by The Editors | July 3, 2024

Road Trip-Worthy Events This Summer

Parade through the streets of Key West, sample different brews in Tallahassee, cycle the hills of Mount Dora and more this summer.



Watch some of the nations biggest artists like Noah Kahan and JJ Grey & Mofro perform to help support the Live Wildly Foundation. Photography courtesy of Sing Out Loud.

Sing Out Loud Festival

St. Augustine
Sept. 21–22

Sing along with abandon—and possibly off-key­—in the Nation’s Oldest City with some of the highest-streamed musicians in the United States. Spanning across country, folk, alternative, pop and bluegrass genres, these 12 performers gather for one weekend in the open-air Francis Field to support the Live Wildly Foundation. This nonprofit organization combines entrepreneurship and conservation to find a sustainable, balanced way to protect the Florida Wildlife Corridor. Headliners include Eric Church, Noah Kahan, JJ Grey & Mofro, Norah Jones and more.

Greater Jacksonville Kingfish Tournament

July 10–20

Reel in a prize-winning catch at the largest kingfish tournament in the Southeast, and take a shot at one of the prizes, valued at more than $356,000. Fish from the dock, beach or offshore in five separate divisions and compete for the ultimate prize, a 28-foot center console Contender.

Tallahassee Beer Festival 

Aug. 10

Raise a glass to the capital city’s beer-filled bicentennial with over 100 national, regional and local brewers offering more than 300 fermentations to taste. After a little liquid courage, try your hand at axe-throwing, play some cornhole or run in the Beer Mile fun run.

Experience the thrill of a rodeo showdown this September in Pensacola. Photography courtesy of Bulls on the Beach.

Bulls on the Beach

Sept. 5–7

Swap your flip-flops for cowboy boots as the best professional bull riders across America take their talents to the soft white sand. Hosted by the Flora-Bama lounge, this rodeo showdown includes tie-down roping, live music and a mechanical bull.

Florida Fin Fest

Jacksonville Beach
Sept. 13–14

Wade into Jacksonville Beach’s free ocean conservation, education and music festival with a speaker series led by experts from Ocearch, an underwater virtual reality experience, several touch tanks, 10 food trucks and live music featuring Cimafunk, Shwayze, Honey Hounds and more.

Smokin’ in the Pines BBQ Festival

Sept. 20–21

Compete grill-to-grill at one of the most popular barbecue festivals in the South for over $15,000 in cash prizes. Pile up a plate with some of the best ribs, pulled pork, chicken and brisket in the state, jam to live Southern rock and sample from the Sauces of Honor Sauce Contest.

Celebrate the diverse arts and cultures of Pensacola with a range of events, from captivating art exhibitions to vibrant musical performances. Photography courtesy of Foo Foo Festival.

Foo Foo Festival

Oct. 31–Nov. 11

Kick back at this 12-day celebration of arts and culture, featuring myriad musical performances ranging from indie groups and classic jazz ensembles to soul singers and drag queens. Soak in art exhibitions, city-wide installations and the Pensacola Mural Festival.


Watch skilled ranch hands compete for the championship in reining, riding, and cow work. Photography courtesy of American Ranch Horse World Championship.

American Ranch Horse World Championship

July 3–13

Cheer on ranch hands as they compete for gold in reining, riding and cow work. Witness these riders execute herding and horsemanship in celebration of the spirit of ranching heritage.

Suncoast Ladies’ Classic Fishing Tournament

St. Petersburg
July 11–13

Face off with some of Florida’s fiercest fisherwomen and vie for up to $25,000 in prizes at this offshore competition, benefiting Ready for Life, a nonprofit for former foster youth.

Coke Zero Sugar 400

Aug. 24

Hear the roar of V8-engines as they race around the 2.5-mile track at the Daytona International Speedway. Meet the biggest names in NASCAR, sit front row at the grid and leave your mark by signing the starting line.

The perfect family event filled with all the fall feels to celebrate this upcoming September. Photography courtesy of Sweetfields Farm Fall Fest.

Sweetfields Farm Fall Fest

Sept. 28–Nov. 3

Traverse the corn maze, cruise the hay ride, pick a pumpkin and soak up all the fall feels in this bucolic setting. Top off the action with a bag of kettle corn, a plate of Papa P’s BBQ and a mason jar of apple cider.

