Annual Events in Kissimmee, FL

If you are planning to make a visit to Kissimmee, there are a variety of events that you should not miss. Kissimmee is considered as the “Gateway to Florida”, thus attracting thousands of visitors every year from all over the world. Kissimmee offers a wide range of local and international attractions that can surely fascinate your trip to Florida. It is home to the Florida International Auto Show, Kissimmee Tomato Festival, Osceola County Fair, and the Kissimmee Garden Center. There are also several Annual Events in Kissimmee to keep you and your family busy during your stay in the area.

Solar Company Kissimmee FL

The Kissimmee Tomato Festival held annually from mid-July to mid-September is one of the most popular fairs in the world. It brings together hundreds of growers and tomato breeders from throughout the U.S. This fair offers an assortment of live entertainment, top Tomato Sales, and exclusive product demonstrations and tastings. The festival is ideal for both the area’s new and seasoned tomato growers and consumers alike.


The Osceola County Fair happens in early May and is held at the Hyatt Regency Resort. This fair provides delicious food, arts and crafts, horse shows and specialty shows. Besides the fair itself, the Ocala National Forest offers numerous hiking trails, campgrounds, cabin rentals, camping, and nature programs. In the center of Osceola County, you will find the Osceola County War Memorial Park, which contains a museum, historical marker and picnic area.


The second Annual Kissimmee Garden Center Garden and Arts Festival happen in March and run for a week. This three-day extravaganza features musical performances by local and national artists, food and wine tastings, craft booths, and free live entertainment. This festival is ideal for kids and adults alike. The Osceola County Library Association hosts the fifth annual Garden and Arts Fest in the heart of Kissimmee.


For those who love country living, The International Garden Center in Greenville would be a perfect place to visit. It is one of the premiere garden centers in the state and is geared towards wholesome activities, education, and family fun. The center offers five indoor and two outdoor exhibits that feature a variety of seasonal flowers and plants. Also featured is a garden trail that leads visitors through the facility. There are educational exhibits, interactive exhibits, and storytelling experiences. This county-sponsored fair allows the community to experience “green living” in a hands-on manner.


Finally, consider the Suckers’ Festival, which occurs in May and is sponsored by The Suckers, local manufacturers of various promotional products including custom imprinted souvenirs. At this event, visitors can mingle at the vendors booths and buy unique souvenirs from the vendors. This is also a great opportunity to get to know local small businesses in the area. Another great feature of this festival is the free amusements. Music, wine and delicious food are featured throughout the day.




17 min
5.0 miles

via N Main St

Fastest route now due to traffic conditions

18 min
4.9 miles

via US-17 N/US-441 N/US-92 E and W Osceola Pkwy

Some traffic, as usual

19 min
4.8 mile