Kissimmee Events and Festivals

(Kissimmee, Florida - FL, USA)

Kissimmee's calendar of events and festivals is a somewhat sedate affair and visitors to the city should consider driving the short distance to Orlando, which offers a much wider and varied set of annual spectacles.

However, Kissimmee is famous for it Bluegrass Festival in March and its JazzFest event in April, both of which draw visitors in their thousands from places in-state, out-of-state and beyond. Also, Disney's Wide World of Sports, on Victory Way in Kissimmee, is a leading sporting complex, regular hosting major American football matches and many other large sporting events. Below is a list of the most popular annual events, seasonal things to do and lively festivals in the Kissimmee and Orlando area.

National Public Holidays

  • 1st January - New Year's Day
  • Third Monday in January - Martin Luther King Day
  • 12th February - Lincoln's Birthday
  • Third Monday in February - Washington's Birthday
  • Last Monday in May - Memorial Day
  • 4th July - Independence Day
  • First Monday in September - Labor Day
  • Second Monday in October - Columbus Day
  • 11th November - Veterans Day
  • 4th Thursday in November - Thanksgiving
  • 25th December - Christmas Day

Calendar of Festivals and Events 2014 / 2015


  • Kissimmee St. Cloud Senior Games - late January, the Kissimmee St. Cloud Senior Games is an annual event that sees a range of venues in Osceola County hosting a variety of games aimed at over 50s. Winners of heats have a chance to compete in State Senior Games later in the year.


  • Osceola County Fair and Livestock Show - early February, every year the Osceola Heritage Park plays host to the ten-day Osceola County Fair and Livestock Show, which sees all manner of agricultural and carnival-related events. Expect big crowds at this popular event, especially when the rodeo event commences.


  • Kissimmee Bluegrass Festival - early March, the Kissimmee Bluegrass Festival is an event lasting four days and featuring a variety of bluegrass gospel music performances as well as Southern food stalls and arts and crafts booths.


  • JazzFest Kissimmee Festival - this annual event is a must for lovers of the jazz scene. Visitors are treated to a variety of performances by both amateur and professional musicians. Food and drink are also available.


  • Orlando International Fringe Festival - head the short distance to Orlando and experience the annual 10-day International Fringe Festival, which sees a wide selection of theatrical and performing artists take to the streets, local converted office spaces and theaters to offer visitors the best in alternative entertainment .


  • International Orchid Fair - this annual event held at Kissimmee's World of Orchids is a chance for visitors to witness orchid growers from all over the world unite to showcase some of the most magnificent orchids the planet has to offer.


  • Independence Day Celebrations - July 4th, one of Osceola County's biggest annual events, the July 4th celebrations see a host of interests including a food festival, arts and crafts, karaoke, stage entertainment, water ski show and the customary fireworks spectacular.


  • The 'Pins Around Our World' Festival - mid-August, lovers of pin badges should head for Orlando in order to attend this annual event at which they are given the opportunity to view and purchase rare and unusual Disney pins from other collectors. During the four-day event, Disney releases twenty new limited edition pins that visitors have the chance to bid for.


  • Annual Mexican Fiesta - held at Orlando Festival Park, the Annual Mexican Fiesta is a commemoration of Mexican Independence Day and offer visitors stalls and displays featuring traditional Mexican food, art, folklore and music.


  • Epcot's International Food and Wine Festival - mid-October to mid-November, take a short drive to Epcot in Orlando for a festival that celebrates the culinary delights of more than 30 nations. Close to Kissimmee, visitors can treat their taste buds to samples of some of the world's most exquisite edible products at more than 20 international food and wine displays.


  • The Osceola Art Festival - mid to late November, the Osceola Art Festival is an annual event held at Lakefront Park that offers visitors the chance to view some of the country's most inspiring works of art. Pieces on display include sculpture, photography and oil paintings among other genres.


  • Annual Christmas Parade - Kissimmee sees in the Yuletide season with its annual parade, featuring brightly lit floats that make their way across the city. Festive music, food and drink can be found everywhere along the parade's route.