Islamorada's Holiday Fest Turns 22 Under New Chamber Leadership, and the Weekend Builds Around It

"Holiday Fest is my baby," Judy Hull told Keys Weekly this month. "I couldn't imagine that we didn't have a holiday celebration. It was created as a community event, not a fundraiser."

Hull has retired after 21 years as executive director of the Islamorada Chamber of Commerce, as the Florida Keys Free Press reported. Katie Brennan succeeds her. On Friday, December 4, the 22nd Annual Holiday Fest fills the Great Lawn at Founders Park for the first time since 2005 with someone other than its creator leading the Chamber. From Indian Waterways, the park is a short drive down the Overseas Highway. Holiday Fest also sits in the middle of the season's most crowded stretch of Upper Keys events, so that one night shapes most of December.

The Rules Hull Wrote Are Still the Rules

Most of what people expect from Holiday Fest goes back to choices Hull made in her first year. Keys Weekly reports that the festival has been held on the first Friday of December since 2005. It has a new theme every year, a parade, a tree that blows "snow," a holiday bazaar and an auction of ornaments painted by artists. The ornament idea came from an earlier job, where she had artists paint Easter eggs. The first tree was 30 feet tall, paid for with help from sponsors, and five feet were added in later years.

The snow has always been the hardest part to pull off. According to the same profile, 30 tons of ice and a chipper arrive each year on three semi trucks. Hull recalled the one year a semi broke down in Homestead and the snow mound never happened. The 2026 plan keeps all of it. The Chamber's Holiday Fest page promises snow blowing from the 35-foot tree and the return of Snow Mountain, with 30 tons of snow, for its 22nd year.

The Chamber also lists Snowflake Mountain, a mound of bubbles for the youngest visitors, next to the snow.

How the Night Runs on December 4

The festival runs from 4 to 10 p.m. on the Great Lawn. The Chamber's page labels this year's parade theme "Deck the Glades," under the banner Everglades Holiday Magic, though its parade awards section still names a different theme line, so float builders should confirm with the Chamber. Here is how the evening is laid out:

1. 4 p.m. The festival opens with Snow Mountain, the Holiday Bazaar, local food vendors and the Publix Holiday Sweet Shoppe.
2. 5 p.m. The Mister Gingerbread Man and Miss Sugarplum Fairy contest starts on the Great Lawn. It is open to children under 8 in holiday outfits, who go on stage to tell Mrs. Claus a holiday wish.
3. Through the evening Santa photos, live holiday performances and the Santa Paws Pet Parade, where pets go on stage in holiday costumes.
4. 7:30 p.m. The Holiday Parade circles the Great Lawn with floats, the CSHS Marching Band, antique cars and Santa on the last float. State Rep. Jim Mooney, a lifelong Keys resident and former Islamorada mayor, leads it as Grand Marshal.
5. 9 p.m. Bidding closes on the ornament auction.

The parade still takes entries, and entering is free. Awards go to first, second and third place based on creativity and how well an entry fits the theme. Anyone who wants to enter a float or volunteer can call the Chamber at 305-664-4503 or stop by the Islamorada Chamber of Commerce & Visitors Center at MM 87, bayside.

The Auction Starts Five Days Early

For many people, Holiday Fest starts on Sunday, November 29. Online bidding on the ornaments opens that day at 12:30 p.m. and stays open until 9 p.m. on festival night. More than 60 local artists each start with the same blank ceramic ornament and make something original from it. The finished pieces are judged and displayed during the festival, and part of the proceeds goes to the local arts community.

The Chamber names one of this year's artists. Jessica Ann is a self-taught marine life artist whose studio and gallery are at 151 Morada Way. Her collections there include a "Save the Glades" series. That series fits a year with "Deck the Glades" as the theme.

Morada Way is also a good first stop before the auction. The Morada Way Art Walk falls on Thursday, November 19, ten days before bidding opens. The Morada Way Arts & Cultural District holds the walk every third Thursday from 6 to 9 p.m., with late gallery openings, local artists, live music and food. Anyone who wants to see the artists' regular work before bidding on their ornaments can do it in one evening on a single street.

Saturday Morning Picks Up the Weekend

Holiday Fest ends at 10 p.m. Friday, and the Garden Club of the Upper Keys Holiday Market opens at 9 the next morning. The market runs Saturday, December 5, from 9 a.m. to 4 p.m. at the Francis Tracy Garden Center, 94040 Overseas Highway in Tavernier. The Garden Club expects more than 40 vendors selling food, plants, jewelry, clothing and crafts, and the club will sell garden-related items from its clubhouse.

That puts the season's two largest community markets less than 24 hours apart, both close to Plantation Key. The Holiday Bazaar on Friday night features handcrafted jewelry, artisan crafts and the ornaments. The Garden Club market on Saturday leans toward plants and garden goods. Shopping both covers a lot of a holiday list without leaving the Upper Keys.

The Weeks on Either Side

Once Holiday Fest's weekend is set, the rest of the season falls into place around it. The calendar runs from mid-November to the week before Christmas:

Reef Revival Fest is the free event the night after the November art walk. Mote Marine Laboratory lists live music, food trucks, Florida Keys Brewing Company beer, a kids' zone, tours of the coral nursery, micro-fragmentation workshops and a mechanical shark ride.

The boat parades come after Holiday Fest. The Key Largo Boat Parade lines up at 6:30 p.m. on December 12 and starts at 7:30 at Dusenbury Creek, green channel marker 41, then heads north along the shoreline to Stillwright Point. The Key Largo Sunset Rotary Club hosts it, with shoreside events listed at Sundowners, 103900 Overseas Highway, from 5 to 9 p.m. Closer to home, Papa Joe's Waterfront lists its Deck the Hulls Holiday Boat Parade for Saturday, December 19. The restaurant hasn't posted a start time, so check with them closer to the date.

Hull told Keys Weekly she wanted Holiday Fest to be a community event, not a fundraiser. This year's program still follows that plan, starting at 4 p.m. on Friday, December 4, on the Great Lawn at Founders Park.

As a neighbor who serves on Islamorada's parks and recreation advisory committee, I'm glad to see Founders Park host one of the village's longest-running traditions again. If you'd like to talk about life along this stretch of the Keys, during the holidays or any other time, Alina Davis is always happy to hear from you. Let's Connect.