day pairing for families.
Live Music & Events at Old School Square 📆 Multiple performances throughout May 📍 Old School Square Pavilion & Campus Old School Square remains a central hub for concerts and cultural events as the spring season transitions into summer. Pair an evening show with dinner along Atlantic Avenue for a full night out.
Community Updates — What's Happening in Delray Beach This May
Beach Renourishment Wrapping Up The large-scale beach renourishment project that began in late January is now in its final stages, with the widened beach taking shape just in time for summer. The project added roughly 1.2 million cubic yards of sand to strengthen storm protection and expand the recreational beach footprint heading into peak season.
Snowbirds Heading Home, Locals Reclaim the Avenue By mid-May, much of the seasonal crowd has packed up and headed back north, and Atlantic Avenue takes on a noticeably more relaxed local rhythm. Restaurants, galleries, and boutiques are still busy on weekends, but parking is easier and reservations are simpler. This is the start of the year-rounder season that locals quietly love.
Real Estate Activity Shifting Toward Next Winter May is when buyers planning ahead for next winter season start touring seriously, while late-season closings from spring contracts are still working through. Northeast buyers, including many from Bergen and Hudson County, often use this window to secure a property before summer prices and competition adjust. Sellers benefit from a more focused buyer pool — the tire-kickers are gone.
Ongoing & Seasonal Highlights
Delray Beach Tennis Center The Tennis Center continues to host clinics, league play, and training. For tennis-focused buyers, proximity to the center remains a real lifestyle advantage — particularly for active adult and resort-style living.
Beach & Outdoor Lifestyle in May May brings warm, beach-ready days with summer humidity just starting to build. Popular local stops include:
Delray Municipal Beach (now widened from the renourishment project) Wakodahatchee Wetlands for birdwatching and boardwalk walks Morikami Museum & Japanese Gardens for tranquil gardens and cultural exhibits Atlantic Avenue shopping and dining district for walkable, urban-style living
Thinking About Moving to Delray Beach This Summer?
Whether you are considering a second home, investment property, or a full relocation from Bergen County to South Florida, partnering with an agent who knows both markets makes a real difference. As a Broker Associate with The Selleck Group at Keller Williams City Views Realty in Fort Lee, NJ, and licensed with Keller Williams Realty Boca Raton in Florida, Scott Selleck helps buyers compare neighborhoods, understand seasonal pricing rhythms, and align lifestyle goals with the right Delray Beach community. 📲 Call or text 201-970-3960
