October 2, 2026 · Lifestyle

What's Happening in Palm Beach County: October 19 through November 1

By Kristi Ramella | South Florida Downsizing Specialist

South Florida downtown avenue at dusk with glowing string lights over Mediterranean storefronts, carved pumpkins and mums in sidewalk planters, and royal palm trees lining the curb

These are the two weeks of the year when Palm Beach County pulls out all the stops for Halloween. From the legendary Witches of Delray bike ride on Saturday morning to a 64-year-old costume parade down Atlantic Avenue, from haunted houses at the fairgrounds to a free waterfront festival on Halloween day in West Palm Beach, the season builds to one big, joyful celebration. Over the fourteen days from October 19 through November 1, you can cheer on the FAU Owls at their Homecoming game, hear rock legends at iTHINK, wander the greenmarkets, and watch thousands of neighbors in costume ride for a cause. Whether you have called this county home for years or you are imagining what a move here could feel like, here is exactly what is coming up in Boca Raton, Delray Beach, and across Palm Beach County.

What's happening this week, October 19 through 25?

This week belongs to the neighbors. The Witches of Delray take over downtown on Saturday morning for a beloved charity ride, Kidsfest and the 64th Annual Halloween Parade fill Old School Square in the afternoon, FAU plays its Homecoming game in Boca Raton, and the fairgrounds open their haunted attractions for the final stretch of the season.

Tuesday, October 20

Breaking Benjamin, Chevelle & Starset at iTHINK Financial Amphitheatre
6:00 PM at 601-7 Sansburys Way, West Palm Beach. Tickets through Live Nation. An evening of hard rock and alt-metal headliners under the stars, one of the big amphitheater shows of the late-fall calendar. Parking lots open early, so go ahead and make an afternoon of it.

Wednesday, October 21

Delray Marketplace Music Fest
6:00 PM to 8:00 PM at the Delray Marketplace Amphitheater, 4664 W Atlantic Ave. Free admission. The Wednesday-evening concert series continues with live music among the shops and restaurants of the Delray Marketplace. Bring a chair, grab a bite, and enjoy dinner and music in the open air.

Thursday, October 22

Clematis by Night, West Palm Beach Waterfront
6:00 PM to 9:00 PM on the Great Lawn at 101 N Clematis St. Free admission. Florida's longest-running free concert series continues every Thursday with live music, food trucks from 5:30 PM, and that unmistakable waterfront glow. The countdown to Halloween has begun, and the city's October editions are always a little extra festive.

Wellington Food Truck & Music Series
Food trucks from 5:00 PM to 9:00 PM, live music from 6:30 PM at Wellington Amphitheater, 12100 Forest Hill Blvd. Free admission. Another Thursday of rotating food trucks and live bands in an easygoing outdoor setting.

Friday, October 23

Art After Dark, Norton Museum of Art, West Palm Beach
5:00 PM to 10:00 PM at 1450 S Dixie Hwy. $10 for adults and seniors, $5 for students, free for members. The Norton's Friday-night tradition of live music, pop-up gallery talks, and a cash bar is one of the most elegant ways to ease into the weekend. Wander the galleries in the evening light, then linger with friends in the museum's gardens.

Fright Nights Opener Weekend, South Florida Fairgrounds
Thursday through Saturday (Oct 22-24): Thursday 6:00 PM to 11:00 PM, Friday and Saturday 6:00 PM to midnight at 9067 Southern Blvd, West Palm Beach. South Florida's premier haunted attraction brings four haunts, carnival rides, games, and live entertainment. Tickets available through the fairgrounds, and the crowds only grow as Halloween approaches.

Spookyville at Yesteryear Village
Opens October 23 and runs nightly through October 31 at the South Florida Fairgrounds, 9067 Southern Blvd. A family-friendly drive-thru Halloween tradition with trick-or-treating, costume contests, a petting zoo, a DJ, and a balloon twister, plus costume parades on Sundays. No scare tactics here, just old-fashioned fall fun for the whole family.

Halloween Glam Bingo, Lake Clarke Shores
7:00 PM at the Compass Community Center, 7485 Community Drive in Lake Clarke Shores. A playful Halloween-themed bingo night, a fun, social way to meet neighbors near the water.

Saturday, October 24

The Witches of Delray Bike Ride, Delray Beach
7:00 AM to 11:00 AM, with the ride departing at 8:00 AM from Delray Beach City Hall, 100 NW 1st Ave. The 15th annual BETR Project's Witches of Delray ride, presented with The Colony Hotel, sends hundreds of costumed riders on a scenic course along Atlantic Avenue and through historic downtown, ending with Halloween festivities and an awards ceremony at Old School Square. It has raised more than $223,000 for the Achievement Centers for Children & Families since 2012, and every witch, wizard, and broom-decorated bike you see is raising money for kids in our own community. Come early to watch the spectacle, or join the ride yourself.

