Halloween Events Around Town

This Halloween, there are plenty of occasions for kids and grownups alike to celebrate with a spooky-good time, from traditional bashes like the annual Halloween Spooktacular on 5th to themed treks like the Hallowine Walk.


Thursday, October 27: Hallowine Walk

Presented by the Naples Gulf Shore Sunset Rotary Club, the Hallowine Walk will take place at Mercato from 6-9 p.m. The event will take guests on a tour of the various wine shops throughout the shopping district, and include drinks and bites at over 10 establishments including BURN, Cavo, Naples Flatbread & Wine Bar, Vom Fass, Wine Loft, and The Wine Cellar.

Each guest will receive a commemorative wine glass as well as the opportunity to take red-carpet photos at the registration tent. The event will also include raffle drawings, a passport grand prize, and a costume contest that will begin at 9 p.m.

Tickets cost $50 online and can be purchased here, or $60 at the door. If you buy four tickets, you get one free.

Photo by Glenn Christopher.

Friday, October 28: Boo Bash

An annual family-fun event, the Boo Bash will be held at the Waterside Shops from 5-6:30 p.m. A scary good time, the event includes live music, party favors, trick-or-treating, fantasy characters, jugglers, stilt walkers, and more.

Cost: $10 per child donation benefits the Golisano Children’s Museum of Naples. Space is limited and reservations are required. Click here for tickets.

Friday, October 28-Saturday, October 29: Masa’s Day of the Dead Celebration

Masa‘s popular annual Day of the Dead/Halloween weekend celebration returns this year with festivities including food and beverage specials, sugar skull painting, and live music by Latin rock band Odas from 9-1:30 a.m. both nights. Guests can get into the spirit with delicious appetizers and entrees, $5 Day of the Dead IPA “Hop On or Die” drinks, and $12 Jack-o’-Lantern margaritas made with tequila, fresh lime juice, house-made pumpkin puree, and Mexican cinnamon sticks. Sugar skull painting will be available from 5-9 p.m. on Friday and 7:30-9:30 p.m. on Saturday.



Saturday, October 29: Monster Dash

Gulf Coast Runners’ annual Halloween 5K race will begin at 7:30 a.m. at Fleischmann Park. Everyone is encouraged to wear their favorite Halloween costumes and run wild. Awards, refreshments, and a costume competition will be held immediately following the race.

For more information, call (239) 404-7007 or click here.

Monday, October 31: Halloween Spooktacular on 5th

The sixth annual Halloween Spooktacular on 5th is scheduled from 4:30-9:30 p.m. along 5th Avenue South. An annual family-fun festival, this exciting event will bring kids, teens, and adults together for an afternoon and evening of live music, animal exhibits, kids crafts, costume contests (for all ages and dogs as well), trick-or-treating, a street dance, a giant movie screen, and more.

Photo by Glenn Christopher.

This year’s event features Young Life New Collier as its charity partner. Guests are invited to show their support by making a suggested donation of $5 or more at the entry to the event. For more information and a complete schedule of events, click here.

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