Sarasota's Spooky Season: 30+ Events You Can't Miss This October

Welcome to October in Sarasota! This October 2023, the beautiful city of Sarasota is home to some of the best events and festivals of the year. From Halloween events to fall festivals and so much more, there is something for everyone this month. Whether you're in Sarasota, Lakewood Ranch, Bradenton or beyond, come out and experience the best of what the area has to offer this October! Get ready for a month of exciting events and festive fun. Let's get started exploring the amazing activities happening in Sarasota this fall!

Sarasota Ski-A-Rees Water Ski Show

October 1st, 2pm | Behind Mote Aquarium

Don't miss the Sarasota Ski-A-Rees Water Ski Show! This exciting event is free and is the first show of the season. Grab your friends and family and head to the ski show every Sunday through November 5th. Watch in awe at 1602 Ken Thompson Parkway as talented skiers showcase their skills and perform jaw-dropping stunts on the water. It's a thrilling experience that you won't want to miss!

35th Annual Fruitville Grove Pumpkin Fest

Every Weekend in October 10am-5pm | Fruitville Grove

Looking for some festive fun in Sarasota this October 2023? Look no further than the 35th Annual Fruitville Grove Pumpkin Fest! This beloved event takes place every Saturday and Sunday in October on September 30th & October 1st, 7th & 8th, 14th & 15th, 21st & 22nd, and 28th & 29th, offering multiple opportunities to join in on the excitement.

The best part? Admission to the fest, along with the petting zoo, playground, live music, Torres Family Circus, and even the costume contests, is completely free! For those looking to indulge in some individual activities, such as pony rides, rock climbing, bounce houses, or pumpkin painting, there is a small fee ranging from $1 to $10. Don't miss out on this must-attend event, and add it to your list of things to do in Sarasota this October!

Phillippi Farmhouse Market

Starting October 4th, 8am-1pm | Phillippi Estate Park

Looking for some mid-week fun in Sarasota this October 2023? Look no further than the Phillippi Farmhouse Market! Open every Wednesday from 8am to 1pm at Phillippi Estate Park, this market is a must-visit for locals and tourists alike. With over 50 vendors offering a variety of produce, plants, prepared foods, specialty items, and sustainable products, there's something for everyone to enjoy. It's a great opportunity to support local growers and producers while indulging in delicious treats. So, if you're looking for things to do in Sarasota, make sure to check out the Phillippi Farmhouse Market!

Paint the Town Fresh Block Party

October 6th, 7pm-10pm | Downtown Sarasota Main Street

Fresh Fridays Downtown Sarasota is hosting a block party that you won't want to miss! Join in for the Paint The Town Fresh event, where you can indulge in local eats from downtown restaurants, have fun and play games, and even score some signature giveaways. And that's not all! They're bringing back The Brett Foreman Band, who were a hit last time. Best of all, this event is completely free and open to the public. So, mark your calendars and come out to enjoy all the festivities. It's one of the top things to do in Sarasota this month!

The 25th Annual Cortez Nautical Flea Market

October 7th, 8am-12pm | Florida Maritime Museum

Get ready for a day of fun and shopping at the 25th Annual Cortez Nautical Flea Market! Held at the Florida Maritime Museum & Cortez Cultural Center, this family-friendly event is free and open to the public. With a variety of vendors selling nautical items, boating and fishing supplies, and more, you're sure to find something that catches your eye. So grab your friends and family and come join in for a day of maritime treasures and excitement at the Cortez Nautical Flea Market!

27th Annual Downtown Sarasota Craft Festival

October 7th-8th, 10am-5pm | Five Points Park

Get ready for a craft lover's dream at the 27th Annual Downtown Sarasota Craft Festival! Located in Selby Five Points Park, on Central and First Street, this festival is the place to be for unique handmade items. From stunning jewelry to exquisite pottery to stylish clothing, you'll find it all here. Prices range from $15 to $3,000, ensuring there's something for every budget. And that's not all! Don't forget to check out the Green Market, featuring plants, orchids, exotic flora, handmade soaps, gourmet spices, and freshly popped kettle corn. Get ready to shop 'til you drop at this incredible craft festival!

