Catch a Fright in Siesta Key This Halloween with These Spooky Activities!

January 23, 2026

Are you heading to Siesta Key this Halloween season for a frighteningly good time? Among the many things to do in Siesta Key during this time of year are visiting haunted houses, going on ghost tours, and looking at spooky displays. Other Siesta Key Halloween events include craft festivals, pumpkin picking, and of course, trick-or-treating.

So, pack your costume along with your bathing suits and beach towels, select your accommodations from among many Siesta Key vacation rentals, and get ready to enjoy the surf, sand…and scares!

Haunted come right in sign
Photo: Unsplash

 

 

Haunted Houses/Ghost Tours

Though of course, well known for sun, spectacular white sand beaches, blue waters, and more, Siesta Key and downtown Sarasota reveal their darker sides come Halloween. Among the Siesta Key things to do during the Halloween season are ghost walks, tours, and visits to haunted locales.

Let’s take a look at some of the dark doings in and around Siesta Key that will make your Halloween visit there a real SCREAM.

Mummies, Mayhem & Murder

The enclosed, air-conditioned trolley is a fun and free way to get around Siesta Key, but on some nights before and on the night of Halloween, this turns into an interactive haunted tour sure to be enjoyed by the whole family.

Your narrator—or rather, Ghost Hostess—will spin stories of actual murders and unsolved crimes from the area while relating the history of Sarasota during this 90-minute trip.

Come dressed in costume, as there are prizes for Best Costume every night in October! Complimentary beer or wine is served at the Trolley Cottage Tiki Bar prior to the start of the tour. Tour is designed for ages 12-adult; ages 12-20 must be accompanied by an adult or guardian.

Tombstone Tour

Let’s face it: graveyards can be scary, whether in person or on video, even more so during the Halloween season. The walking tour hosted by the Manatee Village Historical Park is an effectively spooky Halloween event.

The tour is of the 1850 Manatee Burying Ground and you’ll learn not only of the cemetery’s history but about some of the individuals buried there. You’ll also be schooled about the meaning of tombstone symbols.

Guided tours begin October 8th, 2022 and last through October 22, 2022. These morning tours are free and available on a first-come, first-serve basis.

Ghosts & Gruesomes

The “#1 creepy walking tour of Sarasota,” Ghosts & Gruesomes is a Siesta Key Halloween event not to be missed!

During the 75-minute, after-dark tour, you’ll hear about historic area murders, paranormal activities in the town’s theater district, and maybe even catch an orb or other apparition on your camera as you walk the shadowed streets with your tour guide.

There’s simply not a ghost of a chance that you do not thoroughly enjoy this chilling walking tour, which runs weekends throughout the year, but increases to three nights per week as well from mid-September through December. Reservations are needed to attend this tour.

Lights & Displays

Just because it’s not cold and windy, with the dry whisper of fallen autumn leaves drifting across the sidewalks, doesn’t mean Siesta Key doesn’t deck itself out in Halloween lights and displays for this ghostly season.

One of the most animated and exciting displays you might come across in the area is at 133 South Lime Avenue in Sarasota, a cul-de-sac where the local artists of Enlightened Monkey Arts feature a large projection and animatronics of monsters, spiders, and even a cemetery. Where else can you go to see fire-breathing pumpkins, light-up skull flowers, and glowing spider eggs? Creepy sounds and special effects further highlight this stunning drive-through display, one you will simply die for!

Festivals

From pumpkins to parades, there are several Halloween-themed festivals taking place in Siesta Key and Sarasota during the fall season.

The Annual Hunsader Farms Pumpkin Festival, now in its 31st year, has everything from crafts and games to scarecrow displays, hayrides, and a rock-climbing wall. You’ll find face painting, bounce houses, a costume contest, and more at the 20th Annual Goblin Gathering at GT Bray Park. The Selby Gardens Spooktacular has pumpkin decorating and trick or treating. And there are plenty of games and a parade in addition to a costume contest at the Halloween Trail Carnival at Arlington Park and Aquatic Complex in Sarasota.

Even an area large-animal sanctuary, Big Cat Habitat, gets in on the Halloween action! Pumpkin painting, pumpkin bowling, and mummy wrapping contests are just some of the fun activities you can enjoy at the Wild-O-Ween. There are also pony rides and a live animal demonstration!

A popular shopping and dining spot, St. Armands Circle, hosts an annual Halloween event as well:

Fright Night on St. Armands

Entering its 14th year, Fright Night on St. Armands is among the most engaging Halloween Siesta Key events you can partake in.

Spookily decorated storefronts. Costumed figures like zombies and werewolves popping up from around corners. Tons of candy is given out by restaurant and shop owners. If you really want to get into the spirit of Halloween, St. Armands is definitely the place to be and to bring your kids for a memorable night of tricks, treats, and terrifying fun.

Plan Your Visit

Siesta Key Luxury Rental Properties offer the best in Siesta Key rentals, with Gulf views and 3 – 5+-bedroom vacation cottages, condos, and houses (NOT haunted) complete with fully equipped kitchens, decks, covered patios, on-site pools, included beach chairs, and beach towels, and so much more.

Another plus about these Siesta Key rentals is that you’re not far from shops, restaurants, and other attractions, including many of the festivals and tours detailed here. You’re sure to find these Siesta Key vacation rentals and the fun Halloween activities in the area wickedly accommodating and exciting for mummy, daddy, and the whole family.

Pumpkin Patches

Pumpkin patches might not be in abundance in Siesta Key come the spooky season, but that doesn’t mean you can’t find a few; one that comes to mind is the Pumpkin Splash! at Arlington Park & Aquatic Complex, where you can not only enjoy a swim but where you can pick and decorate or carve your own pumpkin!

By far, one of the most popular events in Sarasota during the early fall season is the Fruitville Grove Pumpkin Fest, where you’ll find, among many other things, a pumpkin patch.

Fruitville Grove

Heading into its 34th year, the Fruitville Grove Pumpkin Fest not only lets you pick and paint your own pumpkin at the pumpkin patch (where you can also take family photos), but you and the kids can also spend the day getting your face painted, riding a pony, jumping on a hayride, petting animals in a petting zoo, taking a ride on a mini-train, playing at the game booths, experiencing a butterfly garden, and listening to live music.

There’s also a children’s costume contest held every Saturday throughout October in front of the animal barn.

The pumpkin patch and farm market at Fruitville Grove are open weekly from 9 a.m. – 6 p.m., where you can buy fresh produce and fall decorations and pick yourself a pumpkin for carving.