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October Things To Do In our City!

The fall weather is creeping in for us Floridians! As we shift into the new season, it's a perfect time to plan out things to do with your family, friends and self! We've gathered a list of some things to put on your "to do" list in your city for October!

Winter Garden / West Orange

National Night Out Community Event (October 4) Join the Winter Garden Police Department for a Night Out Against Crime at the annually-celebrated National Night Out. The event includes free food, children’s activities, meet and greet with your local police officers, demonstrations, crime prevention tips, and fun for all ages!

Halloween Experience 2022 (October 21–31) Halloween is celebrated for 11 days – not just one -- in Winter Garden! The City’s Halloween Experience provides family-friendly festivities in Downtown Winter Garden, including seven nights of an outdoor animated Halloween Light Show on City Hall; a hay maze; fall- and spooky-themed photo locations, decorations and light displays throughout downtown; a Spooky Caboose; a Halloween Celebration at the fall-themed Farmers Market; a Downtown Harvest Sidewalk Sale & Stroll; and more! Costumes are welcome any day!

Harvest Sidewalk Sale & Stroll (October 22) All Day - Shop the outdoor sidewalk sale surrounded by the spooky and fall-themed Halloween Experience ambiance. Stores will feature special sales, promotions, and seasonal merchandise.

Crooked Can Annual Oktoberfest: October 14 4:00 PM -October 16, 6:00 PM Winter Garden’s Crooked Can Brewing Company is loads of fun at any time. For one October weekend, it will up the festivity factor yet more. The 8th Annual Crooked Can Brewing Company Oktoberfest will span three days. In addition to the brewery’s suds, you’ll have access to German-inspired foods, live music (yes, dancing too) and Wiener Dog Races. That music? It’ll be by bands with names like Apple Strudel Oktoberfest Band and The Brussel Sprouts German Polka Band. Ya gotta smile, right? The whole shebang is family-friendly. Crooked Can is inside Plant Street Market, so other goodies will be available too

Halloween Spooky Sprint 5K October 30th

Hamlin Town Center. This isn’t a trick - it’s the best Halloween themed run around! Treat yourself and the whole family to this themed fun run in Hamlin/Winter Garden.

Clermont Harvest Festival October 29 2022

Head over to Historic Downtown Clermont for a good old fashioned family harvest festival full of fun and festive spirit.

There will be a pumpkin patch and photos plus a kidzone, offering train rides, rock climbing, wall bounce house, face painting and a costume contest.

There will be over 175 vendors showcasing homemade and handmade goods, one of a kind collectables and gifts.

Food trucks will be available for snacks and the Downtown restaurants will all be open. And decorated! Where: 685 W. Montrose St Clermont. Web: Clermont Downtown Partnership


Fairy Doors at Leu Gardens October 1-31 2022

Orlando in October is a magical time for many reasons. Fairies are hiding behind their adorable fairy doors until October 31st 2022. There are 20 unique and whimsical fairy doors to discover throughout the 50 acre gardens. A map showing the locations of all Fairy Doors is available.

Orlando in October: Come Out With Pride Festival

October 15 2022

Orlando in October is home to Come Out with Pride Festival. The event attracts over 150,000 visitors with a massive parade lining the streets of downtown Orlando.

There’s a marketplace filled with vendors from and supporting the LGBTQ+ community as well as the most impressive entertainment and fireworks display.


October 21-23 2022

Covering 10 city blocks, IMMERSE is an explosion of music, dance, acrobats, murals, projection experiences, theater, and interactive installations.

Organized by the Creative City Project, over 1,000 artists and performers take you into a world of creativity and adventure.


Oct. 29: Not your ordinary race, the Creepy Crawl has a costume contest for humans and pets, trick or treating, food, music and prizes. Benefits the Hemophilia Foundation of Greater Florida. Harbor Park at Baldwin Park, 4990 New Broad St., Orlando. 800-293-6527 or 407-629-0000.


Oct. 29: Celebrate the scary and enjoy creepy crafts and candy. 10 a.m.-3 p.m. Orange County Regional History Center, 65 E.

Central Blvd., Orlando. 407-836-8500.

Winter Park

Winter Park Autumn Art Festival

October 8-9 2022

Orlando in October brings us this fan favorite art extravaganza. The organizers expect more than 40,000 visitors for this annual event where local artists display their exceptional wares.

Food is supplied by local restaurants and live entertainment keeps adults happy. Workshops for children will keep them occupied and, hopefully, educated.

When: Saturday October 8 and Sunday October 9 2022 – 9am-5pm Where: Central Park, Winter Park, FL 32789

Popcorn Flicks in the Park October 13 8:00pm - 10:00pm

Movie Title - The Addams Family

(Presented by Winter Park's CRA, in partnership with Enzian Theatre and sponsored by AdventHealth)

This film series features classic films for the whole family. We encourage you to bring a blanket, a picnic or snacks, and some family and friends.

