Fruitville Grove Annual Pumpkin Festival

Every weekend in October, 7410 Fruitville Road, Sarasota, (941) 377-0896, fruitvillegrovefarm.com

Pumpkins have their own season, so they deserve their own festival. Fruitville Grove will celebrate its 34th Annual Pumpkin Festival every weekend in October from 10 a.m.-5pm on Saturdays and Sundays. Admission includes access to the playground and petting zoo, live music, the Torres Family Circus show, photo ops and costume contests. Visitors can also partake in a variety of rides and activities like zip lining, pumpkin painting, and shopping at vendor booths. Both the farmers market and the Pumpkin Palace will be open, too. Admission is free; parking is $5.

Barks & Brews at the Green at University Town Center

Oct. 11, The Green at UTC, across from Gifts & More at 125 N Cattlemen Rd Unit 101, Sarasota, utcsarasota.com

Every month, our canine companies join us for Barks & Brews at UTC, benefiting Nate's Honor Animal Rescue. The October event will be extra special, as it features a dog costume contest, judged by local celebrities including Sarasota Magazine's editor-in-chief Cooper Levey-Baker. There will also be live music, vendors, and plenty of brews to go around. Barks & Brews runs from 6-8p.m., and the costume contest begins at 7:30p.m. Admission is free. 

Discover Sarasota Tours: Haunted Sarasota “Mummies, Murder, and Mayhem” Tour

Oct. 14-31, 1826 Fourth St., Sarasota, discoversarasotatours.com

Sarasota boasts stunning beaches, great restaurants and...ghosts?! Discover Sarasota Tours invites the bravest souls ages 12 and older on its “Haunted Sarasota Mummies, Murder, and Mayhem” trolley tour. The tour takes guests on a 90-minute nighttime journey through the city's spookiest corners. Guided by the Ghost Hostess, guests will even meet some figures of local lore along the way. Dress up for the costume contest to win exciting prizes. Complimentary liquid courage (beer and wine) is available for guests ages 21-plus from the Trolley Cottage Tiki Bar. Tickets are $49.99; parking is free.

Discover Sarasota Tours: The Boomobile Tour

Oct. 14-30 (weekends only), 1826 Fourth St., Sarasota, discoversarasotatours.com

Discover Sarasota's newest spooky offering is the family-friendly "BooMobile" tour. This 45-minute musical adventure runs from 6:30 p.m.-7:15 p.m. and begins with free apple cider and cookies from the Trolley Cottage. On board, join Miss WitchyPOO on a search around Sarasota for her missing magic pumpkin. If you're in the mood, don a costume—the best one wins a special prize in the costume contest. Tickets for kids ages 3-11 are $19.99; tickets for those 12-plus are $24.99. Parking is free.

Selby Gardens Historic Spanish Point: Lights at Spooky Point

Oct. 14-31, Historic Spanish Point Campus, 401 North Tamiami Trail, Osprey, (941) 366-5731 

This year marks the first "Lights at Spooky Point" at the Selby Garden's Historic Spanish Point. Trek into the woods and meet the weird and wonderful inhabitants that dwell in the darkness. Enjoy pumpkins, a hay maze, and yummy Halloween treats. Choose to enter at 6:30 or 7:45 p.m nightly. For ever more fun, take the Set Sail to Spooky Point boat tour from the downtown campus, available certain nights in October. Find more information about the boat tour online. Admission for "Lights at Spooky Point" is $20 for members, $25 for non-members, $15 for children (5–17), and free for ages 4 and under.

Hunsader Farms

Saturday-Sunday, Oct. 15-16, 22-23, and 29-30, 5500 C.R. 675, Bradenton, (941) 322-2168, hunsaderfarms.com

Hunsader Farms will hold its 31st annual Pumpkin Festival from 9 a.m.-5 p.m. on Saturdays and Sundays during last three weekends in October. Admission includes hay rides, the petting zoo, live music and more. Visitors can also enjoy a corn maze, train rides and a "butterfly experience." Admission is $15; children 10 and under are free. Parking is $5.

Suncoast Science Center/Faulhaber Fab Lab Halloween Workshop

Saturday and Sunday Oct. 15-16, Suncoast Science Center, 4452 S. Beneva Road, Sarasota, (941) 840-4394, suncoastscience.org

Take pumpkin carving to the next level at the Suncoast Science Center's annual Halloween workshop. Activities include laser pumpkin engraving, customized Halloween mask making and even chocolate making. Hourly sessions run Saturday from 2 p.m.-7 p.m. and Sunday from 1 p.m.-4pm. Admission for up to three people is $45 and includes two activity options. 

