Events

KISSIMMEE MAIN STREET EVENTS

Trick or Treat on Broadway – October

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Little ghosts, goblins, witches and princesses  can come to Downtown Kissimmee for the annual Trick or Treat on Broadway event !  All costume kids receive a FREE bag to tote all their goodies in as they hop from shop to shop collecting only the best candy and treats from our downtown merchants ! We welcome patents to commemorate this event in the photo booth before heading our onto Broadway for some trick or treat fun. Then be prepared to dig into your candy bags as you head back to Toho Square for a FREE screening of a family friendly ghoul filled movie!

The Osceola Fall Art Festival – November

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On a 2-day long event amidst the beautiful backdrop of boutiques, antique shops and fine restaurants, guests will enjoy more than 100 artists and crafters at The Osceola Art Festival presented by Osceola Center for the Arts and Kissimmee Main Street.  Exhibits include oil painting, watercolors, sculptures, photography, graphics, and more. Plus food and musical entertainment make this an exciting event all taking place along Broadway Avenue.

 

The Festival of Lights Parade – December

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The City of Kissimmee and Kissimmee Main Street team up to present the Festival of Lights Parade in downtown Kissimmee. Strolling entertainers, holiday carolers, marching bands, seasonal food and beverages and an appearance by Santa! The parade lights up the Downtown Kissimmee streets with decorated floats from community organizations and businesses. Watch the lighted floats pass and see if you can spot the grand marshal and Santa. After the parade join us for the tree lighting ceremony of the downtown Kissimmee tree.

 

Kissimmee 5-K – February

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Kissimmee Main Street is proud to celebrate Valentine’s Day with the Annual KISS-IM-MEE 5k. This event promotes heart health with a portion of the proceeds benefiting the American Heart Association. Participants can enjoy a serene lake shore run as the early morning fog rolls over Lake Tohopekaliga. Runners will take in some of Kissimmee’s beautiful historic homes and find great shopping and dining venues as they run through historic downtown. Participants are certain to experience the best views of our charming and historic Downtown. This event is for runners of all abilities and walkers. Strollers are welcome.

 

Chili Cook-Off & Beer Festival – February

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Florida Beer Festivals has teamed up with the City of & Kissimmee Main Street to add a new Beer Festival dimension to one of Kissimmee’s great annual family fun events!

Sponsored by the International Chili Society, the Kissimmee Sunshine Regional CHILI COOK OFF & BEER FESTIVAL is a 3 category (Red, Verde, and Salsa) sanctioned chili cook-off. The ICS Red Chili winner will advance to the World Championship competition.

In addition to sampling some of the best homemade chili you’ll ever taste from up to countless chili cook teams, patrons will be able to purchase unlimited samples of great seasonal, craft, national & international brews. Admission is FREE! Bring the family and enjoy an afternoon of live music, arts, crafts and fun. Purchase tickets to sample delicious chili, cold brews and food. Saturday, February 21st at Kissimmee Lakefront Park starting at Noon.

 

The Kowtown Festival ft. The Kissimmee Valley Rib Rodeo – March

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A celebration in honor of The City of Kissimmee’s  Birthday at the Kissimmee Lakefront Park. With  live music, food, ice cold beer, the KUA Power Kids Zone, birthday cake and BBQ featuring  The Kissimmee Valley Rib Rodeo, a FBA sanctioned BBQ contest featuring the best BBQ in the southeast is an event not to miss! Fun for the whole family and admission and parking is always free.

 

Kissimmee Main Street’s Sculpture Pub Crawl – April

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The annual Kissimmee Main Street Sculpture Pub Crawl is a unique walking tour through Downtown Kissimmee featuring our Kissimmee Sculpture Experience, a series of sculptures placed throughout downtown, shops, restaurants, bars and galleries all while sippin’ on ice cold brew or good glass of wine! There is also a silent auction with lots of amazing items.

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