Trick or Treating at the Market October 29 8:00am - 1:00pm

Come Shop, Come Eat, Come tirck or Treat! Enjoy a morning in the sun while trick or treating to all the market vendors who will have lots of treats!

Don't forget your costumes! Winter Park Farmers' Market

Halloween Trunk Fest October 31 6:00pm - 8:30pm

This is a FREE event for all ages.

Enjoy an evening with family and friends trunk or treating! Local businesses and organizations will decorate their vehicles and pass out candy to trick-or-treaters. This event is located in the parking lot of the Winter Park Community Center

Oviedo/Winter Springs


Through Nov. 4: Meet the friendly folks at the slaughterhouse, including Butcher Dave; Ghostly Heff, who enjoys killing via deadly gas; and Gina and Girdy, twin turkeys with a taste for human flesh. Buy tickets online. 15239 Lake Pickett Road, Orlando.

Winter Springs Festival Of The Arts OCTOBER 15 & 16 10:00 AM - 5:00 PM

TUSCAWILLA & BLUMBERG BLVD. 1160 TUSCAWILLA RD. WINTER SPRINGS, FL 32708 The Oviedo-Winter Springs Regional Chamber of Commerce and the City of Winter Springs proudly produce and host the Winter Springs Festival of the Arts (WSFOTA) on beautiful Blumberg Blvd. in the Winter Springs Town Center. This is an opportunity to enjoy award-winning art, meet the artists, savor delicious food & craft beers, enjoy rockin' entertainment, and let your kids explore their artistic talents in the kid’s crafts area!

Halloween Craft at Green Acres Farm Oviedo Sun, Oct 16, 9 AM – 12 PM

HOME TOWN HARVEST Saturday October 29, 2022

4:30 p.m. - 8:30 p.m. Central Winds Park

Celebrate Fall at the 16th annual Hometown Harvest presented by Orlando Health! From FREE hayrides to live musical performances, this event hosts a large collection of fun activities. Various vendors will be available with food, drink, and other goods. Kids can enjoy bounce houses and pumpkin painting.

Mall-O-Ween Trick or Treat October 31st 4-6pm

Explore the mall and enjoy your favorite stores while collecting goodies and treats!

Osceola / Polk County

1. Halloween Lights at Jeater Bend

October 15-31 2022

The Lights at Jeater Bend is a street wide display of Halloween themed lights and music. It’s great fun for all the family. The display features a wide range of Halloween and Disney themed displays. Park up on the main road and stroll along Jeater Bend to see it all.

When: Nightly from 7pm, October 15th to 31st 2022 Where: Jeater Bend, Celebration, Florida

Oktoberfest at Krush Brau Park

Krush Brau Park (KBP) is once again holding Oktoberfest from September 16th to October 30th. The event features all of the best and well-known German beers, food, and gifts. Also featured are some of Central Florida’s breweries Oktoberfest beers.

there will also be a keg tapping ceremony plus several other contests including bier stein holding, yodeling, German limbo, German Schuplattler dance, best dressed Oktoberfest person and much more.

General admission is $5, children under 12 free, Veterans free. VIP tickets are also available.

When: September 16th – October 30th 2022 – Thursdays (October only) 4pm-11pm, Fridays 4pm-11pm, Saturdays/Sundays 12pm-11pm Where: Krush Brau Park, 4580 W Irlo Bronson Memorial Highway, Kissimmee, FL 34746 Web: Krush Brau Park

Lego o Land Select Dates October 1-31 2022

A perfect Trick or Treat for the younger kids with Brick or Treat at LegoLand.

Lots of activities including LEGO ghost building, Scavenger Hunt, Costume Contest, Meet & Greet with LEGO characters, a 13 foot Vampyer Hearse and a fireworks finale. All included with the entry ticket. Where: LEGOLand Florida, Legoland Way, Winter Haven, FL Web: Legoland Florida

Celebration Florida Oktoberfest October 21-22 2022

Orlando in October doesn’t bring the cooler weather usually associated with fall, but that doesn’t stop us cozying up in Central Florida! Just like we have Now Snowing at Christmas, the Town of Celebration also treats us to Falling Leaves during Oktoberfest.

Leaves fall 3 times a night at 7pm, 8pm and 9pm along Market Street.

Enjoy a traditional German experience featuring live music. Join in the interactive live show featuring everything from yodeling to crowd sing-a-long fun.

This is a family event with hayrides, pumpkins and fun. Check out our Celebration Dining Guide if you’re looking for a bite to eat.

Where: Celebration Town Center Web: Oktoberfest at Celebration

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