Guide to Labor Day Weekend in Tampa: Festivals, Events, Things to Do

Clearwater Beach, Florida
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Labor Day weekend in Florida is still considered to be low-season for tourists since the humidity can be stifling and rain is a near-daily occurrence. On top of that, it's also the peak season for hurricanes in the area, but if you don't mind the weather, then the smaller crowds and hotel deals should be enough to entice any traveler to visit Tampa for the holiday weekend.

A full slate of events during Labor Day can keep everyone entertained, from families with kids to college friends to retirees. Whether you're looking for a beach party or an art show, plus everything in between, Tampa has something for everyone to enjoy on Labor Day weekend.

01 of 09

Party at Caddy's on the Beach

About 40 minutes from downtown Tampa, you can enjoy Labor Day festivities on one of Florida's most picturesque and wildest beaches—Sunset Beach on Treasure Island. Caddy's is a chain of bars throughout Florida known for raucous beach parties, and the Treasure Island location is the original and flagship restaurant. You can rent a private cabana or beach chairs right on the sand for free to enjoy the entire day by the water, as long as you spend a minimum amount on drinks and food.

Caddy's typically has a line-up of events planned throughout the summer, including Labor Day, such as live music, movie nights, yoga classes, and drinking games. However, the event calendar has been put on hold for 2020. But the beach and Caddy's are both open, so you can still enjoy the long weekend near the water with unbeatable views of the Gulf of Mexico.

02 of 09

Bowling Marathon at Pin Chasers

Bowling fanatics can enjoy a full-day bowling extravaganza at Pin Chasers on Labor Day at their annual Bowling Marathon. Beginning at 9 a.m., competitors begin bowling and continue on for 12 hours to see who can complete the highest number of games in that time. Players are allowed to stop for no more than five minutes at a time for quick breaks to get food or use the bathroom, but other than that, it's non-stop bowling.

Pin Chasers has three locations throughout the Tampa area: one in Midtown, one near the airport, and another just outside of the city in Zephyrhills. Only a limited number of bowlers are allowed to compete in this popular Tampa tradition, so check the official event webpage for information about how to register.

03 of 09

Electronic Music at Shephard's Beach Resort

The Live Beach House Labor Day event at Shephard's Beach Resort is canceled in 2020.

Labor Day weekend marks "Live Beach House" at Shephard's Beach Resort on Clearwater Beach with live electronic international DJs, drink specials, and plenty of fun on the private beaches of the Gulf of Mexico.

Whether you are up for a champagne brunch or a tropical pool deck with cabanas, those 21 and above and willing to follow the required dress code are sure to have a good time.

04 of 09

Celebrate at MacDinton's Irish Pub

Labor Day events at MacDinton's are not scheduled to take place in 2020. Check the pub's official webpage and Facebook for the most up-to-date information.

The party at MacDinton's Irish Pub and Restaurant in SoHo (South Howard Avenue) in Tampa's Hyde Park neighborhood starts on Sunday and lasts until Monday night. With kiddie pools, frozen drinks, and barbecue on the menu, this Irish bar with a friendly vibe is a perfect place to celebrate more than just St. Patrick's Day. They also have an annual Pre-Labor Day Bash with drink specials.

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05 of 09


GeckoFest is canceled in 2020.

GeckoFest is an annual family-friendly event in the artistic community of Gulfport, about 40 minutes outside of Tampa. The festival doesn't involve real geckos, but it is a huge weekend celebration with outdoor concerts, art shows, local crafters, activities for kids, a "Gecko Ball" dance party, and more. The focus of the festival is on local artists who are able to showcase and sell their goods.

The festival takes place each year during Labor Day weekend, located along Beach and Shore boulevards in this waterfront village. Admission to the festival and parking are both free.

06 of 09

Stroll or Picnic at a Tampa Park

If you are seeking some exercise and outdoor recreation for the holiday weekend, one option is to visit one of Tampa's many parks. Al Lopez Park has a fitness trail offering exercise suggestions and you can catch some shade and picnic tables as you walk around the lake. Rowlett Park is a riverfront area, home to the first wheelchair softball field in Florida. For swimming, go to the pool at Copeland Park. Art and lovers of all things past should check out the sculptures and historic photographs at Perry Harvey, Sr. Park.

All city parks and pools in Tampa are open in summer 2020, so check individual locations through the Parks and Recreation department for hours and visiting information.

07 of 09

The Summer of Rum Festival

The Summer of Rum Festival is an annual event that takes place on the Saturday of Labor Day weekend and celebrates all things rum, from daiquiris to piña coladas. The 2020 event is scheduled for September 5 and tickets must be pre-purchased to attend. The festival takes place at the 25-acre Julian B. Lane Riverfront Park and is an all-day event, so be sure to pace yourself with the imbibing.

In addition to delicious rum drinks, enjoy live music, vendors selling local goods, and a curated Caribbean food market to accompany your beverages with specialties like jerk chicken and roti.

08 of 09

Labor Day Weekend Silent Disco

The Labor Day Silent Disco at Mastry's Brewing Co. is not scheduled to take place in 2020. Check the official webpage and Facebook for the most up-to-date information.

On the Saturday evening of Labor Day weekend, if you take a ride about 50 minutes west from Tampa to St. Pete Beach, you'll find a unique silent disco at Mastry's Brewing Co. Have fun dancing with headphones to three DJs playing tunes from Latin and reggaeton to modern dance and hip hop, among other musical styles.

Admission includes a set of headphones for the night and a full pour of craft beer.

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09 of 09

Rock the Yacht

Head out to the water on a Yacht Starship during Labor Day weekend for spectacular views and delicious meals. You can choose between a dinner cruise with sunset views or a Sunday brunch trip with unlimited mimosas. Cruises last two hours and you can choose to depart from Tampa or Clearwater, depending on the views you want. The Tampa boats offer a scenic view of downtown from the bay, while departing from Clearwater means you'll be out in the Gulf of Mexico.

Many of the typical activities, including live music and the dancefloor, are not open for cruises in 2020. Guests must also abide by a resort casual dress code, meaning a nice shirt and pants or dress shorts for men and a sundress, pants, or a skirt with a blouse for women.

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