Halloween Burlesque at McCurdy's Comedy Theatre

Sunday, Oct. 16, McCurdy's Comedy Theatre, 1923 Ringling Blvd., Sarasota, (941)-925-FUNY (3869), mccurdyscomedy.com

Shake up spooky season with some laughs at the Hard Heart Burlesque Halloween special. The event begins Sunday Oct. 16 at 8pm. Enjoy singing, showgirls and more. This event is for adults 18-plus only; tickets are $37.

Boo! At the Bay

Friday, Oct. 21, Civic Green and Municipal Auditorium, 801 N. Tamiami Trail, Sarasota, (941) 203-5316, 10daysatthebay.org

Get in costume and head out to Boo! At the Bay on Friday, Oct. 21. Enjoy trick-or-treating, free pumpkin pickings, yard games, food truck feasts, chances to win prizes, and more from 6-10 p.m. The free, kid-friendly pumpkin art project starts at 5 p.m. and requires registration. Other special events also encourage registration such as the Spooky Moonlight in the Mangroves Tour. Admission is free.

Haunted Trail Carnival at Arlington Park & Aquatic Complex

Friday, Oct. 21, Arlington Park & Aquatic Complex, 2650 Waldemere St., Sarasota, sarasotafl.gov
From 5 p.m.-7 p.m., Arlington Park will transform into a Haunted Carnival Trail. Kids and families can enjoy trick-or-treating, carnival games and more. Admission is free.

Howl-O-Ween Movie Night Spooktacular

Saturday, Oct. 22, Ed Smith Stadium, 2700 12th St., Sarasota, scgov.net
Kids and families are invited to attend the Howl-O-Ween Movie Night Spooktacular on Saturday, Oct. 22. Doors open at 5 p.m., and attendees can play games, visit community booths and partake in other festive fun. Attendees can also join the costume parade on the field with the Orioles’ bird at 6:45 p.m. Starting at 7 p.m. the film Coco will begin. Admission is free, but all are encouraged to bring at least one non-perishable food item for donation to the All Faiths Food Bank.

Second Annual Fall Festival at University Town Center

Saturday and Sunday, Oct. 22-23, The Mall at University Town Center, Parking Lot 4 (East Side), (727) 674-1464, mallatutc.com

The Mall at UTC will host this family-friendly event on Oct. 22-23 from 11 a.m.-6 p.m. Guests can enjoy a pumpkin patch and participate in a pumpkin pageant as well as carnival rides and a pet costume contest. There will also be a vendor market, food and beer trucks, and other fun fall activities. Admission is free.

Trick-or-Treat on the Lake at Nathan Benderson Park

Oct. 25, Regatta Island, 5851 Nathan Benderson Circle, Sarasota, (941) 358-7275, nathanbendersonpark.org

Trick-or-treating is fun, but trick-or-treating by the lake? Spooktacular! Come in your best costume and trick-or-treat on the lake from 5:30 p.m.-8 p.m. Perfect for families, this free event will offer candy booths, live music, a play area and storytelling area, and a special screening of Hotel Transylvania. Admission is free; parking is $10.

Trunk-or-Treat at Good Shepherd Lutheran Church & School

Friday, Oct. 28, Good Shepherd Lutheran Church & School, 5651 Honore Ave, Sarasota, goodshepherdsarasota.org
The Good Shepherd Lutheran Church & School invites everyone to their annual Trunk-or-Treat community event, from 6:30 p.m-8:30 p.m. Participants must register their vehicle for decoration at the school office. Admission is free.

Frightfully Fun Trick-Or-Treat Event at The Mall at UTC

Saturday, Oct. 29, The Mall at University Town Center and outside at the East Grand Entrance, utcsarasota.com
On October 29 from 5:30 pm- 7:30 pm, the Mall at UTC opens its doors for trick-or-treaters. Collect candy throughout the mall and enjoy a dance party, bounce houses, Halloween games and more. Admission is free.

Boo! at The Bazaar

Saturday, Oct. 29, 821 Apricot Ave., Sarasota, (941) 445-1938, bazaaronapricotandlime.com

Trick-or-treaters are invited to dress up and attend this family-friendly event at The Bazaar on Apricot & Lime. The event will take place inside the bazaar and runs from 10 a.m.-3 p.m. Collect candy from each vendor booth, receive a free book and enjoy live music from Sean Adam Walsh. Admission is free.

Boo! at The Bishop

Saturday, Oct. 29, 201 10th St W, Bradenton, bishopscience.org
Step into the past for a night of trick-or-treating from 6 p.m.-9 p.m. at the Bishop Museum of Science and Nature. Show off your costume as you wander through the halls, collecting candy. Admission for “Boo! at The Bishop” is $7 for ages 4-plus, and free for children under 4.

