7:00 pm
Cavetown - Running With Scissors Tour
House of Blues OrlandoOrlando, 32830 16 mi away
Live Music
Around Kissimmee
1313 events within 25 miles of Kissimmee · page 3 of 4
7:00 pm
Rollins College Women's Soccer vs Eckerd College - Senior Night
CampusWinter Park, 32789 21 mi away
School
7:30 pm
Orlando City SC v DC United - Pride in Our City
Inter.co StadiumOrlando, 32805 16 mi away
Festivals & Fairs
1:00 pm
UCF Knights Volleyball vs. West Virginia University Volleyball
THE VENUE AT UCFOrlando, 32816 16 mi away
Sports & Active
4:00 pm
Healthy Kids Running Series Fall 2026 - Lake Nona, FL
Lake Nona High SchoolOrlando, 32832 16 mi away
Sports & Active
5:00 pm
Orlando Solar Bears vs. Florida Everblades - Opening Night
Kia CenterOrlando, 32801 16 mi away
8:00 pm
CHRMNG, with Jeanwilder, White Star, and Tet Spells
Will's PubOrlando, 32803 16 mi away
Festivals & Fairs
7:00 pm
FREE Horror Trivia (Halloween Horror Nights Edition)
ConduitWinter Park, 32792 21 mi away
Holiday
7:30 pm
Buena Vista Social Club (Touring) - Recommended for Ages 8 and Over
Dr. Phillips Performing Arts CenterOrlando, 32801 16 mi away
5 more dates through 25 Oct
12:30 pm
Adult Movie Matinee (Ages 18 and older)
Community Center - 3101 17th Street St Cloud FlSt. Cloud, 34769 9 mi away
1 more date through 18 Nov
6:00 pm
Rollins College Men's Soccer vs Florida Tech
CampusWinter Park, 32789 21 mi away
Sports & Active
7:00 pm
Lilyisthatyou "The Flowers Have Feelings" Tour in Orlando
The AbbeyOrlando, 32801 16 mi away
5:00 am
2026 Disney Wine & Dine Half Marathon Weekend with A Running Passion
WALT DISNEY WORLD ResortOrlando, 32830 16 mi away
Sports & Active
1:00 pm
Navigating the Aging Body Series: How You Talk to Yourself About Yourself
Orlando Museum of ArtOrlando, 32803 16 mi away
Arts & Theater
7:00 pm
UCF Knights Womens Soccer vs. Cincinnati Bearcats Women's Soccer
UCF Soccer and Track ComplexOrlando, 32816 16 mi away
Sports & Active
7:00 pm
Jeff Arcuri: Fresh Cut (21+ Event)
Funny Bone Comedy Club - OrlandoOrlando, 32819 16 mi away
2 more dates through 24 Oct
7:00 pm
Sorry Ghost - The Insufferably Indie Tour with Special Guests
Stardust Video & CoffeeOrlando, 32803 16 mi away
7:00 pm
Haunted Illusions Starring David Caserta
Garden Theatre on Plant - 160 W. Plant StreetWinter Garden, 34787 21 mi away
7:00 pm
The Number Twelve Looks Like You, Kaonashi, and Differences
ConduitWinter Park, 32792 21 mi away
Rollins College Women's Tennis vs Rollins College
CampusWinter Park, 32789 21 mi away
Sports & Active
Rollins College Men's Tennis vs EFSC/Southeastern/New College of FL
CampusWinter Park, 32789 21 mi away
Sports & Active
4:30 am
2026 Disney Wine & Dine Half Marathon Weekend
Walt Disney World ResortOrlando, 32830 16 mi away
Sports & Active
10:00 am
Halloween Spooktacular Preschool Program
Jessie Brock Community Center - 310 N. Dillard StreetWinter Garden, 34787 21 mi away
Holiday
10:00 am
Grand Opening/Ribbon Cutting Ceremony: Tucker Ranch Holistic Health & Wellness Park and Botanical Garden
100 Avalon RoadWinter Garden, 34787 21 mi away
Business & Networking
7:00 pm
