Laura Young
ECB Publishing, Inc.
It's time for vendors, classic car buffs, parade participants, pageant hopefuls, photo snappers, pickle ball competitors and 5K runners to start things rolling toward the 2026 Watermelon Festival. The 75th Annual Watermelon Festival – organized by the Monticello-Jefferson County Chamber of Commerce since 1949 – promises loads of small town fun for the entire family. Eight days of festivities begin with pickle ball on May 16-17 and culminate with most events over June 19-20. The festival theme of “Stars, Slices and Stripes” celebrates the 75th anniversary of the event taking place in the same year as America's 250th Independence Day.
In addition to attending events, there are many other ways to become involved in this year's Watermelon Festival fun.
Sponsor the Festival
Individuals, businesses or organizations interested in becoming a Watermelon Festival Sponsor can find the 2026 Sponsorship Kit at the festival website, monticellowatermelonfestival.com. Sponsorship opportunities have both general and event-specific categories that range from $100 to $10,000. Sponsor recognitions reach 6,000 to 8,000 in-person visitors, with increasing exposure for higher levels of sponsorship. For more information, contact the Chamber at 850-997-5552.
Audition for the Kids Show
The MadCo production of “The Little Mermaid Jr.” will take place during the Watermelon Festival, and auditions are continuing Sunday, April 19 at 2 p.m. at MadCo Studio, located at 185 E. Walnut St., Monticello, Fla. Kids must be 8 or older to audition and should come dressed for a short dance audition and prepared with a memorized song from the musical genre. The fee to participate includes the costume. Rehearsals will begin the first week of May. For more information, see the Facebook page for Monticello Acting and Dance Company.
Nominate a Parade Grand Marshal
Deadline: Friday, May 8
The Parade Grand Marshal is presented to a resident of Jefferson County who has made a positive difference through leadership, community involvement, volunteerism and overall public service to the county. These activities should be outside the duties of the individual's regular job. Previous winners from the past five years are not eligible. To nominate someone deserving of this honor, complete a nomination form where the nominee's contributions to different aspects of community life can be listed. Nominations for Parade Grand Marshal will be accepted until noon on Friday, May 8. Nomination forms are available at the Chamber office (420 W. Washington St.) and online at monticellowatermelonfestival.com. The successful nominee will be decided by the Watermelon Festival Committee members and must be available to ride in the parade on Saturday, June 20. Please confirm that the nominee is willing to serve and is able to ride in the parade before submitting a nomination for them.
Ride/Walk in the Parade
Apply Now
The Watermelon Festival Parade takes place on Saturday, June 20, at 10 a.m. The parade committee welcomes participation from local and regional groups, businesses, agencies, services, representatives, churches and others whose entries are judged on their interpretation of the “Stars, Slices and Stripes” theme. The fee is $25 for each 30-foot space. The six winning categories are Best Merchant; Best Civic or Group; Most Unusual; Spirit Award; Best Theme; and Best In Show. (Late arrivals are ineligible for prizes). Detailed rules and regulations for parade entries can be found with the application at monticellowatermelonfestival.com. All applications are subject to the final approval of the parade committee. Questions can be directed to the Chamber office, 850-997-5552.
Be a Vendor
Apply Now
During the Watermelon Festival, downtown Monticello fills up with vendors selling food, arts and crafts to the crowds who come to enjoy the parade, platform events, car show, kids' show and more! The Chamber is accepting applications now. Each vendor space is 12' x 15' and applicants can request up to three spaces. Pricing is $120 for each regular space, with an upgrade to preferred space for $150 and $175 for food vendors. Apply at monticellowatermelonfestival.com, and direct any questions to the Chamber office, 850-997-5552.
Play in the Pickleball Tournament
The Watermelon Festival Pickleball Tournament takes place on May 16-17, to hopefully avoid some of the hot weather. To play one day costs $50; two days, $65. For secure a spot in the tournament, go to monticellowatermelonfestival.com. Direct any questions to the Chamber office, 850-997-5552.
Become a Pageant Contestant
The pageants take place on Saturday, June 6. Full-time residents of Jefferson County ages 3-21 who are interested in competing to be crowned a princess or queen can apply and submit the fee at monticellowatermelonfestival.com. Direct any questions to the Chamber office, 850-997-5552.
Enter a Photo Contest
The Watermelon Festival includes a Baby Photo Contest for children and a Pet Photo Contest with categories for cats, dogs and “others” (such as bunnies, birds, reptiles, etc.). Registration details will be available soon at monticellowatermelonfestival.com; direct any questions to the Chamber office, 850-997-5552.
Be in the Kids' Ride-On Parade
The Kids' Ride-On Parade happens on Friday, June 12 during the Kick-Off Block Party. This event is for youth riding bikes, trikes, wagons (pulled by parents), scooters and low-voltage powered toys. All contestants must be full-time residents of Jefferson County. There is no entry fee, and first through third place prizes will be given for Best Watermelon Decorations. Winners may also ride in the big parade the following Saturday. See monticellowatermelonfestival.com for regulations and the application, which must be received by Monday, June 5.
Do the Kiwanis 5K Watermelon Run & Walk
Bright and early on Saturday, June 13, registered participants can check in beginning at 7:30 a.m. at 325 Walnut St., and the race begins at 8:30 a.m. Runners will be “chip timed” by Gulf Winds Track Club. Link to the online registration portal from monticellowatermelonfestival.com. Questions concerning the race may be directed to Watermelonrun@gmail.com.
Show a Classic Car
The Third Annual Craig McCollum Memorial Watermelon Festival Car Show is Saturday, June 20, 8:30 a.m.-1:30 p.m. in the parking lot of Renasant Bank. Pre-registration will be available soon at monticellowatermelonfestival.com. The $20 fee is to be paid on the day of the show. Proceeds from the event will be donated to the Jefferson Tigers Baseball Team in Craig McCullum's memory. The show is sponsored by CarQuest Auto Parts / Morgan's Garage, and prizes are awarded for Best of Show, Cars 1920-1930, Cars 1931-1940, Cars 1941-1950, Cars 1951-1960, Cars 1961-1970, Cars 1971-1980, Cars 1981-1990, Cars 1991-2024, RestoMod, Trucks 1930-1960, Trucks 1961-2024, Best Motorcycle and Best Hot Rod. For more information, contact Don Romaine mpheonix1954@gmail.com or 850-242-2243.