11th Annual Oktoberfest at Edelweiss

October 11th-15th, Hours Vary | Edelweiss Restaurant

Get ready for the ultimate Oktoberfest experience at the 11th Annual Oktoberfest at Edelweiss in Bradenton! This exciting event features a large, open-air beer tent with seating, live entertainment including German music, fire spinners, and German dancers. Indulge in delicious Oktoberfest food, participate in contests and win amazing prizes, and of course, enjoy plenty of authentic German beer. The festivities kick off on Wednesday, October 11th with a keg tapping ceremony at 5 pm. There will be non-stop entertainment on stage under the beer tent. Best of all, admission is free! Make sure to mark your calendar and join in the fun at Edelweiss, located at 611 Manatee Ave E in Bradenton, FL.

Sarasota Rocktoberfest

October 13th-15th, Hours Vary | J.D. Hamel Park

Get ready to rock and roll at Sarasota Rocktoberfest! This exciting event will be taking place from October 13th to 15th, 2023 in J.D. Hamel Park. The best part? Admission to the festival is completely free! Indulge in delicious German cuisine such as Schweinshaxe, Steckerlfisch, Wurstl, Brezen, Knodel, Kasespatzel, sweet mustards, sauerkraut, and red cabbage. There will also be live performances and a marketplace featuring arts, crafts, and select fine products and services. And don't forget, the festival is pet-friendly! So mark your calendars and come out for a weekend of fun from Friday 4pm-10pm, Saturday 11am-10pm, and Sunday 11am-6pm.

8th Annual Sarasota Celtic Music Festival

October 13th-15th | Motorworks Brewing

The New World Celts - Sarasota Chapter is hosting Celtoberfest from October 13th-15th, and you definitely don't want to miss it! This event is a fusion of beer-swilling, kilt-sporting, lederhosen-loving merriment and live music. With vendors, food trucks, wine, cocktails, and craft beer, there's something for everyone to enjoy. The best part? It's family and dog-friendly! So grab your finest lederhosen, dirndl, or tartan and join in the festivities. It's bound to be a weekend of unforgettable fun at Celtoberfest in Sarasota!

Lights at Spooky Point

Starting October 13th, 6:30pm-9pm | Selby Gardens’ Historic Spanish Point Campus

Lights at Spooky Point is back for a second year and it's better than ever! This Halloween-themed light show is equal parts creepy, campy, and cute, making it perfect for the whole family. Tickets are $30 for adults ($20 for Selby Gardens members), $15 for ages 5-17, and free for children 4 and under. Early entry to Lights at Spooky Point is at 6:30 p.m. and general entry begins at 7:45 p.m. The last entry into Lights at Spooky Point is at 8:30 p.m. and the campus closes at 9 p.m., so make sure to plan your visit accordingly. Purchasing tickets in advance is strongly encouraged, so grab yours and get ready for a spooktacular evening!

Sharktoberfest

October 14th, 7pm-10pm | Mote Marine Aquarium

Sharktoberfest is the ultimate craft beer festival at Mote Marine Aquarium! Grab your friends and join in for a day of brews, bites, and marine fun. There's even a VIP Tasting Experience for $125 per ticket for those looking for a little extra. For $55 per ticket, you can enjoy admission to the main event, where you'll experience Mote Aquarium like never before. Live entertainment, food stations, merchandise vendors, and special experiences provided by Mote's Education department await you at Sharktoberfest. Plus, guests will receive a commemorative tasting glass and a branded gift bag to take home. Don't miss out on this unforgettable event!

32nd Annual Hunsader Farms Pumpkin Festival

Starting October 14th, 9am-5pm | Hunsader Farms

Get ready for the 32nd Annual Hunsader Farms Pumpkin Festival! Starting October 14th and every Saturday and Sunday for the rest of the month, you can enjoy a day filled with family-friendly activities. Live Music and Shows, Pumpkins, Kid's Pumpkin Games, Hayrides, Pony Rides, Corn Maze, Homemade Ice Cream, Farm Roasted Sweet Corn, Chainsaw Sculpting, Petting Zoo, Barnyard Playground, Train Rides, Fresh Produce, and even a Butterfly Experience are just a few of the highlights!

Admission is $15 and children 10 and under are free. Plus, dogs are welcome as long as they are friendly, on a leash, and you clean up after them. Don't miss out on this incredible event!

