Good morning, Kissimmee.

St. Cloud’s 17-year-old Bailee Jeannin became the first competitor to win all three Silver Spurs pageants when she was crowned Miss Silver Spurs in June 2024—she had won Little Miss Silver Spurs in 2017 and Junior Miss in 2021.

The Harmony High senior will serve as the rodeo ambassador and attend community events and other rodeos this year to promote the county’s rodeo tradition.

Congressman Darren Soto held a press conference on May 28—announcing over $33.5 million in FY25 Airport Infrastructure Grants for MCO and Kissimmee Gateway Airport—and representatives from the Greater Orlando Aviation Authority and Kissimmee Gateway Airport attended.

Residents in Orlo Vista are hopeful that a $23 million flood mitigation project will lower flooding risks during the upcoming hurricane season as temporary pumps replace the old system that failed during Hurricane Ian.

Longtime resident David Phillips said the county expects permanent pumps to be installed within weeks + the project comes after past floods from Hurricanes Irma and Ian.

Silver Spurs Rodeo

7:59-10:59 p.m. — Silver Spurs Arena — $15-$35 — Dust off your boots for an exciting rodeo showcasing cowboys and cowgirls competing for cash prizes.

Premiere Orlando Beauty Show

6 AM – 1 PM — Orange County Convention Center — Admission varies — Explore the latest innovations in the beauty industry at the largest beauty show in the U.S.

Island H2O Summer Kick-Off Event

10:30 a.m. - 6:00 p.m. — Island H2O Water Park — Parking $10, food additional — Splash into summer with over 20 fun water activities for all ages.

Mondays Suck Improv Show

7-9 p.m. — 1881 Restaurant & Bar — Entry fee may apply — Enjoy a hilariously spontaneous live improv comedy experience on a Monday night.

Island H2O Water Park: Fast Track Ticket

12 AM — Island H2O Water Park — Ticket prices vary — Dive into family fun with over 20 rides and attractions at this exciting water park.

Island Nights Summer Party

8 p.m. - 12 a.m. — Island H2O Water Park — Free entry — Celebrate summer with vibrant Island Nights featuring fun events every Saturday night.

2025 Florida State Finals

June 11-15 — Osceola Heritage Park — Registration fees apply — Experience the excitement of competitive barrel racing at the largest state finals event.

Rock & Brews Live Music Featuring Redline

8-11 p.m. — Rock & Brews — Free entry — Enjoy a night of live music with Redline at a local favorite venue.

Grow Osceola: 7 Deadly Sins of IT Security

9-11 a.m. — UCF Business Incubation Program - Kissimmee — Free entry — Discover critical IT security insights to safeguard your business with expert guidance.

Freestyle / Old School Brunch Party 2

1-6 p.m. — FUMA Lounge — Tickets required — Enjoy a lively brunch party with freestyle old school vibes and good company.