Delray Beach, FL: October Events, Halloween Happenings and Community Updates
October is when Delray Beach turns the corner into season. The Winter GreenMarket returns, the galleries open their fall shows, and on Saturday, October 24, the whole downtown turns into Halloween. It is also the month when Northeast buyers start writing offers to be settled by January. This is what is happening this month, plus the local updates that matter if you are watching this market from the Northeast.
Halloween in Downtown Delray: Saturday, October 24, 2026
This is the biggest day of the month, and one of the most fun days of the year to be downtown.
15th Annual Witches of Delray Ride
Time: 7:00 AM to 11:00 AM
Route: Starts at City Hall and ends at Old School Square
Hundreds of costumed witches ride bikes through downtown, benefiting the Achievement Centers for Children and Families. Registration is open online for riders. Spectators line the route early.
Trick-or-Treating on the Avenue
Time: 11:00 AM to 1:00 PM
Location: Atlantic Avenue
Participating merchants hand out candy along the Avenue.
Kidsfest
Time: 11:00 AM to 3:00 PM
Location: Old School Square
Food, vendors, arts and crafts, and entertainment.
Halloween Parade
Time: 1:00 PM
Route: Federal Highway to Old School Square
Everyone in costume forms the parade.
Lil Flockers Halloween Brunch and Parade
Time: 11:00 AM to 2:00 PM
Location: THROW Social Delray Beach
Delray Winter GreenMarket Opening Day
Time: 9:00 AM to 2:00 PM
Location: Old School Square
The GreenMarket returns for the winter season the same morning.
Orchids on the Square
Dates: Saturday, October 24 and Sunday, October 25
Time: 10:00 AM to 5:00 PM
Location: Vintage Gym at Old School Square
Plan on a busy downtown. Arrive early, and expect crowds and limited parking from the morning ride through the afternoon parade.
More Halloween and Fall Events
Sip and Shop: Pawloween
Date: Saturday, October 17
Time: 4:00 PM to 7:00 PM
Location: The Standard
An evening shopping market with a pet-friendly Halloween theme.
YPAD Masquerade Ball
Date: Friday, October 23
Time: 8:00 PM to 11:00 PM
Location: Aloft Delray Beach
12th Annual Fall Fest
Date: Friday, October 30
Time: Starts at 5:00 PM
Location: Delray Beach Historical Society
SoFlo's Biggest Halloween Costume Party
Dates: Saturday, October 31 into Sunday, November 1
Time: 5:00 PM to 2:00 AM
Location: THROW Social Delray Beach
Local Events in October 2026
Cornell Art Museum: Two Fall Openings
Date: Thursday, October 1
Time: 6:00 PM to 8:00 PM
Location: Cornell Art Museum at Old School Square
"River of Grass" and the Marleen De Waele-De Bock spotlight exhibition "Blooming in Color" open the same evening.
First Friday Art Walk
Date: Friday, October 2
Time: 6:00 PM to 9:00 PM
Location: Downtown Delray Beach
Galleries, studios and pop-up exhibits open across downtown. Free to attend. The Creative Arts School at Old School Square holds its "Art in Practice" opening reception the same night, 6:00 PM to 9:00 PM.
The Blues Brothers Soul Band
Date: Friday, October 2
Time: 8:00 PM to 10:00 PM
Location: Arts Garage, 94 N.E. Second Avenue
Arts Garage shows sell out, so book ahead.
Read It Write It Delray Beach
Date: Saturday, October 3
Time: 11:00 AM to 3:00 PM
Location: Delray Beach Public Library
Coco Market Wellness Festival
Date: Sunday, October 4
Time: 9:00 AM to 3:00 PM
Location: Delray Beach Amphitheatre at Old School Square
Free outdoor wellness market with vendors, movement classes and local makers.
National Night Out
Date: Wednesday, October 7
Time: 5:30 PM to 8:30 PM
Location: Old School Square
The Delray Beach Police Department's community evening. A good way to meet the neighborhood.
Novecento 35th Anniversary
Date: Friday, October 9
Time: 4:00 PM to 11:00 PM
Location: Novecento
FLOCK-toberfest
Date: Saturday, October 10
Time: 4:00 PM to 2:00 AM
Location: THROW Social Delray Beach
Ron Garrett Retrospective Opening
Date: Sunday, October 11
Time: 3:00 PM to 5:00 PM
Location: Cornell Art Museum at Old School Square
Nicole Henry Returns
Date: Friday, October 16
Time: 8:00 PM to 10:00 PM
Location: Arts Garage
Sounds of The Set
Date: Thursday, October 22
Time: 5:30 PM to 8:30 PM
Location: Libby Wesley Plaza
What a Night with Nestor Torres
Date: Friday, October 23
Time: 8:00 PM to 10:00 PM
Location: Arts Garage
Ongoing and Seasonal Highlights
Delray Winter GreenMarket
The GreenMarket is back at Old School Square on Saturdays from 9:00 AM to 2:00 PM, starting October 24. It is the clearest sign the season has started.
