In a town that swaps cornfields for miles of coastline, there’s still an abundance of places and events to find Halloween fun in the Middle Keys. Witches are taking over Crane Point, costumed trick-or-treaters are hitting the beach, and popular neighborhoods are stocking up on candy.
This starts the time of year when keeping the calendar straight is a full-time job – so we’re here to help. Grab a candy bucket, your best costume and the whole family for a frighteningly full October.
What: Lower Keys Rotary Annual Haunted House
When: Friday through Sunday, Oct. 9-11, 8-10 p.m.
Where: Big Pine Key Community Park
Details: Join the Lower Keys Rotary Club for its annual haunted house – “Nighttime Screams & Bad Dreams” at the Big Pine Key Community Park. Built and staffed with help from Rotarians, nonprofits and community volunteers, the house sends guests through a series of themed rooms with actors and Halloween horrors. Food, entertainment and fall activities complete the family-friendly weekend in the park.
What: Witches in the Hammock
When: Saturday, Oct. 17, 6:30-9 p.m.
Where: Crane Point Museum & Nature Center
Details: Join Crane Point for its annual Witches in the Hammock event. Take a lantern walk through the hammock to a haunted house and watch the witches who live there dance around the fire pit. Have some witches’ brew and ride back to the Crane Point courtyard for all kinds of spooky games. Casper’s house will also be open for a visit with the friendly ghost. Admission is $15 for adults and $5 for children. NEW this year, a parade with the witches will ride down Sombrero Beach Road starting at 5:30 p.m.
What: Float-In Movie at the Lagoon
When: Saturday, Oct. 17, 6 p.m.
Where: Marathon Community Park
Details: The city of Marathon and the Lagoon on Grassy Key will show “The Perfect Storm” at dark on a lagoon-side projector screen. Please note that the date is now one week later than originally scheduled (Oct. 10). Sign-in begins at 6 p.m. at 59300 Overseas Hwy. Children 12 and under must be accompanied by an adult at all times, and kids 13 to 17 must have a parent on the premises during the event. Bring a float and life vest to watch from the water, or a chair or blanket to watch from land. Refreshments are available for sale.
What: Trick or Treat at the Beach
When: Friday, Oct. 23, 5:30 to 8 p.m.
Where: Sombrero Beach
Details: Costumed little ones can get their fill of sweets at Sombrero Beach when the city of Marathon hosts its annual Trick-or-Treat at the Beach. Dust off your Halloween best, grab your buckets, and bring the whole family out for a spooktacular evening by the sea featuring plenty of candy, laughs, and Halloween fun. Collect goodies from local groups and businesses who put up displays along the park path. Registration is only required for groups who wish to put up a display or tent. Spaces are limited to a 10- x 10-foot area. Email parksandrecreation@ci.marathon.fl.us to reserve a spot and for additional display rules.
What: Stanley Switlik’s Spooktacular Halloween Carnival
When: Sunday, Oct. 25, 11 a.m. to 2 p.m.
Where: Stanley Switlik Elementary School
Details: Head over to Switlik for the school’s annual Halloween carnival. Feel free to wear a costume and join the parade at 12:30 p.m. The day includes candy, games, food, crafts, music, a bounce house, the famed cake walk, a silent auction and more. Donors and volunteers can contact ptoswitlik@gmail.com.
What: 16th annual City of Marathon Employee Costume Contest
When: Friday, Oct. 30, 9 a.m. – 4 p.m.
Where: City Hall, 9805 Overseas Hwy.
Details: Come see all the employee costumes and cast your votes. Cost is $1 per vote. All proceeds will be donated to Payton’s Promise, a nonprofit sanctuary for underprivileged or special needs dogs nearing the end of life.
What: Boo Bash Costume Contest
When: Friday, Oct. 30, 6 p.m. (costume contest 7 p.m.)
Where: Havana Jack’s Oceanside Restaurant, 401 E Ocean Dr., Key Colony Beach
Details: Cool prizes and bragging rights are up for grabs at the 2026 Boo Bash Costume Contest. Come in your best costume and prepare for a night of spooky fun as you fight for top marks on the judges’ score cards. All ages welcome. Proceeds go to benefit Presents in Paradise, which helps local working families provide Christmas for their kids. Live music, a 50/50 raffle, celebrity judges and scary drink specials will combine to guarantee a frighteningly fun evening.
What: Halloween Kids Costume Run
When: Saturday, Oct. 31, 9 a.m.
Where: 1155 Bulevar de Palmas, Marathon
Details: HapynKeys Running’s annual Halloween costume run is back. The 1-mile run will take participants around a local neighborhood loop, and the event will include refreshments, snacks, medals for all runners, and best-costume and top-runner prizes.
What: Trick or Treat at Aquarium Encounters
When: Saturday, Oct. 31, 9 a.m.
Where: Aquarium Encounters, 11710 Overseas Hwy.
Details: Kids in costume will receive free admission to Aquarium Encounters and candy with a paying adult or member. Trick or treat and play games at the exhibits at the aquarium. While supplies last.
What: Gulfside Village Trick or Treat
When: Saturday, Oct. 31, 5:30 – 7:30 p.m.
Where: Gulfside Village, 5800 Overseas Hwy.
Details: Annual Trick or Treat Halloween party at Gulfside Village. Come enjoy the fun in the fresh outdoors. Candy donations are appreciated and can be dropped off at Flowers By J&J. Any business or organization that would like to set up a table or donate candy may contact Flowers By J&J to reserve a spot. Call 305-743-5459 or email danielle@keysflowers.com.
What: Grassy Key Halloween
When: Saturday, Oct. 31, 5:30 p.m.
Where: Grassy Key on Goodley, Gibson, Bailey and the west end of Morton Street.
Details: Please join the Grassy Key community in passing out candy for trick-or-treaters. All are welcome. Neighbors from outside the listed streets are welcome to set up trick or treat tables at Sunset Park on Morton Street.
What: Trick or Treating Behind the Airport
When: Saturday, Oct. 31, starting at dark
Where: Neighborhood off Aviation Boulevard between Dolphin Drive and Harbor Drive.
Details: Come join the fun for Marathon’s traditional behind-the-airport trick-or-treating. MCSO deputies will be controlling traffic in the area from 6 to 11 p.m. A one-way traffic pattern will be established according to the map shown here. Parking is prohibited on Aviation Boulevard, but ample parking is available on Gulfstream Boulevard.