FLAGMAN with Special Guests The Dark Arctic, Pinkish, and Hutch
Will's PubOrlando, 32803 16 mi away
7:00 pm
Rollins College Women's Volleyball vs Florida Southern - Dig Pink
CampusWinter Park, 32789 21 mi away
Sports & Active
UCF Knights Football vs BYU - Homecoming
Acrisure Bounce HouseOrlando, 32816 16 mi away
Sports & Active
Rollins College Sailing vs Lake Virginia Invitational
CampusWinter Park, 32789 21 mi away
Sports & Active
1:30 am
Lecture: The Three Marjorie(y)s and How They Changed Florida
Orlando Museum of ArtOrlando, 32803 16 mi away
Classes & Clubs
10:00 am
National Prescription Drug Take Back Day
Winter Garden Police Department 251 W. Plant StreetWinter Garden, 34787 21 mi away
11:00 am
Rollins College Women's Swimming vs Nova Southeastern
CampusWinter Park, 32789 21 mi away
Sports & Active
1:00 pm
Rollins College Softball vs Seminole State
CampusWinter Park, 32789 21 mi away
Sports & Active · +1 more time this day
4:00 pm
Rollins College Women's Volleyball vs Tampa
CampusWinter Park, 32789 21 mi away
Sports & Active
5:30 pm
Maitland Fall-o-Ween Festival
1776 Independence LaneMaitland, 32751 22 mi away
Festivals & Fairs
7:00 pm
Orlando Solar Bears vs. South Carolina Stingrays
Kia CenterOrlando, 32801 16 mi away
1 more date through 23 Nov
7:30 pm
Orlando City SC v NYCFC - Military Appreciation Night, pres. by Audi
Inter.co StadiumOrlando, 32805 16 mi away
7:00 am
IACP Police Chase 5K at SeaWorld Orlando
7007 Sea Harbor DriveOrlando, 32821 16 mi away
Sports & Active
1:00 pm
UCF Knights Womens Soccer vs. University of Houston Cougars Women's Soccer
UCF Soccer and Track ComplexOrlando, 32816 16 mi away
Sports & Active
5:00 pm
UCF Knights Mens Soccer vs. Univ of South Carolina Gamecocks Mens Soccer
UCF Soccer and Track ComplexOrlando, 32816 16 mi away
Sports & Active
5:00 pm
Night of the Beast: An Evening Horror and Vintage Market
ConduitWinter Park, 32792 21 mi away
Markets & Pop-ups
7:00 pm
Coraline’s Collapse (‘Don’t Look Down’ Album Release Show) with Playing With Knives, MUNGE, What We Seek, and Deresonate
Will's PubOrlando, 32803 16 mi away
6:00 pm
Rollins College Women's Basketball vs Santa Fe College
CampusWinter Park, 32789 21 mi away
Sports & Active
7:00 pm
Year Of The Knife with St. Clovis, Retina, Self Inflicted Wound, and Coldest Blood
Will's PubOrlando, 32803 16 mi away
7:00 pm
Rollins College Women's Volleyball vs Palm Beach Atlantic
CampusWinter Park, 32789 21 mi away
Sports & Active
11:00 am
Adult Lunch & Learn (Ages 18+)
Marina Banquet Hall - 1104 Lakeshore Blvd. St Cloud FlSt. Cloud, 34769 9 mi away
9:00 pm
Inferno: A Hell Themed Halloween Party (Void. Terror. Silence - Halloween Edition)
ConduitWinter Park, 32792 21 mi away
Holiday
10:30 am
Toddler Boo Bash
Civic Center - 3001 17th Street St Cloud FlSt. Cloud, 34769 9 mi away
Kids & Family
6:00 pm
Rollins College Men's Soccer vs Saint Leo University - Senior Day
CampusWinter Park, 32789 21 mi away
Sports & Active
7:00 pm
UCF Knights Mens Soccer vs. Georgia State Panthers Men's Soccer
UCF Soccer and Track ComplexOrlando, 32816 16 mi away
Sports & Active