Old School Square
Old School Square is the cultural center of downtown, and this month it hosts art openings, the Coco Market, National Night Out, Kidsfest and the GreenMarket. Pair an evening event with dinner along Atlantic Avenue.
Sandoway Discovery Center
The Sandoway Discovery Center on A1A has aquariums, live animal encounters, and programs on sharks, coral reefs and local coastal ecosystems. A reliable option on a rainy afternoon.
Beach and Outdoor Lifestyle in October
October is the first month the heat starts to ease. Afternoon storms become less frequent, mornings are cooler, and outdoor time stretches back into the day. Popular local stops include Delray Municipal Beach, Wakodahatchee Wetlands for birdwatching and boardwalk walks, the Morikami Museum and Japanese Gardens, and the Atlantic Avenue district for walkable, urban-style living.
Community Updates: What Is Happening in Delray Beach This Month
Hurricane Season Is Not Over Yet
Hurricane season runs through November 30, and October storms still happen. If you are buying here, keep working through flood zone designation, wind mitigation credits, roof age and impact window condition on every property you consider. Those items move your carrying cost more than almost anything else in a Florida purchase. Insurance costs vary by property, elevation, roof age, construction type and carrier. Consult your carrier or a licensed Florida insurance agent for a quote on the specific property.
The Beach Recognition Still Stands
The renourishment project completed earlier this year widened the recreational beach and strengthened storm protection. Delray was named Best Beach in Florida in USA Today's 10Best Readers' Choice Awards for the third year running, and Delray Municipal Beach holds Blue Flag designation for the 2026 season.
Halloween Weekend Is a Good Scouting Trip
If you want to see how the downtown community actually works, October 24 shows you more in one day than a week of showings. The GreenMarket, a charity ride, a neighborhood parade and the Avenue full of local families. You see the town at its most local, before the winter visitors arrive.
The Season Is Starting
Fall inventory and competition build from October forward. Buyers targeting a January move are touring now and writing offers before winter pricing returns. Northeast buyers, including many from Bergen and Hudson County, use this stretch to get under contract. If your goal is to be in the home by January, the search starts this month, not in November.
Thinking About Moving to Delray Beach This Fall?
Whether you are considering a second home, an investment property, or a full relocation from Bergen or Hudson County to South Florida, working with an agent who knows both markets makes a real difference. Scott Selleck is a Broker / Sales Associate with The Selleck Group at KW City Views Realty in Fort Lee, New Jersey, and is licensed in Florida through Keller Williams Boca Raton Realty. He helps buyers compare neighborhoods, understand seasonal pricing, and match lifestyle goals to the right Delray Beach community.
Call or text: 201-970-3960
Plan Your Move in Three Steps
Start with the assessment, explore the Florida guides, then dig into the advisory site.
Step 1. Take the Seven-Question Assessment
Seven quick questions, about 90 seconds, and a clear read on where you stand and what your next move should be.
https://quiz.sellecksellsnj.com/
Step 2. Explore the Florida Relocation Guides
Compare Florida towns, regions, cost of living, taxes and insurance. The Delray Beach town guide is here:
https://moving-to-fl.sellecksellsnj.com/florida-towns/delray-beach/
Step 3. Visit the Real Estate Advisory Site
Go deeper on strategy, timing and the full relocation picture.
https://scott.sellecksellsnj.com
Ready to talk through the NJ to FL Transition Plan? Schedule a conversation: https://tidycal.com/slselleck
Scott Selleck, REALTOR, Broker / Sales Associate
The Selleck Group | KW City Views Realty
SRES, e-PRO | Licensed since 1993
2200 Fletcher Avenue, Suite 502, Fort Lee, NJ 07024
Cell or text: 201-970-3960 | Office: 201-592-8900
[email protected] | SelleckSellsNJ.com
Schedule a conversation: tidycal.com/slselleck
AI Assistant: https://www.delphi.ai/scottselleck
Florida: Keller Williams Boca Raton Realty
7280 W Palmetto Park Rd, #110, Boca Raton, FL 33433
Office: (561) 997-0500
NJ Real Estate Broker / Sales Associate #9236275 | FL Real Estate Sales Associate #SL3588731
Keller Williams City Views Realty and Keller Williams Boca Raton Realty. Each office is independently owned and operated.
Equal Housing Opportunity
https://sellecksellsnj.com/blog/equal-housing-opportunity-scott-selleck-and-the-selleck-group-at-kw-city-views-realty
Event details are from the Downtown Delray Beach events calendar as of September 28, 2026 and may change. Confirm times with each venue before you go.
