21st Annual Islamorada Holiday Fest
PARADE THEME:
A Season for Kindness..
To Every Creature, Great or Small
“Big or Small, Kindness Fits All”
Friday, December 5, 2025
Founders Park, Islamorada
Event Schedule
Don’t miss out on the 2025 Ornament Auction – Start Bidding Here!
Holiday Fest will be held on the Great Lawn at Founders Park
The forecast calls for plenty of snow during the 21st Annual Islamorada Chamber of Commerce Holiday Fest, set for Friday, December 5, 2025, from 4 to 10 p.m. on the Great Lawn at Founders Park.
“Bundle up your family for one of the most exciting community events on the calendar,” said Chamber of Commerce President Rob Stober. “This will be a great time for everyone to kick off the holiday season.”
Magical snow blowing from the 35′ holiday tree will transform the park into a winter wonderland, creating the perfect setting for families and friends to gather and celebrate together.
The event’s star attraction, Snow Mountain, returns for its 21st year bringing snow fun to island kids! Featuring 30 tons of snow, it’s an enchanting experience for many children who are seeing snow for the very first time. Brand-new this year for the littlest visitors: Snowflake Mountain made of tons of whimsical, magical bubbles is sure to delight.
Snow is far from the only thing promised at Holiday Fest. At 7:30pm, the Holiday Parade will kick off with floats, antique cars and, of course, Santa himself.
Additional highlights include photos with Santa, live holiday stage performances, and the charming Mister Gingerbread Man and Miss Sugarplum Fairy contests. All participants will take the stage for a festive visit with Mrs. Claus and receive a bag of holiday treats. One boy and one girl will be crowned for 2025. Also returning is the Santa Paws Pet Parade, where furry companions take the stage in their most festive holiday attire – always a crowd favorite.
HOLIDAY BAZAAR
The festival also features the Holiday Bazaar, the perfect place to jump-start your holiday shopping. A highlight of the Bazaar is the online auction of handcrafted ornaments, created by more than 60 local artists. Each begins with a blank ceramic mold and transforms it into an original holiday treasure. The finished ornaments will be judged and displayed throughout the event, with online bidding open from November 30 at 12:30 p.m. until 9:00 p.m. on festival night. A portion of the proceeds benefits the local arts community. The Bazaar will also showcase local vendors offering unique gifts, handcrafted jewelry, and one-of-a-kind artisan crafts.
Returning this year is the Publix Holiday Sweet Shoppe, offering a tempting selection of sweet treats and giveaways. Stop by to enjoy a taste of the season. In addition to the Sweet Shoppe, a wide variety of savory food options will be available throughout the evening from local vendors.
HOLIDAY PARADE
The Chamber of Commerce is seeking more entrants for the Holiday Parade. For information, or if you would like to volunteer at Holiday Fest, call 305-664-4503 or stop by the Islamorada Chamber of Commerce & Visitors Center at MM87, bayside.
Parade Registration Form
At 7:30 p.m., the Holiday Parade will circle the Great Lawn, featuring festive floats, the CSHS Marching Band, antique cars, and, of course, Santa himself on the final float. Florida State Representative Jim Mooney, a lifelong Keys resident and former Islamorada mayor, will lead the parade as Grand Marshal. Organizations and individuals are encouraged to participate, with no fee to enter, and awards presented for 1st, 2nd, and 3rd place based on creativity and adherence to this year’s theme: “A Season for Kindness… to Every Creature Great and Small.
For more information on the parade, please call the Islamorada Chamber of Commerce & Visitors Center at 305-664-4503.
Mister Gingerbread Man and Miss Sugarplum Fairy Contest
Miss Sugarplum Fairy & Mister Gingerbread Man Contest Rules & Information
The Chamber is seeking contestants for this year’s Mister Gingerbread Man and Miss Sugarplum Fairy contest, which will take place at 5:00pm on the Great Lawn. Contestants must be under 8 years old and dressed up in their holiday outfit. They will be invited on stage to meet Mrs. Claus and tell her a holiday wish. One boy will be crowned Mister Gingerbread Man 2025 and one girl will be crowned Miss Sugarplum Fairy 2025. For more information, please contact the Chamber at 305-664-4503.
Ornament Competition to Add Color to Holiday Fest
More than sixty local artists are expected to take part in the ornament competition and silent auction at the 21st Annual Islamorada Holiday Festival, set for Friday, December 5, from 4 to 10 p.m. on the Great Lawn at Founders Park.
The festival, hosted by the Islamorada Chamber of Commerce, is one of the community’s most beloved holiday traditions. As part of the festival’s Holiday Gift Bazaar, each participating artist received an unfinished ceramic ornament to use as the base for their original creation. Beyond that, the only design limit is their imagination.
Jessica Ann, a local artist whose studio and gallery is at 151 Morada Way, is among the artists preparing for the event. A self-taught marine life artist, known for her vibrant, ocean-inspired artwork that brings people closer to the sea and encourages them to protect it, Jessica produces handpainted originals and in-house prints while minimizing waste and supporting local conservation initiatives. Her gallery in Islamorada showcases diverse collections, including the “Save the Glades” series, reflecting her dedication to preserving Florida’s unique ecosystems through art and community engagement.
The completed ornaments will be judged and displayed throughout the festival and available for purchase through a silent auction, which closes at 9:00 p.m. A portion of the proceeds will benefit the local arts community. Go to 32auctions.com/icc-2025 to bid on our favorite ornament!
For more information regarding the 2025 Islamorada Chamber Holiday Ornament Auction, please call the Chamber at 305-664-4503, email info@islamoradachamber.com, or stop by the Visitor Center at the entrance to Founders Park.
We can always use volunteers and helpers; please contact us if YOU can help!
Thank you to our Sponsors!
