What To Do This Weekend in the Naples Florida

Looking for things to do this weekend in the Naples Florida? Halloween falls on Saturday, October 31 this year, and the area is celebrating with a full three days: the 5th Avenue South Halloween Spooktacular in Olde Naples, the Día de los Muertos celebration at the Naples Botanical Garden, two Saturday farmers markets, family fall fests, and live music in several corners of town. Here is the verified plan for Friday, October 30 through Sunday, November 1, 2026, organized by day.

Friday, October 30: Trick or Trolley and a Night at Artis-Naples

Friday evening belongs to the grown-ups. The Naples Junior Woman's Club hosts Trick or Trolley, its annual Halloween trolley bar-crawl fundraiser, with check-in from 6:30 p.m. and the ride running 7:30 p.m. to 12:30 a.m. The crawl starts at Bone Hook Restaurant & Brewery, 1514 Immokalee Road Unit 106 in North Naples, where costumed riders board the trolley for a night of stops around town. It is a 21-and-up event, and the ticket proceeds benefit the club's community work, so dress up and ride. Tickets are on Eventbrite's Naples Halloween listings.

If the trolley is not your speed, Artis-Naples on Pelican Bay Boulevard opens its season in style: pianist Yeol Eum Son joins the Naples Philharmonic for a Masterworks program of Beethoven and Brahms on Friday evening at Hayes Hall. The campus also houses the Baker Museum, which is open Saturday and Sunday with the Surrealist International exhibition that opened earlier this month. Full program details, dates, and tickets are on the Artis-Naples events page. The whole complex sits a short drive from the Pelican Bay waterfront.

Make the evening a downtown evening instead: dinner in Olde Naples, where Fifth Avenue South and Third Street South book live music most nights and the walk to the Naples Pier makes a natural after-dinner stroll. It is also the smartest spot to set up for Saturday, when the neighborhood's legendary walkability does the work for you, as my guide to the most walkable Naples neighborhoods explains.

Saturday, October 31: Halloween Day in Naples

Start Halloween day the Naples way: at the farmers market. Third Street South Farmers Market in Olde Naples runs 7:30-11:30 a.m. every Saturday year-round, with produce, flowers, and prepared food along the district's boutique shopping blocks. Twenty minutes north, the Vanderbilt Farmers Market fills the Shoppes at Vanderbilt at 2355 Vanderbilt Beach Road from 8 a.m. to 1 p.m. with more than 90 vendors in peak season. Both are walkable from their surrounding neighborhoods, so grab coffee and market breakfast before the costume chaos begins. See the Third Street South market page and the Vanderbilt market site for details.

Early risers with kids can meet The Naples Players at Sugden Regional Park on Avalon Drive for the Stage Fright Walk & 5K, a Halloween-themed fun run from 8-11 a.m. that benefits the theater's education programs. Costumes are encouraged; the course is friendly to walkers as well as runners. Tickets and details are on the Naples Players ticket page, which also lists opening weekend of the Academy's production of The Addams Family Jr. in the Glass Theater at the Sugden Community Theatre on Fifth Avenue South.

The centerpiece of Halloween afternoon is the 5th Avenue South Halloween Spooktacular, a free family event from 3-5 p.m. at Cambier Park on 8th Avenue South in Olde Naples, with live music, games, and a costume contest. At 5 p.m. it rolls into Halloween Spooktacular Evening on Fifth, when musicians set up along Fifth Avenue South's sidewalks and the shops and restaurants keep the district alive until 8 p.m. The Fifth Avenue South Business Improvement District runs both, and the official Spooktacular page has the full schedule. It all happens in the walkable heart of Olde Naples, where parking fills early on big event days.

Two more family stops round out the afternoon. Fall Fest 2026 runs 1-4 p.m. at the Paradise Coast Sports Complex, 3940 City Gate Boulevard South, with games and activities on the big sports campus. And Fright Night in the City takes over Fleischmann Park at 1600 Fleischmann Boulevard from 5-7 p.m., pairing family Halloween activities with a food truck row. Both are listed on local event calendars and are low-cost ways to stretch the holiday past dinner.

For something richer, Día de los Muertos returns to the Naples Botanical Garden at 4820 Bayshore Drive on both Saturday and Sunday, 10 a.m.-4 p.m. The celebration brings live music, community altars, and artisan vendors into the garden's tropical landscape, with La Catrina flower-crown workshops at 10 a.m. and 2 p.m. ($40). It is a beautiful, respectful way to experience the holiday, and garden admission gets you both days of programming. Tickets and workshop registration are on the Botanical Garden event page.

Halloween night, the live music continues in North Naples: Sounds on Strada at Mercato runs 6-8 p.m. with free live local music in the Piazza, and Live Music Saturdays at the Compass Hotel by Margaritaville starts at 5 p.m. Over in Bonita Springs, The Rockefellers play Sugar Shack Downtown at 1 p.m. if you want a daytime set with your costume.

Sunday, November 1: Garden Day, Brass Band, and the Beach

Sunday is the weekend's slower chapter. The Día de los Muertos celebration at the Naples Botanical Garden runs its second day from 10 a.m.-4 p.m., and with the flower-crown workshops scheduled again at 10 a.m. and 2 p.m., it is worth building the morning around. After the garden, the free Naples Concert Band plays "Italian Masterpieces and American Pride" from 2-3 p.m. at Cambier Park downtown, an easy sit-outside-and-listen way to close the holiday weekend.

Indoors, The Naples Players present the mainstage production Rocket Man with a 2 p.m. Sunday matinee at the Sugden Community Theatre, 701 Fifth Avenue South, and the Baker Museum at Artis-Naples is open Sunday 12-4 p.m. (Saturday 10-4) with the Surrealist International exhibition continuing through February 14, 2027.

And if the holiday left you needing sand and salt air, the water is the best reset. Lowdermilk Beach Park and Delnor-Wiggins Pass State Park are the reliable public choices, and the Naples Pier sunset never misses. My guide to Naples beach access lays out which beaches have parking and how the private beach clubs in Park Shore and Pelican Bay work, which is useful whether you are visiting or scouting the area for a move.

All Weekend: What to Know Before You Go

A few practical notes. Downtown parking in Olde Naples fills early on Halloween, so arrive before the Spooktacular or plan to walk from the residential side streets. Restaurants on Fifth Avenue South and Third Street South take reservations fast on holiday weekends; book ahead. Trick or Treat hours vary by neighborhood, and several communities on the north side schedule their own early door-to-door hours, so check your neighborhood's local association page.

Hockey fans take note: the Florida Everblades are on the road this weekend, playing two games at Greenville, so Hertz Arena in Estero has no home game on October 30 or 31. The team's official site has the full schedule for the weeks ahead.

If you are in town for the weekend and thinking about making Naples a permanent address, this is a great weekend to see the city at full festival energy. My relocation guide to choosing a Naples neighborhood compares the lifestyle, lot, and construction differences between Olde Naples, Pelican Bay, Park Shore, and the rest of the market, and my Naples buyer's guide walks through the process step by step. And if you missed any of it, the previous edition's guide covers the October 16-18 weekend in the archive. Questions about any of it? Get in touch and I will help you sort it out.