23rd Annual Morton's Firehouse Chili Cook-Off

October 15th, 2pm-5pm | Morton’s Gourmet Market

Get ready for a spicy showdown at the 23rd Annual Morton's Firehouse Chili Cook-Off! This fiery event will be held from 2pm-5pm on Osprey Avenue between Hyde Park Street and Hillview Avenue. Admission is free, but for just $10, you can sample all the mouthwatering chili varieties. Best of all, all the money raised will be donated to the Sarasota Fire Fighters Benevolent Fund. And the competition is fierce, with a panel of Celebrity Judges on hand to determine the ultimate chili champion. Don't miss out on this sizzling event!

22nd Annual Anna Maria Island Bay Fest

October 21st, 10am-9pm | Pine Avenue, Anna Maria Island

Get ready for a day of family fun at the 22nd Annual Anna Maria Island Bay Fest! You can browse through arts and crafts vendors, grab a bite to eat at the food court with food from local restaurants and vendors, and even enjoy a refreshing drink. This exciting event will also feature live music and a classic car show from 10am-3pm. Best of all, this event is family-friendly and admission is free. Don't miss out on all the excitement at the Anna Maria Island Bay Fest!

7th Annual Big Mama's Collard Greens Fest

October 21st, 12pm-6pm | Robert L. Taylor Community Park

Get ready to indulge in the mouthwatering flavors of the South at the 7th Annual Big Mama's Collard Greens Fest! This event celebrates the best-tasting family collard greens recipes, some dating back more than 100 years. At the collard green cook-off, local residents and restaurant chefs compete for the title of "Big Mama" and some fabulous prizes.

But it's not just about the competition. Attendees can also join in the tasting action and feast on soul food offerings from local chefs and vendors. It's a family-friendly, no-alcohol event, and make sure to bring your own lawn chairs or blankets for a comfortable and relaxing time. Don't miss out on this delicious celebration of collard greens and community!

Sarasota Water Lantern Festival

October 21st, 4:30pm-8:30pm | Nathan Benderson Park

Get ready for a magical evening at the Sarasota Water Lantern Festival! This family-friendly event at Nathan Benderson Park is an experience like no other. Each adult ticket includes a wristband for entry, a floating lantern kit, an LED candle, a commemorative drawstring bag, a marker, playing cards, and conversation cards. The ticket price also covers the cost of collecting and removing the lanterns from the water after the event. Food trucks, music, and fun will be happening from 4:30pm-8:30pm, with lantern design at 7pm and the lantern launch from 7:30pm-8:30pm. Don't miss out on this enchanting and uplifting event!

Halloween Trick-or-Treating at UTC

October 21st, 5:30pm-7:30pm | The Mall at UTC

Get ready for a spooktacular time at Halloween Trick-or-Treating at The Mall at UTC! Dress in your favorite costume and join in for mall-wide trick-or-treating fun. Make your way to the Grand Court and outside the main east entrance for exciting activities like character meet & greets, dance party, bounce houses, crafts, games, and more. Don't forget to bring your trick-or-treat bag, as candy will be available on a first-come basis. Be sure to arrive at the event start time to make the most of this Halloween extravaganza!

St. Armands Fall Festival of the Arts

October 21st-22nd, 10am-5pm | St. Armands Circle

Get ready for a weekend of artistic excellence at the St. Armands Fall Festival of the Arts on October 21-22, 2023! Held in the picturesque St. Armands Circle Park, this event showcases a stunning array of artwork from talented artisans. From vibrant paintings to intricate sculptures, dazzling jewelry to captivating photography, and so much more, there's something to captivate every art lover. With artists attending from across Florida and the United States, visitors have the unique opportunity to commission a one-of-a-kind piece. Best of all, this event is free! So bring your sense of discovery and immerse yourself in the beauty of the St. Armands Fall Festival of the Arts.

18th Annual Hungarian Festival

October 21st-22nd, Hours Vary | Sarasota County Fairgrounds

Get ready to immerse yourself in Hungarian culture at the 18th Annual Hungarian Festival! This lively event offers a wide range of activities for everyone to enjoy. From indulging in delicious Hungarian cuisine and pastries to trying your hand at traditional sports like archery and exploring arts and crafts vendors, there's something for everyone. Plus, live music, performances, and shows will keep you entertained all day long. Don't forget to visit the kids' corner for even more fun! Best of all, admission to the festival is free. Head to the Sarasota County Fairgrounds behind Robarts Arena off Fruitville Road on Saturday from 11am-10pm and Sunday from 12pm-8pm to join in the festivities!

