Kissimmee Main Street

Kissimmee Main Street The Kissimmee Main Street program is a local 501(c)(3) organization dedicated to the preservation-ba
(2)

Sunday Night Wings & Bingo🍗 Good Wings. Great Times. BINGO! 🎉Grab some wings, play bingo, and enjoy a fun Sunday night w...
05/30/2026

Sunday Night Wings & Bingo

🍗 Good Wings. Great Times. BINGO! 🎉
Grab some wings, play bingo, and enjoy a fun Sunday night with friends.

📍1881 Restaurant and Bar
📅 Every Sunday
💲 $1 Wings

🤠 Thank you to everyone who joined us for the Great Kowboy Crawl!A special thank you to our volunteers, participating bu...
05/30/2026

🤠 Thank you to everyone who joined us for the Great Kowboy Crawl!

A special thank you to our volunteers, participating businesses, and celebrity bartenders who helped make the night such a success. We couldn’t do it without your support, energy, and community spirit.

Until next time, Kissimmee! 🍻⭐

Kissimmee Walk & Run ClubEvery Saturday. Every Face. Every Pace. 👟☕Join us at Kissimmee Lakefront Park for community, mo...
05/29/2026

Kissimmee Walk & Run Club

Every Saturday. Every Face. Every Pace. 👟☕
Join us at Kissimmee Lakefront Park for community, movement, and coffee! Walkers and runners of all levels welcome.

📍 Meet near Ruby Plaza Café
🕖 Meetup: 7:45 AM | Run/Walk Starts: 8:00 AM

DOWNTOWN DAD is coming to Historic Downtown Kissimmee! Celebrate Father’s Day the Main Street way with local vendors, d...
05/28/2026

DOWNTOWN DAD is coming to Historic Downtown Kissimmee!

Celebrate Father’s Day the Main Street way with local vendors, delicious food, family fun, unique gifts for Dad, and the Dad Cam Photo Booth by Memories in a Flash. 📸

We’re also proud to recognize Renaissance Charter School at Poinciana as a featured Market Sponsor for helping support local businesses and community events.

📅 Friday, June 5, 2026
⏰ 5PM–9PM
📍 Violets Garage
413 Broadway • Kissimmee, FL

Shop local. Support local. Support Dad.

05/28/2026

Tickets: https://www.zeffy.com/en-US/ticketing/kowboy-crawl--2026

🤠 TOMORROW WE CRAWL 🤠
Downtown Kissimmee is turning into Kowtown for one wild night of cocktail samplings, cowboy boots, and bar crawl fun 🍹🔥

🎟️ $25 Tickets
⏰ 6PM–9PM
📍 Downtown Kissimmee

Y’all ready or what?🤠

Vanguard Awards 2026✨ The Future Is Ours ✨Save the date for an inspiring evening celebrating leadership, excellence, and...
05/28/2026

Vanguard Awards 2026

✨ The Future Is Ours ✨

Save the date for an inspiring evening celebrating leadership, excellence, and community impact.

📅 June 18, 2026
🕕 6 PM – 10 PM
📍 Legacy Ballroom, Orlando

Five years of service, trust, and community!Join the Law Office of Mario Romero as they celebrate 5 incredible years of ...
05/28/2026

Five years of service, trust, and community!

Join the Law Office of Mario Romero as they celebrate 5 incredible years of serving Kissimmee and beyond. Through every challenge — even during COVID — your support and confidence made this milestone possible.

Enjoy an evening of appreciation, celebration, and connection under the white tent as we honor the clients, partners, and community who have been part of the journey. 🥂

📍 715 Mabbette St., Kissimmee, FL
📅 June 4, 2026
⏰ 5:30 PM

Kindly RSVP to Esmeralda Romero at (407) 640-4412 with your name and number of guests.

Here’s to five years of dedication — and many more to come. 🎉

Super Mario Skate Day⭐ It’s-a time to SKATE! ⭐Join us for a fun-filled Mario-themed skate session with a special Mario m...
05/27/2026

Super Mario Skate Day

⭐ It’s-a time to SKATE! ⭐
Join us for a fun-filled Mario-themed skate session with a special Mario meet & greet!

📅 Sunday, May 31
🕜 1:30 PM – 4:30 PM

👕 Wear a Super Mario costume & get a FREE slushy!

NAACP Osceola Branch – Day of Service💙 We Love Our Osceola Community 💛Join us for a day of service, family fun, food, mu...
05/27/2026

NAACP Osceola Branch – Day of Service

💙 We Love Our Osceola Community 💛

Join us for a day of service, family fun, food, music, games, and community connection!

📅 Saturday, May 30, 2026
🕛 12 PM – 4 PM
📍 Kissimmee Lakefront Park – Heron Pavilion

05/26/2026

This Friday!
https://www.zeffy.com/en-US/ticketing/kowboy-crawl--2026?fbclid=IwVERDUASC-FpleHRuA2FlbQIxMABzcnRjBmFwcF9pZAo2NjI4NTY4Mzc5AAEewnMhRbpLRxUtffNZlHpRSO84LKbQ7UDuLC22iFTeeqSgMLa3bAYFuWykkvs_aem_JEDLvUMzJPEm7OpG-g61Vg

Grab your crew, throw on the boots, and get ready for a wild night of drink samples, downtown games, and kowboy chaos from 6PM-9PM.

BUY ONE, GET ONE FREE tickets for a
limited time
Downtown Kissimmee
May 29th
6PM-9PM
$25
This ain’t our first rodeo... but it might be our rowdiest.

Expect:
Downtown bar crawl stops
Kowtown-themed fun
The Downtown Throwdown
Photo ops & cowboy-core vibes all
night

Address

421 Broadway
Kissimmee, FL
34741

Opening Hours

Monday 9am - 5pm
Tuesday 9am - 5pm
Wednesday 9am - 5pm
Thursday 9am - 5pm
Friday 9am - 5pm
Saturday 10am - 3pm

Telephone

+14078464643

Website

Alerts

Be the first to know and let us send you an email when Kissimmee Main Street posts news and promotions. Your email address will not be used for any other purpose, and you can unsubscribe at any time.

Contact The Organization

Send a message to Kissimmee Main Street:

Shortcuts

Share