Kissimmee Main Street Kowboy Crawl — May 29

Get your cowboy hats, your boots and big ol' belt buckles to ride into a night of spirited fun as Kissimmee Main Street presents the Kowboy Crawl — a lively bar crawl experience across Downtown Kissimmee — on Friday, May 29, from 6-9 p.m.

This uniquely local event will feature multiple downtown bar stops, each offering 1-ounce drinks and cocktails served by Osceola “celebrity bartenders.” Along the way, participants will take on fun history-themed questions or mini-games at each location, combining a festive evening with a playful nod to Kissimmee’s roots.

Whether you're rounding up your friends for a night out or looking for an exciting way to explore the historic downtown scene, the Kowboy Crawl is your ticket to great drinks, great company, and a few surprises along the trail. Grab your boots and your sense of adventure – the Kowboy Crawl is here to serve up a little Kissimmee flavor, a splash of history, and a whole lot of fun! 

For sponsorship opportunities or to get involved — Wanna be a celebrity bartender? — contact info@kissimmeemainstreet.org.