Halloween in Downtown Delray: Kidsfest, Trick-or-Treating & the 64th Annual Halloween Parade
Kidsfest runs 11:00 AM to 3:00 PM at Old School Square, 51 N Swinton Ave. Free and family-friendly. Trick-or-treating along Atlantic Avenue runs from about 11:30 AM to 1:00 PM, and the Rotary Club's 64th Annual Halloween Parade steps off at 1:00 PM from NE 5th Avenue, ending at Old School Square. This is Delray at its most charming: thousands of costumed kids, proud grandparents, and the whole downtown out on the Avenue.

FAU Owls vs. Rice, Homecoming Game, Boca Raton
Flagler Credit Union Stadium on the FAU campus. The Owls host Rice for Homecoming weekend, a campus-wide celebration of the season with tailgating, bands, and school pride. Kickoff time is announced close to game day, so check the FAU athletics schedule in the days before.

Fright Nights and Spookyville, South Florida Fairgrounds
Saturday night is prime time for both: Fright Nights from 6:00 PM to midnight for brave souls, and Spookyville's family-friendly drive-thru for everyone else.

Bedner's Farm Fall Festival, Boynton Beach
9:00 AM to 5:00 PM at 10066 Lee Rd, Boynton Beach. The working farm's fall festival runs daily through November 1, with pumpkin picking, a corn maze, unlimited audio tractor tours, an animal park, and farm food. Admission has run about $21 to $26 per person in recent seasons, with children 2 and under free. A perfect multi-generation Saturday outing.

Delray GreenMarket, West Palm Beach GreenMarket & Lake Worth Beach Waterside Farmers Market
All three Saturday markets return: Delray at Old School Square from 9:00 AM to 2:00 PM, the West Palm Beach GreenMarket on the Great Lawn from 8:30 AM to 1:30 PM with 130-plus vendors, and the Lake Worth Beach Waterside Farmers Market at Old Bridge Park from 9:00 AM to 1:00 PM.

Sunday, October 25

Boca Farmers Market
9:00 AM to 1:00 PM at the Boca Raton Innovation Campus, 4950 Communication Ave. Free admission. Over 85 vendors selling fresh produce, artisan breads, local honey, organic meats, and handcrafted goods, year-round and rain or shine.

Boca GreenMarket
9:00 AM to 1:00 PM at the 5th Ave Shops, 1954 NE Fifth Ave. Boca Raton's original downtown green market with local produce, baked goods, and artisans in a relaxed village setting.

The Gardens GreenMarket, Palm Beach Gardens
8:00 AM to 1:00 PM at 10500 N Military Trail. Over 60 vendors with live music from 9:00 AM to noon. A beloved Sunday-morning ritual with seasonal produce and good coffee.

Bedner's Farm Fall Festival
Another Sunday of pumpkins, corn mazes, and tractor tours at the Boynton Beach farm from 9:00 AM to 5:00 PM.

What about October 26 through November 1?

Halloween week itself brings the biggest celebrations of the season: a free waterfront festival on Halloween morning in West Palm Beach, Haunted Mizner in Boca Raton, the final nights of Fright Nights, and one last weekend of trick-or-treating at Spookyville. The greenmarkets keep rolling, and the Sunday markets close out the month in fine style.

Wednesday, October 28

Delray Marketplace Music Fest
6:00 PM to 8:00 PM at the Delray Marketplace Amphitheater, 4664 W Atlantic Ave. Free admission. Another Wednesday of live music in the open air among the shops and restaurants of Delray Marketplace.

Thursday, October 29

Clematis by Night, West Palm Beach Waterfront
6:00 PM to 9:00 PM on the Great Lawn at 101 N Clematis St. Free admission. The Thursday-night ritual rolls into Halloween. In recent years the city has turned this edition into a costume celebration with Trick-or-Truck candy trucks alongside the live music, so bring the grandkids and dress up if you like.

Wellington Food Truck & Music Series
Food trucks from 5:00 PM to 9:00 PM, live music from 6:30 PM at Wellington Amphitheater. Free admission. Another Thursday of rotating trucks and live bands in the open air.

Fright Nights, South Florida Fairgrounds
6:00 PM to 11:00 PM. One more Thursday night of the fairgrounds' four haunted attractions before the big weekend finale.

Friday, October 30

Art After Dark, Norton Museum of Art, West Palm Beach
5:00 PM to 10:00 PM at 1450 S Dixie Hwy. $10 for adults and seniors, $5 for students, free for members. Live music, pop-up gallery talks, and a cash bar in an elegant evening setting, one of the last Art After Dark nights before the November rush of high-season programming.

