Where Kissimmee goes out at night: Old Town's bars and car cruises, Sunset Walk's live music stages, downtown's wine and tapas bars and the rodeo.

Last checked Oct. 9, 2026. We list venues, not individual gigs; check each venue’s own calendar for who is playing. Sources: Old Town and its bar directory, the Promenade at Sunset Walk and its directory, Kissimmee Main Street, Vintage Vino, Silver Spurs Rodeo and the City of Kissimmee’s Festival of Lights.

Kissimmee’s nights out happen in three places: Old Town on U.S. 192, which says it is minutes from the theme parks; the Promenade at Sunset Walk; and the bars and restaurants on Broadway downtown. Here is each venue with its address and official link.

At a glance

  • Old Town: 5770 W. Irlo Bronson Memorial Highway, open to 11 p.m. Friday and Saturday, 407-396-4888
  • Promenade at Sunset Walk: live music calendar at sunsetwalk.com; free admission and parking
  • Downtown: Broadway bars and restaurants; Kissimmee Main Street, 407-846-4643
  • Getting home: plan a ride; see our getting around guide

Old Town

Old Town, 5770 W. Irlo Bronson Memorial Highway, is an entertainment district of bars, restaurants, shops and rides on brick streets. Its weekly lineup:

Night What
Wednesday Bike Night, 6 to 10 p.m., with live music
Thursday Karaoke
Friday Muscle Car Show and Cruise; cruise 8:30 p.m.
Saturday Classic Car Show and Cruise; cruise 8:30 p.m.

Bars in Old Town’s directory include Bobby’s Garage Bar, a 1930s and 1940s hot rod themed bar; Southern Breeze; Sun on the Beach; Olde Town Tavern; Maw’s Mountain Moonshine; and the frozen drink bars Fat Tuesday and Happy Daiquiri. Hamburger Mary’s, now open at Old Town, has bingo, trivia and shows. Old Town says some bars check ID for guests 21 and older. Hours: 11 a.m. to 9 p.m. Sunday to Thursday, 11 a.m. to 11 p.m. Friday and Saturday.

Promenade at Sunset Walk

The Promenade at Sunset Walk, by Margaritaville Resort Orlando, posts a monthly live music calendar of Central Florida acts playing rock, country, Latin, reggae and top 40 on the outdoor Promenade Plaza Stage and in its restaurants. Venues on that calendar include Mango Moon Bar and Grill at the Embassy Suites, 3151 Sunset Walk Drive, and the Margaritaville Resort Orlando lobby, 8000 Fins Up Circle.

Bars and restaurants in its directory include Rock and Brews, El Jefe Tequilas, The Wharf, Ford’s Garage, Fat Tuesday and Estefan Kitchen Orlando (open Tuesday to Sunday), plus Studio Movie Grill, GameTime and Escapology. Friday and Saturday nights add car and truck shows and an artisan market from 6 p.m. Admission and parking are free.

Downtown Kissimmee

  • Vintage Vino, 310 Broadway: a Tuscan-themed wine, cheese and specialty beer bar. Open 5 p.m. to midnight Wednesday, 5 to 10 p.m. Thursday and 5 p.m. to midnight Friday and Saturday. 917-627-8432.
  • Miguelo’s Ultra Lounge, 219 Broadway, and Soul Tapas and Bar, 24B Broadway, are listed in Kissimmee Main Street’s dining directory, with more bars and restaurants along Broadway.
  • Big John’s Rockin’ BBQ, 220 E. Monument Ave.: barbecue and a bar with music memorabilia, open until 9 p.m. Thursday to Saturday. 833-998-8701.
  • Jingle Bar Hop: Kissimmee Main Street’s holiday pub crawl downtown, 6 to 9 p.m., ages 21 and up. It was Dec. 12 in 2025; see our holiday lights page for 2026.

Big nights out

  • Silver Spurs Arena, Osceola Heritage Park, 1875 Silver Spur Lane: the Silver Spurs Rodeo in February and June and Monster Bulls on Feb. 13, 2027.
  • Old Town’s New Year’s Eve and Sunset Walk’s street party: see New Year’s Eve in Kissimmee.
  • Osceola Arts, 2411 E. Irlo Bronson Highway: the arts center has paused its Broadway Main Stage Series during renovations; check its site for what is on.

Getting home

Friday and Saturday nights bring Old Town’s car cruises at 8:30 p.m. and Sunset Walk’s car and truck shows. Plan your ride before you go. To report an impaired driver, call 911.

Related: date night in Kissimmee, downtown Kissimmee and things to do this month.

Frequently asked questions

Where is live music in Kissimmee?

The Promenade at Sunset Walk posts a live music calendar for its Promenade Plaza stage and restaurants, Old Town has weekly live entertainment and karaoke on Thursdays, and downtown bars on Broadway host their own nights.

What time does Old Town close?

Old Town lists its hours as 11 a.m. to 9 p.m. Sunday through Thursday and 11 a.m. to 11 p.m. Friday and Saturday. Some bars check ID for guests 21 and older.

Is there a wine bar in downtown Kissimmee?

Yes. Vintage Vino, a wine, cheese and specialty beer bar, is at 310 Broadway and opens at 5 p.m. Wednesday through Saturday.