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The Biggest Festivals in Southwest Florida

There’s a lot to celebrate in southwest Florida. If you want to join in on the celebrating, be sure to participate in some of the exciting events and festivals. Find out all about the biggest festivals in southwest Florida and mark your calendar.

Swamp Cabbage Festival

Although southwest Florida is renowned for its beaches, there’s much more to the region than the coastline. As soon as you head inland, you come across farmland and a different way of life. You’ll also come across swamp cabbage, or hearts of palm. At the Swamp Cabbage Festival, celebrate the unique delicacy and explore a different culture.

The festival takes place in LaBelle, where it has been going strong for over 22 years. It was started as a way to honor swamp cabbage, which comes from the sabal palm. But it also displays the folksy atmosphere of LaBelle. Generally, the event draws over 30,000 people to the town.

While at the festival, you can watch a beauty pageant, listen to the high school band, and watch a rodeo. If you view the rodeo, you’ll get to see the local cowboys in action. It’s entertaining for the whole family.

One of the more interesting events is the armadillo race. They might not be fast, but they are fun to watch. A festival highlight is the parade, where you can watch locals show off their town pride.

Island Hopper Songwriter Fest

For ten days, the Island Hopper Songwriter Fest brings top musical talent to Southwest Florida. Each year, the event moves around some of the most popular destinations in the region. Captiva, Fort Myers, and Fort Myers Beach are all festival venues for a few days.

The event attracts singer-songwriters from all across the country. Because of its strong musical scene, Nashville is always represented. Over 80 artists attend the festival and there are over 100 shows. The live performances take place in smaller venues, giving audiences an up-close and personal experience. 

Shark’s Tooth Festival

Venice is considered to be the shark’s tooth capital of the world. After a short walk on the beach, you’ll discover why. You’re likely to come across one or more shark teeth as you stroll the sandy shoreline. 

In celebration of the shark teeth, the city hosts an annual festival. Fossil collectors from across the state gather to show off and sell their shark’s teeth and other fossils. You never know what unique fossils you may come across. 

In addition to viewing fossils, you can also check out artwork. Over 100 artists demonstrate their talent. As you walk around, you can listen to live entertainment and eat food made by local restaurants and food trucks.

The proceeds from the Shark’s Tooth Festival support the Sarasota branch of the Special Olympics Florida. 

Naples Pride

Although Naples, Florida isn’t known as a popular LGBTQ destination, it hosts an annual pride event that deserves a mention. For several years, Naples Pride has been taking place in the beautiful Cambier Park. It brings together the LGBTQ community and celebrates the diversity of all of Southwest Florida. In fact, the event draws in people from all over the state. 

A family-friendly event, Naples Pride features celebrity speakers, musicians, and entertainers. The drag performances are particularly memorable and are a great introduction into LGBTQ culture. When there are no live performances, a DJ keeps the party going. For the duration of the event, there are kids activities, food vendors, and exhibitors. 

Every year, about 5,000 people attend the festival. There’s an optional entry fee that goes towards a charitable contribution. It’s one of the biggest festivals in Southwest Florida to celebrate the LGBTQ community.

Fort Myers Seafood & Music Festival

A relatively new festival, the Fort Myers Seafood and Music Festival shouldn’t be overlooked. 2020 marked the festival’s third year, but the popularity of the event makes it seem as if it’s been going on for decades.

This festival takes place along the waterfront in historic downtown Fort Myers. It highlights some delicious seafood, but also has other meat and vegetarian options. Southwest Florida’s greatest cooks come together to serve up dishes that satisfy everyone. When you order a seafood dish, you’re getting seafood that’s caught directly in Florida. You can wash down your meal with an alcoholic or non-alcoholic beverage.

As you enjoy the food, you can listen to music performed by Florida’s top musicians. There’s something for everyone – rock, jazz, reggae, and R&B music is featured every year. In 2020, the Billy Rice Band, Dr. Dave Band, and a Fleetwood Mac tribute band performed. When you’re not eating or listening to music, you can check out the arts and crafts sold by various vendors. 

Everglades City Seafood Festival

Everglades City is a little gem hidden south of Naples. Although the area doesn’t attract many tourists during the course of the year, there’s one exception. When the Seafood Festival comes around, people travel from all over the state to attend.

This festival has been going strong since 1970. As a charitable event, all of the proceeds go back to the community. 

If you attend, you’ll be treated to extremely fresh seafood. Most of the fish and shellfish are caught locally and the chefs know exactly how to make each dish a showstopper. There are also craft booths featuring local artwork and products. While the shirts shop, kids can enjoy the carnival rides.

Cape Coral Arts and Music Festival

Once a year, Cape Coral is home to a massive arts and Music Festival. The Cape Coral Arts and Music Festival occurs on the streets of downtown Cape Coral and brings life to the growing city. Since 1985, it’s been showcasing the area’s incredible artistic talent.

The festival features over 300 artists, many of whom are local. It’s the first and largest juried art fair in all of Lee County.To make things even more exciting, there’s live music. Stop by some of the city’s great restaurants and shops. While you’re there, you can pick up some interesting souvenirs. 

Attending the Biggest Festivals in Southwest Florida

Whatever your interests may be, there’s a festival in Southwest Florida that will pique your interests. Pull out your calendar and start planning your next festival.


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