Sarasota Dog-A-Ween Costume Contest

Saturday, Oct. 29, Lemon Avenue and Main Street, downtown Sarasota, destinationdowntownsarasota.com

If you’ve ever bragged about how adorable your dog looks dressed up, then the 14th annual Dog-A-Ween Costume Contest is for you. Beginning at 9 a.m., parade your costumed dog through the Sarasota Farmers Market. All participants will receive a goodie bag from Wet Noses Sarasota, and winners will receive prizes from downtown Sarasota businesses. Registration is $15, and all of the proceeds go to Donte’s Den Foundation. Parking is available at the Whole Foods Market garage.

The Boo Run!

Saturday, Oct. 29, 6300 University Parkway, Sarasota, (941) 893-7589, raceroster.com/events/2022/62435/2022-boo-run

Lace up your sneakers for the 19th annual Boo Run, hosted by the Lakewood Ranch Running Club. The in-person event takes place on Oct. 29 at a new 5k course in Lakewood Ranch. Three options are available, including a kids’ race, adult race and a race with dogs. The event begins at 7:30 a.m., with start times for each race listed here. There will also be a virtual option from Oct. 25-31 in which runners can submit their times. Runners are encouraged to dress up for the event’s costume contest. All proceeds will be split 50/50 between Another Day for Gray and the Humane Society of Lakewood Ranch. For pricing info and registration, click here.

Ghosted: A Halloween Experience

Oct. 29, Oasis Restaurant & Bar, 1525 Fourth St., Sarasota, sarasotaout.com

Ready to get your skeleton dance on? Presented by SarasotaOUT, this Halloween dance party will be held at Oasis Restaurant & Bar from 9 p.m.-2 a.m. The event will feature a costume contest with exciting prizes as well as a drag show. Guests can purchase reserved seating, too. Tickets range from $10 general admission to $25 for VIP access. Click here for more.

Monsters Booze Cruise

Saturday, Oct. 29, LeBarge, 2 Marina Plaza, Sarasota, sarasotaout.com

What do you get when you combine Halloween, Sarasota Bay and alcohol? The Monsters Booze Cruise, presented by SarasotaOUT. The cruise will sail from 9 p.m.-11 p.m., and guests are encouraged to wear their Halloween best for the costume contest. Dancing and drag performances will be accompanied by a DJ. Have no fear: snacks and a bar will also be available. Attendees must be 21 years of age are older. Tickets are $45, with an optional add on to the Oasis afterparty (more info on that above).

Gator Club’s Annual Halloween Block Party

Saturday, Oct. 29, 1490 Main St., Sarasota, thegatorclub.com

The Gator Club’s Halloween block party runs from 6 p.m.-2 a.m. The event will feature a DJ indoors and live music both indoors and outside. There will also be food trucks and vendors. This event is 21-plus. Outdoor admission is free; indoor admission is $20.

Mote A-scare-ium

Oct. 29, 30 and 31, Mote Marine Laboratory & Aquarium, 1600 Ken Thompson Parkway, Sarasota, mote.org

Join Mote mascots Gilly and Shelley during regular aquarium hours (9:30 a.m.-5 p.m.) for under the sea Halloween fun. As always, there will be an ocean of exciting, educational activities for land and sea-dwelling creatures alike. The event will feature trick-or-treating, underwater pumpkin carving and a scavenger hunt. Admission is $19 for ages 3-12, $26 for 13-plus and free for members.

Selby Gardens Spooktacular

Sunday, Oct. 30, 1534 Mound St., Sarasota, (941) 366-5731, selby.org

The Halloween spirit is blossoming at Selby Gardens. This family-friendly event will be held from 10 a.m.-2 p.m. Dress up for trick-or-treating, arts and crafts, and fun educational activities, then dare yourself to brave the inflatable corn maze. Admission is free for Selby Gardens’ members. General admission is $21 for adults, $11 for ages 5-17, and free for 4 and under.

Beneva’s Monster Bash at Mellow Mushroom

Monday, Oct. 31, Mellow Mushroom Sarasota, 6727 S. Tamiami Trail, Sarasota, sarasotaout.com

Groove to the "Monster Mash" at SarasotaOUT’s Beneva’s Monster Bash. This twist on the classic Halloween party takes place Monday, Oct. 31 at 7 p.m. Celebrate spooky season with drag performances, Halloween-themed drinks and spooky games. The event will also feature a costume contest, and the winner will receive free pizza for a year. Due to mature content, this is an adults-only event. Standing room only tickets are $5; reserved table tickets are $10.

Fright Night on St. Armands

Monday, Oct. 31, 431 St. Armands Circle, Sarasota, (941) 388-1554, starmandscircleassoc.com

Even Dracula needs to shop for a new cape—and what better place than St. Armands Circle? This year’s Fright Night will be held Monday, Oct. 31, from 6 p.m.-8:30 p.m. The businesses and restaurants of St. Armands will be spiffed up with spooky decor, promotions and more. Trick-or-treat through the circle, and don’t forget to say “boo” to the costumed statues you meet along the way. Admission is free.