3rd Annual Fall Festival at University Town Center

October 21st-22nd, 11am-6pm | University Town Center

Mark your calendars for the 3rd Annual Fall Festival! On October 21st and 22nd, come out to parking lot 4 (east side) at The Mall at UTC and enjoy a weekend of fall fun. There will be Carnival Rides, a Pumpkin Patch, Trunk or Treat (October 22nd from 4 - 6 pm), Community Performances, Food Trucks & Beer Truck, Fall-Themed Vendors, Photo Stops, Activities and more! Don't miss out on this exciting event that has something for everyone to enjoy. It's the perfect way to celebrate the season with family and friends. See you there!

Trick Or Treat On The Lake

October 26th, 5:30pm-8pm | Nathan Benderson Park

Get ready for a spooktacular evening of Halloween fun at Trick or Treat on the Lake! This family-friendly event is returning to Sarasota on Thursday, October 26th, and it's not to be missed. Join us at Nathan Benderson Park for a thrilling night of trick-or-treating along a candy trail, with themed booths decorated by community organizations. There will be interactive play, storytelling, and live music to keep the festivities going. So grab your costumes and come join us for an unforgettable evening of Halloween fun at Trick or Treat on the Lake!

7th Annual Legend of Sleepy Hollow & Fall Festival

October 26th-28th, 6pm | Sarasota Polo Club

Don't miss out on the 7th Annual Legend of Sleepy Hollow & Fall Festival at the Sarasota Polo Club! Immerse yourself in the haunting tale as you follow new schoolmaster Ichabod Crane through Sleepy Hollow. And that's not all - each night there will be a costume contest, so make sure to dress to impress! On October 28th from 3pm-6pm, join in the Fall Festival with food trucks, games, prizes, face painting, a photo booth, and a bounce house before the show!

Ticket prices are Adult-$25, Kid-$20 with a bracelet, Kids-$10 without a bracelet, and Family 4 pack– $75. Bracelets will be sold at the door for $15, so come prepared. Don't forget to bring your own blankets or chairs as this spine-chilling event is held outdoors.

BooFest

October 27th, 6pm-9pm | Lakewood Ranch Main Street

BooFest is back on Lakewood Ranch Main Street and it's bound to be a spooky good time! This free event features entertainment, food, and drink vendors, making it perfect for a fun-filled Halloween celebration. Don't forget to bring your trick-or-treat bags for the little ones, and be sure to dress up for the children's costume parade. Get ready to have a howling good time at BooFest!

20th Annual Boo Run

October 28th, 7:30am | Lakewood Ranch

Get ready to lace up your running shoes for the 20th Annual Boo Run! This exciting race is not only a fun way to get active, but it also supports two incredible charities: the Another Day for Gray Foundation and the Humane Society at Lakewood Ranch. And the fun doesn't stop there! Don't forget to dress up in your spookiest or silliest costume for a chance to win in one of the four categories: Best Pup/Human, Best Couple or Group, Best Adult, and Best Child. So join in on the Halloween festivities and run for a great cause at the 20th Annual Boo Run!

Trick or Treating at Bradenton Public Market

October 28th 9am-2pm | Old Main Street, Bradenton

Trick or treating at Bradenton Public Market is the perfect way to celebrate Halloween with the whole family! On October 31st, head to the market for a spooktacular time. From 9am to 2pm, market vendors will be handing out treats to little ghouls and goblins. Plus, there will be free face painting to add an extra touch of Halloween fun. Don't forget to come dressed up in your best costumes for a truly memorable and festive experience. It's a can't-miss event for Halloween lovers of all ages!

16th Annual Sarasota Dog-A-Ween Costume Contest

October 28th, 9am | Lemon Ave. & Whole Foods, Downtown Sarasota

Join in for a paw-some event at the 16th Annual Sarasota Dog-A-Ween Costume Contest on Saturday, October 28, 2023! This is a can't-miss event for dog lovers and costume enthusiasts alike. Special guests and judges, including ABC 7's Chief Meteorologist Bob Harrigon and Marsha Panuce, founder of Donte's Den Foundation, will be there to make the day extra special.

