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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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).
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.
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.
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.
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.