A Slightly Spooky October on the Gulf Coast: Boo! at The Bay, Venice's Witches Walk & My Evening Picks — Coastal Living Blog
Julie Papagni
Julie Papagni
Julie Papagni
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A Slightly Spooky October on the Gulf Coast: Boo! at The Bay, Venice's Witches Walk & My Evening Picks
Lifestyle 5 min read

A Slightly Spooky October on the Gulf Coast: Boo! at The Bay, Venice's Witches Walk & My Evening Picks

Julie Papagni
Julie Papagni
October 1, 2026 · Updated October 1, 2026

October on the Gulf Coast is festive rather than frightening, and that is exactly how I like it. The evenings turn cool enough for a light sweater, the lights come up along the bayfront, and the calendar fills with ways to enjoy the season without ever needing snow gear. Here is my local plan for the month, from the not-so-scary celebration at The Bay to the grown-up halls of Venice.

Boo! at The Bay: The Month's Signature Night

The one I mark on the calendar first is Boo! at The Bay, the Halloween celebration at The Bay Park on the Boulevard of the Arts, on Saturday, October 17 from 5 to 7:45 p.m. It is an unhurried evening by design: not-so-scary trick-or-treating, free pumpkin picking, yard games, and a movie under the stars as the bayfront darkens, with costumes encouraged for anyone who wants to join in. The rain date is October 24, and the whole event is free, presented by the Gulf Coast Community Foundation.

A Ghoulish Gathering Mid-Month

A week before that, the Venice Symphony leans into the season with its Halloween concert weekend, A Ghoulish Gathering, on Friday and Saturday, October 9 and 10. It is a fun reason to dress up, hum along, and spend the evening in the historic district before the crowds of late October arrive.

The Witches Walk & the Halloween Strut

Downtown Venice keeps the season going in style. On Friday, October 23, the Witches Walk runs 5 to 7 p.m. through the historic streets, an evening the organizers bill as one for the grown-ups, with the shops and sidewalks all in on the theme. Then on Saturday, October 31, the Downtown Halloween Strut brings trick-or-treating to participating businesses along Tampa, Venice and Miami Avenues from 4 to 5:30 p.m., plus a Trunk-or-Treat with a DJ at the Merchants of Venice parking lot at 200 Miami Avenue West. The best part: it all happens the same weekend as the 38th Annual Downtown Venice Art Festival, when West Venice Avenue turns into an outdoor gallery on October 31 and November 1. Costumes in the morning, art in the afternoon, candy on the way home.

The Rest of My October Evenings

Woven through it all are the month-long rituals: Lights at Spooky Point glows through Historic Spanish Point in Osprey every evening through October 31, and Sun Fiesta takes over Centennial Park October 16 through 18 with music, food tents and the classic bed races. The complete lineup, with dates and details, is in my Community Events guide.

If this is the kind of monthly rhythm you want to live with, October is a wonderful month to tour the area. Reach out and I will help you plan the visit, and show you the communities that sit right in the middle of it all.

Julie Papagni — Broker Associate, eXp Realty
Written by

Julie Papagni

Broker Associate with eXp Realty and a proud Palmer Ranch local. Julie relocated from Michigan and now calls the Gulf Coast home. She knows the area inside and out — from the best beaches to the hottest restaurant openings. Have a question or want to chat about real estate? She'd love to hear from you.

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