Cycle Mount Dora

Mount Dora
Oct. 11–13

Attack off-road terrain on a 10-mile master ride or pedal with novices down Highland Street in celebration of 50 years of this two-wheeled fest, featuring a handful of courses and tracks with man-made jumps, flowing flats and burning uphill climbs. 

Experience the thrilling 1,000-hp boat race from St. Pete Pier. Photography courtesy of Monster Energy St. Pete Powerboat Grand Prix.

Monster Energy St. Pete Powerboat Grand Prix

St. Petersburg
Oct. 18–20

Post up at the new St. Pete Pier or from the streets of downtown St. Petersburg for a view of power and speed across Tampa Bay. Watch as Class One offshore 45-foot-long power boats rev their 1,000-horsepower engines and some of the sport’s elite competitors, like Rich Wyatt of df Young/Good Boy Vodka, throttle for $130,000 in prizes. 

Come get your jig on with live music and sauced up barbecue. Photography courtesy of Tampa Pig Jig.

Tampa Pig Jig

Oct. 19

Get barbecue sauced at this cook-off and music festival, where amateur smoke masters go head-to-head and national performers like Dierks Bentley and The Revivalists get their jig on. It’s all an effort to raise funds for a rare kidney disease.


Celebrate and remember the legendary singer-songwriter Jimmy Buffett this August in Key West. Photography courtesy of Just a Few Friends Key West.

Just a Few Friends Key West

Key West 
Aug. 29–Sept. 2

No other city could throw down for Jimmy Buffett like Key West, so it’s no surprise that it’s the location of the first annual, Just a Few Friends celebration. Spend Labor Day weekend honoring the legendary singer-songwriter who created an entire music genre inspired in part by the island’s bohemian culture. Immerse yourself in live music, a cheeseburger contest, margarita bar crawl and more, with the main event unfolding on the anniversary of Buffett’s death, Sept. 1. A lively second line procession will journey along iconic Duval Street and culminate in a concert on the Friends of Bubba stage. Proceeds from the weekend benefit the Bahama Village Music Program and Reef Relief.

Key West Marlin Tournament

Key West 
July 17–20

Hunt for a 500-pound marlin (and the $50,000 in prize money) or just get hooked watching the weigh-in at this world-class big game fishing tournament, taking place in conjunction with the annual Hemingway Days celebration.

Female Brew Fest

Fort Lauderdale  
Sept. 14

Toast to the women of the craft beer industry and enjoy endless pours from local and national brewers, like Tampa Bay Brewing Company, Florida Avenue Brewing Co. and Ardent Craft Ales, during this annual event featuring tastings, workshops, creative collabs and more.

Experience captivating music during this years Island Hopper Songwriter Fest on Captiva Island. Photography courtesy of Island Hopper Songwriter Fest.

Island Hopper Songwriter Fest

Captiva Island,
Fort Myers Beach
Sept. 20–29

Jam to 100 free performances by some of the top singer-songwriters from Nashville, Tennessee, and beyond, unfolding across four intimate venues during the 10th annual festival with headliners Scotty McCreery and Jeffrey Steele.

18th Annual Treasure Coast International Film Festival

Fort Pierce,
Port St. Lucie 
Oct. 16–20

Screens will light up with more than 45 independent films, live music and art. Audiences vote on their favorite flicks, which will compete in Best Feature Film and Best Documentary. 

Racing at 200 mph for a shot at the Championship 4. Photography courtesy of NASCAR.

NASCAR Cup Series Race

Oct. 27

NASCAR’s top drivers race 267 laps around the 1.5-mile track at speeds nearing 200 mph in this playoff series for a spot in the Championship 4. The only thing hotter is the party atmosphere. 

Fort Lauderdale International Boat Show

Fort Lauderdale
Oct. 30–Nov. 3

Walk the docks lined with more than 1,300 of the latest vessels, including national and global debuts, at the world’s largest in-water boat show. This sea soiree spans seven locations, including Bahia Mar Yachting Center, Las Olas Marina and Pier Sixty-Six Marina.