Registration is $15 on-site and check-in starts at 9:00 AM at Lemon Ave. & Whole Foods in downtown Sarasota. Watch the adorable parade of dressed-up pups as it makes its way through the Farmers Market to Paul Thorps Park. The contest kicks off at 10:15 AM. Plus, enjoy pet-friendly patios, delectable treats, and the scenic beauty of the bayfront. Join the movement and help make this event a howling success!

El Melvin Day of the Dead Block Party

October 28th, 4pm-2am | El Melvin Cocina Mexicana

Get ready to celebrate at the El Melvin Day of the Dead Block Party! This vibrant event is a feast for the senses, with delicious street food, live entertainment, and DJs provided by SRQ Beats. And don't forget the incredible fire-dancers that will be lighting up the night. Plus, there's a $1000 costume contest, so make sure to come dressed to impress! Get ready for a night of unforgettable surprises at the El Melvin Day of the Dead Block Party.

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Joyland Live's 27th Annual Boo Bash

October 28th, 9pm | Joyland Live

Get ready for a spooky night of Halloween fun at 27th Annual Boo Bash at Joyland Live! This year's event will feature the infamous Scareland Haunted House, guaranteed to send chills down your spine. But that's not all - there will also be a thrilling costume contest with $3,500 in prizes up for grabs. And of course, no Halloween party would be complete without giveaways, food and drink specials, and music with a live DJ. Doors open at 5:30pm and the party starts at 9pm, so make sure to mark your calendars and get your costumes ready. (There is a cover charge for this frightfully fun event.)

Gator Club's Annual Halloween Block Party

October 28th, 6pm | The Gator Club

Get ready for a night of spooktacular fun at the Annual Halloween Block Party at Gator Club! This year's event promises to be bigger and better than ever. Outside, enjoy live music from 22N on stage at 8:00pm and indulge in delicious treats from food trucks. Get ready to show off your dance moves and enter the costume contests for a chance to win amazing prizes. Inside, Johnny Diamond and DJ Kelly Crawford will keep the party going with live music all night long. With over $1500 in cash and prizes up for grabs, the costume contests are not to be missed. Plus, be prepared for surprise events throughout the night. It's going to be an unforgettable Halloween celebration!

Selby Gardens Spooktacular

October 29th, 10am-1pm | Selby Gardens

Get ready for a ghoulishly good time at Selby Gardens Spooktacular! This family-friendly, Halloween-inspired event is not to be missed. Join in on the fun with trick-or-treating, arts and crafts, and plenty of fun and educational activities for the whole family. For those brave souls, there are even more frightening options like an inflatable corn maze and spooky storytelling. Best of all, Selby Gardens Members get in for free. Don't miss out on this spooktacular event at Selby Gardens!

Siesta Key’s “Safe Treats” Trick-or-Treating

October 31st, 3pm-6pm | Siesta Key Village

Looking for a safe and fun way for your kids to trick-or-treat this Halloween? Look no further than Siesta Key's "Safe Treats" Trick-or-Treating event! Kids can enjoy trick-or-treating in Siesta Village along Ocean Blvd. and the surrounding streets. Participating merchants will have festive balloons to indicate that they are participating in the event. And the best part? The Siesta Breeze Trolley is offering free rides between the Village and Turtle Beach, making it convenient for families to get around. This free event provides a safe and enjoyable Halloween experience for the whole family. Don't miss out on the fun!

15th Annual Fright Night on St Armands Circle

October 31st, 6pm-8:30pm | St Armands Circle

Get ready for a spooktacular night of frightful fun at the 15th Annual Fright Night on St Armands Circle! This Halloween event is not to be missed. The store fronts will be adorned with eerie decorations, and frightening characters will roam the streets, ready to give you a scare. Both adults and children can participate in trick-or-treating throughout the Circle, as retailers and restaurants contribute to the Halloween spirit with candy, games, and customized promotions. It's the perfect event to get into the Halloween spirit and enjoy a night of spooky excitement!

Conclusion

With a wide variety of events and activities happening throughout the month, there's something for everyone to enjoy. From water ski shows to pumpkin festivals, craft fairs to block parties, the options are endless. So grab your friends and family, put on your favorite costume, and get ready for a month of unforgettable experiences. Don't miss out on the chance to create lasting memories and make the most of this exciting time in Sarasota.