Fright Nights Final Weekend
Friday, October 30 from 6:00 PM to midnight at the South Florida Fairgrounds. If you have been working up the nerve all month, tonight and tomorrow are your last chances.

Spookyville at Yesteryear Village
Continues its nightly run through the fairgrounds' holiday stretch, family-friendly trick-or-treating and costume fun all evening.

SOMething Scary at Space of Mind, Delray Beach
6:00 PM to 10:00 PM at Space of Mind, 700 SE 5th Ave. A family-friendly Halloween celebration with creative activities, games, and seasonal fun, a warm neighborhood event for all ages.

Saturday, October 31: Halloween

LagoonFest 2026, West Palm Beach Waterfront
8:30 AM to 2:00 PM along Flagler Drive at the West Palm Beach Waterfront. Free admission. The 13th annual celebration of the Lake Worth Lagoon brings wildlife presentations, a Lagoon Creatures costume contest, a mascot parade, a Kids Zone, and kayak tours of the waterway itself. Put on your most creative aquatic costume and spend Halloween morning on the water before the evening's festivities begin.

Haunted Mizner 2026, Boca Raton
5:00 PM at 590 E Plaza Real, Mizner Park. Boca's Halloween night takes over the amphitheater grounds with costumed fun in one of the most beautiful outdoor settings in the county.

Fright Nights Final Night
Saturday, October 31 from 6:00 PM to midnight at the South Florida Fairgrounds. The season's last scare, and Halloween night is always the most enthusiastic crowd of the year.

Spookyville at Yesteryear Village
The final night of the family-friendly drive-thru Halloween run, a last chance for costume contests and candy before the season closes.

Saturday GreenMarkets
The Delray GreenMarket (9:00 AM to 2:00 PM), West Palm Beach GreenMarket (8:30 AM to 1:30 PM), and Lake Worth Beach Waterside Farmers Market (9:00 AM to 1:00 PM) all run their regular Halloween-morning markets, perfect for grabbing treats for the evening ahead.

Sunday, November 1

Boca Farmers Market, Boca GreenMarket & The Gardens GreenMarket
The Sunday markets return in full: Boca Farmers Market at BRiC from 9:00 AM to 1:00 PM with 85-plus vendors, Boca GreenMarket at the 5th Ave Shops from 9:00 AM to 1:00 PM, and The Gardens GreenMarket in Palm Beach Gardens from 8:00 AM to 1:00 PM with live music from 9:00 AM to noon.

Bedner's Farm Fall Festival, Final Day
November 1 is the last day of the fall festival at 10066 Lee Rd, Boynton Beach, from 9:00 AM to 5:00 PM. If you have not made it out for pumpkins, the corn maze, or the tractor tours yet, this is the closing weekend.

What weekly events should you have on your radar?

Beyond the dates above, these recurring events give Palm Beach County its year-round rhythm:

  • Clematis by Night - Every Thursday, 6 PM to 9 PM on the West Palm Beach Waterfront. Free live music and food trucks. The longest-running free concert series in Florida.
  • Wellington Food Truck & Music Series - Every Thursday, food trucks 5 PM to 9 PM, music at 6:30 PM at Wellington Amphitheater. Free admission.
  • Delray Marketplace Music Fest - Wednesday evenings, 6 PM to 8 PM at the Delray Marketplace Amphitheater, free live music all fall.
  • Art After Dark at Norton Museum - Every Friday, 5 PM to 10 PM. $10 for adults and seniors, $5 for students, free for members.
  • Boca Farmers Market - Every Sunday, 9 AM to 1 PM at BRiC (4950 Communication Ave). Over 85 vendors. Year-round, rain or shine.
  • Boca GreenMarket - Every Sunday, 9 AM to 1 PM at the 5th Ave Shops, 1954 NE Fifth Ave. October through May.
  • The Gardens GreenMarket - Every Sunday, 8 AM to 1 PM at Palm Beach Gardens City Hall (10500 N Military Trail). Over 60 vendors with live music.
  • Delray GreenMarket - Every Saturday, 9 AM to 2 PM at Old School Square (51 N Swinton Ave). October through May.
  • West Palm Beach GreenMarket - Every Saturday, 8:30 AM to 1:30 PM on the Great Lawn at 100 N Clematis St. Over 130 vendors. October through May.
  • Lake Worth Beach Waterside Farmers Market - Every Saturday, 9 AM to 1 PM at Old Bridge Park, October through April.

Why does Palm Beach County work so well for empty nesters and retirees?

The question I hear most often from people considering a move to South Florida is a simple one: "Will I find my community here?" And there is no better answer than a Saturday like October 24 in Delray Beach.

Picture it. At 8:00 AM, hundreds of costumed riders on decorated bikes stream out of Delray Beach City Hall for a charity ride that has raised more than $223,000 for local kids since 2012. By 1:00 PM, the 64th Annual Halloween Parade is marching down Atlantic Avenue past families three generations deep. College students are tailgating for FAU Homecoming in Boca Raton at the same hour, and the fairgrounds are filling up with haunted houses and family pumpkin fun. That is not a special occasion. That is a normal Saturday in Palm Beach County in October.

These are not tourist attractions. They are the fabric of a community built around connection, culture, and quality of life. For empty nesters making the decision to downsize and relocate, that fabric is everything. When you choose a home in South Florida, you are not just picking a floor plan or a zip code. You are choosing a place where it is genuinely easy to stay active, stay curious, and stay surrounded by people who share your enthusiasm for this chapter of life.

On the practical side, Palm Beach County continues to offer compelling advantages for retirees. Florida has no state income tax and no Social Security tax. The homestead exemption can reduce your taxable property value by up to $50,000. The Save Our Homes amendment caps annual assessment increases at 3 percent once you establish residency. Homeowners aged 65 and older with qualifying household incomes may be eligible for additional exemptions. Healthcare is excellent, with Baptist Health Boca Raton Regional Hospital, Delray Medical Center, and Palm Beach Gardens Medical Center all providing nationally recognized care close to home.

More than two dozen 55-plus communities across the county offer active, amenity-rich lifestyles with clubhouses, pools, fitness centers, pickleball courts, and social calendars of their own. And with the Brightline station in Boca Raton providing rail access to Miami and Orlando, getting anywhere you want to go is effortless.

Your quick-reference event list for October 19 through November 1

This week: October 19-25

  • 20
    Tue Oct 20 - Breaking Benjamin, Chevelle & Starset at iTHINK, 6 PM, tickets via Live Nation
  • 21
    Wed Oct 21 - Delray Marketplace Music Fest, 6-8 PM, free
  • 22
    Thu Oct 22 - Clematis by Night, WPB Waterfront, 6-9 PM, free; Fright Nights opens
  • 23
    Fri Oct 23 - Art After Dark, Norton Museum WPB, 5-10 PM, $10; Spookyville opens
  • 24
    Sat Oct 24 - Witches of Delray Bike Ride, 8 AM from City Hall; Kidsfest & Halloween Parade, Delray; FAU Homecoming vs Rice; Bedner's Farm
  • 25
    Sun Oct 25 - Boca Farmers Market, 9 AM-1 PM; Boca GreenMarket; The Gardens GreenMarket

Next week: October 26 - November 1

  • 28
    Wed Oct 28 - Delray Marketplace Music Fest, 6-8 PM, free
  • 29
    Thu Oct 29 - Clematis by Night with Halloween edition, WPB Waterfront, 6-9 PM, free
  • 30
    Fri Oct 30 - Art After Dark, Norton Museum WPB, 5-10 PM, $10; SOMething Scary at Space of Mind, Delray
  • 31
    Sat Oct 31 - LagoonFest, WPB Waterfront, 8:30 AM-2 PM, free; Haunted Mizner, 5 PM; Fright Nights finale
  • 1
    Sun Nov 1 - Boca Farmers Market, 9 AM-1 PM; The Gardens GreenMarket; Bedner's Farm final day

Thinking about making Palm Beach County your home?

If reading through this list stirs something in you, whether it is excitement, curiosity, or the quiet sense that this is the kind of life you have been waiting for, I want you to know that it is closer than you think. I know because I made the move myself, from Ohio to South Florida, carrying all the same questions and uncertainties you might be holding right now. And I have spent the last 25-plus years helping families make the same transition.

The decision to downsize and relocate is one of the biggest life changes you will ever make. But it is also one of the most rewarding. The freedom, the community, the cultural richness, the daily access to beauty and connection, all of it is real, and all of it is waiting for you here.

Whether you are just beginning to explore the idea of downsizing, you want to tour 55-plus communities in Boca Raton or Delray Beach, or you simply want someone who understands the process to walk you through the financial side of the decision, I am here for that conversation. No pressure. No sales pitch. Just honest, experienced guidance from someone who has walked this path many times.

Let's talk about your next chapter.

Book a free, no-pressure Downsizing Strategy Session and let's talk about what your South Florida lifestyle could look like. I will help you understand the communities, the costs, and the process without any pressure.

Kristi Ramella
(561) 778-7198 · ramellagroup@exprealty.com
eXp Realty · SL 3371379

Published October 2, 2026 · Last updated October 2, 2026

Kristi Ramella is a South Florida downsizing specialist with 25+ years of real estate experience and a personal journey of relocating from Ohio. She helps empty nesters and retirees navigate downsizing with confidence, clarity, and compassion.

Ready to start your Palm Beach County lifestyle?

Download the free South Florida Downsizing Guide or book a one-on-one strategy session to get started.

The Downsizing Insider: Free Monthly Tips